JP2002234853A

JP2002234853A - Optically active compound, liquid crystal composition containing the same and liquid crystal element

Info

Publication number: JP2002234853A
Application number: JP2001032682A
Authority: JP
Inventors: Osamu Yokokoji; 修横小路; Takeshi Koike; 毅小池; Masaki Oiwa; 正起大岩; Tamon Tachibana; 多聞橘
Original assignee: Seimi Chemical Co Ltd
Current assignee: Seimi Chemical Co Ltd
Priority date: 2001-02-08
Filing date: 2001-02-08
Publication date: 2002-08-23
Anticipated expiration: 2021-02-08
Also published as: JP4668431B2

Abstract

PROBLEM TO BE SOLVED: To provide a new optically active compound which has large spiral mobile power and large dielectric constant anisotropy, to provide a liquid crystal composition containing the compound, and to provide a liquid crystal electrooptical element using the composition. SOLUTION: The optically active compound represented by formula (1) [A is CH2 or the like; B1, B2 and B3 are each COO or the like; D1 and D2 are each a non-substituted 1,4-phenyl group or the like; X is CH3 or the like; Y1, Y2, Y3 and Y4 are each F or H, provided that one of Y1, Y2, Y3 and Y4 is F; Z is CN or the like; (n) is 0 or 1; C* is an asymmetric carbon atom].

Description

DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【発明の属する技術分野】本発明は、新規な光学活性化
合物、該化合物を含む液晶組成物、および該組成物を用
いた液晶電気光学素子（以下、液晶素子ともいう。）に
関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel optically active compound, a liquid crystal composition containing the compound, and a liquid crystal electro-optical device using the composition (hereinafter, also referred to as a liquid crystal device).

【０００２】[0002]

【従来の技術】近年、液晶光学素子は、ＯＡ機器用表示
装置をはじめ、測定器、自動車用計器、家電製品用表示
装置、時計、電卓等種々の用途に広範に使用されてい
る。かかる液晶電気光学素子は、それぞれ表面に透明電
極、中間保護膜、および液晶配向膜が形成された一対の
透明基板を、一定の距離を隔てて配置し、その基板間に
液晶材料を封入した構造になっており、電極から液晶材
料に電圧を印加し、液晶材料の配列状態を変化させて光
学的な性質を変えることにより、所謂光スイッチング素
子として機能している。2. Description of the Related Art In recent years, liquid crystal optical elements have been widely used in various applications such as display devices for OA equipment, measuring instruments, automotive instruments, display devices for home appliances, watches, and calculators. Such a liquid crystal electro-optical element has a structure in which a pair of transparent substrates each having a transparent electrode, an intermediate protective film, and a liquid crystal alignment film formed on a surface thereof are arranged at a fixed distance, and a liquid crystal material is sealed between the substrates. By applying a voltage to the liquid crystal material from the electrodes and changing the arrangement state of the liquid crystal material to change the optical properties, it functions as a so-called optical switching element.

【０００３】一方、ツイストネマチック（ＴＮ）型およ
びスーパーツイストネマチック（ＳＴＮ）型液晶表示素
子には、均一なツイスト配向を達成するために、少量の
光学活性化合物（カイラル剤）を添加した液晶組成物が
知られている。現在幅広く用いられている、カイラル剤
である光学活性化合物には、例えば、下式（ＣＮ）で表
される化合物、式（ＣＢ−１５）で表される化合物、ま
たは下式（Ｓ−８１１）で表される化合物などがある。On the other hand, twisted nematic (TN) type and super twisted nematic (STN) type liquid crystal display devices include a liquid crystal composition to which a small amount of an optically active compound (chiral agent) is added in order to achieve uniform twist alignment. It has been known. Optically active compounds that are currently widely used as chiral agents include, for example, a compound represented by the following formula (CN), a compound represented by the formula (CB-15), or a compound represented by the following formula (S-811) And the like.

【０００４】[0004]

【化５】 Embedded image

【０００５】光学活性化合物を液晶組成物に添加した場
合に誘起されるヘリカルピッチ長は、化合物固有のらせ
ん誘起力によって決まり、また、添加量にほぼ比例す
る。らせん誘起力が小さい光学活性化合物ほど、誘起さ
れるヘリカルピッチ長が長く、添加量を多くしなければ
ならない。一般に、光学活性化合物の添加量を多くする
と、添加前と比較して、液晶材料としての性能は低下
し、粘度の上昇、応答速度の低下、駆動電圧の上昇、等
方相転移温度の低下、ネマチック相、コレステリック相
などの特定の相を示す温度範囲の縮小などの問題が生じ
る。そのため、らせん誘起力の大きな光学活性化合物が
求められている。[0005] The helical pitch length induced when an optically active compound is added to a liquid crystal composition is determined by the helical inducing force inherent to the compound, and is almost proportional to the amount added. The smaller the helical inducing force, the longer the helical pitch length to be induced and the larger the amount to be added. In general, when the added amount of the optically active compound is increased, the performance as a liquid crystal material is reduced as compared with before the addition, the viscosity is increased, the response speed is reduced, the driving voltage is increased, the isotropic phase transition temperature is reduced, Problems such as reduction of the temperature range showing a specific phase such as a nematic phase and a cholesteric phase occur. Therefore, an optically active compound having a large helical inducing force is required.

【０００６】一方、近年、ネマチック液晶組成物に光学
活性化合物を大量（１０〜３０重量％程度）に添加した
コレステリック液晶またはカイラルネマチック液晶と呼
ばれる組成物を用い、コレステリック液晶が液晶材料の
平均屈折率とヘリカルピッチ長との積である波長の光を
選択反射する現象を利用した反射コレステリック型（カ
イラルネマチック型）液晶表示素子が注目されている。
この反射コレステリック型（カイラルネマチック型）液
晶表示素子は、偏光板およびカラーフィルターを必要と
しないため、光の利用効率が高く、また、表示状態が保
持される（メモリー性）ため、電圧の印加は表示の切り
替え（書き込み）時のみでよく、低消費電力であるとい
う優れた特長を持っている。On the other hand, in recent years, a composition called a cholesteric liquid crystal or a chiral nematic liquid crystal obtained by adding a large amount (about 10 to 30% by weight) of an optically active compound to a nematic liquid crystal composition has been used, and the cholesteric liquid crystal has an average refractive index of the liquid crystal material. A reflective cholesteric (chiral nematic) liquid crystal display device utilizing a phenomenon of selectively reflecting light having a wavelength that is the product of the helical pitch length and the helical pitch length has attracted attention.
This reflective cholesteric (chiral nematic) liquid crystal display element does not require a polarizing plate and a color filter, and thus has high light use efficiency and maintains a display state (memory property). It only has to be used when switching (writing) the display, and has an excellent feature of low power consumption.

【０００７】しかし、光学活性化合物を大量に添加する
ため、コレステリック液晶（カイラルネマチック液晶）
組成物の粘度は大きく、そのために応答速度が遅い、駆
動電圧が高いなどの問題点を有している。液晶素子の駆
動電圧と液晶組成物の誘電率異方性（Δε）には相関関
係があり、誘電率異方性の大きい液晶組成物は、低い駆
動電圧で駆動することができる。反射コレステリック型
（カイラルネマチック型）液晶素子の低駆動電圧化のた
めには、誘電率異方性の大きいネマチック液晶組成物と
ともに、誘電率異方性の大きい光学活性化合物が求めら
れている。However, since a large amount of an optically active compound is added, a cholesteric liquid crystal (chiral nematic liquid crystal) is used.
The viscosity of the composition is high, which causes problems such as low response speed and high driving voltage. There is a correlation between the driving voltage of the liquid crystal element and the dielectric anisotropy (Δε) of the liquid crystal composition, and a liquid crystal composition having a large dielectric anisotropy can be driven at a low driving voltage. In order to reduce the driving voltage of a reflection cholesteric (chiral nematic) liquid crystal device, an optically active compound having a large dielectric anisotropy is required together with a nematic liquid crystal composition having a large dielectric anisotropy.

【０００８】先に、本出願人は、特開平１１−２５５６
７５号公報として、粘性が小さくヘリカルねじれ能が大
であり、らせん誘起力が大きい光学活性化合物を提案し
た。しかし、かかる特開平１１−２５５６７５号公報に
具体的に開示されている光学活性化合物は、特に、反射
コレステリック型（カイラルネマチック型）液晶素子の
ためには、上記らせん誘起力が不充分であり、もっと大
きいらせん誘起力が求められるとともに、さらに、上記
特開平１１−２５５６７５号公報には未だ認識されてい
ない光学活性化合物の誘電率異方性が大きい光学活性化
合物が求められている。First, the applicant of the present invention disclosed in Japanese Patent Application Laid-Open No. H11-2556.
No. 75 proposes an optically active compound having a small viscosity, a large helical twisting ability, and a large helical inducing force. However, the optically active compound specifically disclosed in Japanese Patent Application Laid-Open No. H11-255675 is insufficient in the helical inducing force, particularly for a reflective cholesteric (chiral nematic) liquid crystal element. A larger helical inducing force is required, and an optically active compound having a large dielectric anisotropy of an optically active compound which is not yet recognized in Japanese Patent Application Laid-Open No. H11-255675 is required.

【０００９】[0009]

【発明が解決しようとする課題】本発明の目的は、らせ
ん誘起力が大きく、誘電率異方性（Δε）が大きく、カ
イラル剤としても著しく優れた性能を発揮する新規の光
学活性化合物、かかる光学活性化合物を含有する、低電
圧での駆動が可能な液晶組成物、及びかかる液晶組成物
を使用した、特に、ＳＴＮ型またはコレステリック型
（カイラルネマチック型）液晶素子を提供する。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel optically active compound which has a large helical inducing force, a large dielectric anisotropy (.DELTA..epsilon.) And a remarkably excellent performance as a chiral agent. Provided are a liquid crystal composition containing an optically active compound, which can be driven at a low voltage, and an STN or cholesteric (chiral nematic) liquid crystal device using the liquid crystal composition.

【００１０】[0010]

【課題を解決するための手段】本発明者らは研究を重ね
たところ、下式（１）で表される光学活性化合物（以
下、式（１）で表される光学活性化合物を化合物（１）
とも記す。）、該光学活性化合物を含む液晶組成物、お
よび該液晶組成物を用いた液晶素子が上記課題を充分に
解決することが見出された。Means for Solving the Problems The inventors of the present invention have conducted studies and found that an optically active compound represented by the following formula (1) (hereinafter, an optically active compound represented by the formula (1) is compound (1) )
Also described. ), A liquid crystal composition containing the optically active compound, and a liquid crystal device using the liquid crystal composition have been found to sufficiently solve the above problems.

【００１１】[0011]

【化６】ただし、式（１）中の記号は、それぞれ、以下の意味を
表す。Ａ：−ＣＨ₂−または−ＣＯ−。Ｂ₁、Ｂ₂、Ｂ₃：相互に独立して、−ＣＯＯ−、−ＯＣ
Ｏ−、−ＣＨ₂ＣＨ₂−、−ＣＨ₂Ｏ−、−ＯＣＨ₂−、−
ＣＦ＝ＣＦ−、−ＣＦ₂Ｏ−または単結合。Ｄ₁、Ｄ₂：相互に独立して、非置換の１，４−フェニル
基、非置換のトランス−１，４−シクロヘキシレン基ま
たは単結合。Ｘ：−ＣＨ₃、−ＣＨＦ₂、−ＣＨ₂Ｆ、−ＣＦ₃またはフ
ッ素原子。Ｙ₁、Ｙ₂、Ｙ₃、Ｙ₄：相互に独立して、フッ素原子また
は水素原子。ただし、Ｙ ₁、Ｙ₂、Ｙ₃、Ｙ₄のうち一つは
フッ素原子。Ｚ：−ＣＮ、−ＣＦ₃、−ＯＣＦ₃、−ＳＦ₅またはフッ
素原子。ｎ：０または１。Ｃ^*：不斉炭素原子。Embedded imageHowever, the symbols in the formula (1) have the following meanings, respectively.
Represent. A: -CH_Two-Or -CO-. B₁, B_Two, B_Three: Independently of one another, -COO-, -OC
O-, -CH_TwoCH_Two-, -CH_TwoO-, -OCH_Two−, −
CF = CF-, -CF_TwoO- or a single bond. D₁, D_Two: Independently of each other, unsubstituted 1,4-phenyl
Group, unsubstituted trans-1,4-cyclohexylene group
Or a single bond. X: -CH_Three, -CHF_Two, -CH_TwoF, -CF_ThreeOr
Nitrogen atom. Y₁, Y_Two, Y_Three, Y_Four: Independently of each other, a fluorine atom or
Is a hydrogen atom. Where Y ₁, Y_Two, Y_Three, Y_FourOne of them
Fluorine atom. Z: -CN, -CF_Three, -OCF_Three, -SF_FiveOr
Elementary atom. n: 0 or 1. C^*: Asymmetric carbon atom.

【００１２】[0012]

【発明の実施の形態】［式（１）の説明］化合物（１）
は、その構造中に不斉炭素（Ｃ^*）を含む光学活性な化
合物である。不斉炭素に結合する基の絶対配置は、Ｒま
たはＳのいずれであってもよい。化合物（１）におい
て、Ａは、−ＣＨ₂−または−ＣＯ−である。なかで
も、化合物の安定性、信頼性の点から−ＣＨ₂−が好ま
しい。Ｂ₁、Ｂ₂、Ｂ₃は、相互に独立して、−ＣＯＯ
−、−ＯＣＯ−、−ＣＨ₂ＣＨ₂−、−ＣＨ₂Ｏ−、−Ｏ
ＣＨ₂−、−ＣＦ＝ＣＦ−、−ＣＦ₂Ｏ−または単結合で
ある。なかでも、誘電率異方性の大きさの点から、−Ｃ
ＯＯ−が好ましく、化合物の安定性・信頼性の点から単
結合が特に好ましい。Ｄ₁、Ｄ₂は、相互に独立して、非
置換の１，４−フェニル基、非置換のトランス−１，４
−シクロヘキシレン基、または単結合である。なかで
も、粘性の小ささ点から単結合が特に好ましい。Ｘは、
−ＣＨ₃、−ＣＨＦ₂、−ＣＨ₂Ｆ、−ＣＦ₃またはフッ素
原子である。なかでも、らせん誘起力の大きさの点で−
ＣＨ₃が特に好ましい。Ｙ₁、Ｙ₂、Ｙ₃、Ｙ₄は、相互に
独立して、フッ素原子または水素原子である。ただし、
Ｙ₁、Ｙ₂、Ｙ₃、Ｙ₄のうち一つはフッ素原子である。な
かでも、誘電率異方性の大きさの点から、Ｙ₃、Ｙ₄のう
ちの一つ以上がフッ素原子であることが好ましく、
Ｙ₃、Ｙ₄がともにフッ素原子であることが特に好まし
い。Ｚは、−ＣＮ、−ＣＦ₃、−ＯＣＦ₃、−ＳＦ₅また
はフッ素原子である。なかでも、化合物の安定性・信頼
性の点からフッ素原子、−ＣＦ₃が好ましく、誘電率異
方性の大きさの点から−ＣＮが特に好ましい。ｎは、０
または１である。誘電率異方性の大きさの点から１が好
ましい。DESCRIPTION OF THE INVENTION [Description of Formula (1)] Compound (1)
Is an optically active compound containing an asymmetric carbon (C ^* ) in its structure. The absolute configuration of the group bonded to the asymmetric carbon may be either R or S. In the compound (1), A is, -CH ₂ - is or -CO-. Among them, the stability of the compound, -CH ₂ from the viewpoint of reliability - are preferred. B ₁ , B ₂ , and B ₃ are each independently —COO
-, - OCO -, - CH 2 CH 2 -, - CH 2 O -, - O
CH ₂ —, —CF ＝ CF—, —CF ₂ O— or a single bond. Above all, from the viewpoint of the magnitude of dielectric anisotropy, -C
OO- is preferable, and a single bond is particularly preferable in terms of stability and reliability of the compound. D ₁ and D ₂ each independently represent an unsubstituted 1,4-phenyl group or an unsubstituted trans-1,4
-A cyclohexylene group or a single bond. Among them, a single bond is particularly preferable from the viewpoint of low viscosity. X is
—CH ₃ , —CHF ₂ , —CH ₂ F, —CF ₃ or a fluorine atom. Above all, in terms of the magnitude of the helical induction force-
CH ₃ is particularly preferred. Y ₁ , Y ₂ , Y ₃ , and Y ₄ are each independently a fluorine atom or a hydrogen atom. However,
One of Y ₁ , Y ₂ , Y ₃ and Y ₄ is a fluorine atom. Among them, from the viewpoint of the magnitude of the dielectric anisotropy, it is preferable that one or more of Y ₃ and Y ₄ be a fluorine atom,
It is particularly preferred that both Y ₃ and Y ₄ are fluorine atoms. Z _{_{is, -CN, -CF 3, -OCF 3}} , a -SF ₅ or a fluorine atom. Among them, the stability and reliability fluorine atom from the viewpoint of the compounds is preferably -CF _3, is -CN terms of the magnitude of the dielectric anisotropy particularly preferred. n is 0
Or 1. 1 is preferable in terms of the magnitude of the dielectric anisotropy.

【００１３】また、本発明の光学活性化合物（１）は、
液晶材料として、１種または２種以上を使用することが
できる。該化合物（１）を２種以上使用する場合には、
液晶組成物に添加した場合に誘起されるらせん方向が同
一であるものを組み合わせて使用することが好ましい。Further, the optically active compound (1) of the present invention comprises
One or two or more liquid crystal materials can be used. When two or more types of the compound (1) are used,
It is preferable to use those having the same helix direction induced when added to the liquid crystal composition in combination.

【００１４】以下、本発明の光学活性化合物（１）の具
体例を順に説明する。なお、本明細書を通じて、−Ｃｙ
−は非置換のトランス−１，４−シクロヘキシレン基、
−Ｐｈ−は非置換の１，４−フェニレン基、−Ｐｈ^F−
は２−フルオロ−１，４−フェニレン基（式（５））、
−Ｐｈ^FF−は２，６−ジフルオロ−１，４−フェニレン
基（式（６））を示す。ただし、式（５）および式
（６）においては、Ｚに近い側を１位とし、フッ素置換
基の位置は下式に示す通りである。これらを総称して
「環基」と記載する。式（１）において、環基の数は、
好ましくは２〜５でありうるが、相転移温度および粘性
が小さい点から、３または４が好ましく、３が特に好ま
しい。Hereinafter, specific examples of the optically active compound (1) of the present invention will be described in order. Note that throughout this specification, -Cy
-Is an unsubstituted trans-1,4-cyclohexylene group,
-Ph- is unsubstituted 1,4-phenylene group, -Ph ^F -
Is a 2-fluoro-1,4-phenylene group (formula (5)),
-Ph ^FF -represents a 2,6-difluoro-1,4-phenylene group (formula (6)). However, in the formulas (5) and (6), the side near Z is the 1-position, and the position of the fluorine substituent is as shown in the following formula. These are collectively referred to as “ring group”. In the formula (1), the number of ring groups is
It may be preferably 2 to 5, but is preferably 3 or 4, and particularly preferably 3 in view of the low phase transition temperature and viscosity.

【００１５】[0015]

【化７】 Embedded image

【００１６】以下、式（１）で表される化合物の具体例
を、環基の数およびＺの種類により分類し、順に例示す
る。なお、本明細書を通じて、不斉炭素原子は単にＣと
も記述する。Hereinafter, specific examples of the compound represented by the formula (1) are classified according to the number of ring groups and the type of Z, and are exemplified in order. In addition, throughout this specification, an asymmetric carbon atom is also simply described as C.

【００１７】＜環基の数が３である化合物の具体例＞Ｚ
＝ＣＮである化合物の好ましい具体例は、下記化合物が
挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^FF-CN H-Ph-CH(CF₃)-CH₂-Ph-Ph^FF-CN H-Ph-CHF-CH₂-Ph-Ph^FF-CN H-Ph-CH(CH₃)-CO-Ph-Ph^FF-CN H-Ph-CH(CF₃)-CO-Ph-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^FF-CN H-Ph-CH(CF₃)-CH₂-Ph-COO-Ph^FF-CN H-Ph-CHF-CH₂-Ph-COO-Ph^FF-CN H-Ph-CH(CH₃)-CO-Ph-COO-Ph^FF-CN H-Ph-CH(CF₃)-CO-Ph-COO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^FF-CN H-Ph-CH(CF₃)-CH₂-Ph-OCO-Ph^FF-CN H-Ph-CHF-CH₂-Ph-OCO-Ph^FF-CN H-Ph-CH(CH₃)-CO-Ph-OCO-Ph^FF-CN H-Ph-CH(CF₃)-CO-Ph-OCO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^FF-CN H-Ph-CH(CF₃)-CH₂-Ph-CH₂CH₂-Ph^FF-CN H-Ph-CHF-CH₂-Ph-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CO-Ph-CH₂CH₂-Ph^FF-CN H-Ph-CH(CF₃)-CO-Ph-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^FF-CN H-Ph-CH(CF₃)-CH₂-Ph-CH₂O-Ph^FF-CN H-Ph-CHF-CH₂-Ph-CH₂O-Ph^FF-CN H-Ph-CH(CH₃)-CO-Ph-CH₂O-Ph^FF-CN H-Ph-CH(CF₃)-CO-Ph-CH₂O-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^FF-CN H-Ph-CH(CF₃)-CH₂-Ph-OCH₂-Ph^FF-CN H-Ph-CHF-CH₂-Ph-OCH₂-Ph^FF-CN H-Ph-CH(CH₃)-CO-Ph-OCH₂-Ph^FF-CN H-Ph-CH(CF₃)-CO-Ph-OCH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^FF-CN H-Ph-CH(CF₃)-CH₂-Ph-CF=CF-Ph^FF-CN H-Ph-CHF-CH₂-Ph-CF=CF-Ph^FF-CN H-Ph-CH(CH₃)-CO-Ph-CF=CF-Ph^FF-CN H-Ph-CH(CF₃)-CO-Ph-CF=CF-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^FF-CN H-Ph-CH(CF₃)-CH₂-Ph-CF₂O-Ph^FF-CN H-Ph-CHF-CH₂-Ph-CF₂O-Ph^FF-CN H-Ph-CH(CH₃)-CO-Ph-CF₂O-Ph^FF-CN H-Ph-CH(CF₃)-CO-Ph-CF₂O-Ph^FF-CN<Specific examples of the compound having 3 ring groups> Z
Preferred specific examples of the compound where = CN include the following compounds. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^F -CN H-Ph- CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^FF -CN H-Ph-CH (CF ₃ ) -CH ₂ -Ph-Ph ^FF -CN H-Ph-CHF-CH ₂ -Ph-Ph ^FF -CN H-Ph-CH (CH ₃ )- CO-Ph-Ph ^FF -CN H-Ph-CH (CF ₃ ) -CO-Ph-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^F -CN H-Ph -CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO- Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^FF -CN H- Ph-CH (CF ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CN H-Ph-CHF-CH ₂ -Ph-COO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CO-Ph- COO-Ph ^FF -CN H-Ph-CH (CF ₃ ) -CO-Ph-COO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^F -CN H-Ph -CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF - OCO-Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^FF -CN H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph ^FF -CN H-Ph-CH (CF ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -CN H-Ph-CHF-CH ₂ -Ph-OCO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CO-Ph-OCO-Ph ^FF- CN H-Ph-CH (CF ₃ ) -CO-Ph-OCO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CHF-CH _2- Ph-CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CF ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O- Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O- Ph ^FF -CN H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^FF -CN H-Ph-CHF-CH ₂ -Ph-CH ₂ O-Ph ^FF -CN H-Ph- CH (CH ₃ ) -CO-Ph-CH ₂ O-Ph ^FF -CN H-Ph-CH (CF ₃ ) -CO-Ph-CH ₂ O-Ph ^FF -CN H-Ph-CH (CH ₃ )- CH ₂ -Ph-OCH ₂ -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^F- CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^F -CN H-Ph -CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^FF -CN H-Ph-CH (CF ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^FF -CN H-Ph-CHF-CH ₂ -Ph-OCH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -CN H-Ph-CH (CF ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF = CF-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph-CN H- Ph-CH (CH ₃ ) -CH ₂ -Ph-CF = CF-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph-CN H-Ph-CH ( CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph ^FF -CN H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CF = CF-Ph ^FF -CN H-Ph-CHF-CH ₂ -Ph-CF = CF-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CO-Ph-CF = CF-Ph ^FF -CN H-Ph-CH (CF ₃ ) -CO-Ph-CF = CF-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^F -CN H- Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -CN H-Ph-CH ( CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph-CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph ^FF -CN H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -CN H-Ph-CHF-CH ₂ -Ph-CF ₂ O -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CO-Ph-CF ₂ O-Ph ^FF -CN H-Ph-CH (CF ₃ ) -CO-Ph-CF ₂ O-Ph ^FF -CN

【００１８】Ｚ＝ＣＦ₃である化合物の好ましい具体例
は、下記化合物が挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^FF-CF₃ H-Ph-CH(CF₃)-CH₂-Ph-Ph^FF-CF₃ H-Ph-CHF-CH₂-Ph-Ph^FF-CF₃ H-Ph-CH(CH₃)-CO-Ph-Ph^FF-CF₃ H-Ph-CH(CF₃)-CO-Ph-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^FF-CF₃ H-Ph-CH(CF₃)-CH₂-Ph-COO-Ph^FF-CF₃ H-Ph-CHF-CH₂-Ph-COO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CO-Ph-COO-Ph^FF-CF₃ H-Ph-CH(CF₃)-CO-Ph-COO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^FF-CF₃ H-Ph-CH(CF₃)-CH₂-Ph-OCO-Ph^FF-CF₃ H-Ph-CHF-CH₂-Ph-OCO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CO-Ph-OCO-Ph^FF-CF₃ H-Ph-CH(CF₃)-CO-Ph-OCO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CF₃)-CH₂-Ph-CH₂CH₂-Ph^FF-CF₃ H-Ph-CHF-CH₂-Ph-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CO-Ph-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CF₃)-CO-Ph-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^FF-CF₃ H-Ph-CH(CF₃)-CH₂-Ph-CH₂O-Ph^FF-CF₃ H-Ph-CHF-CH₂-Ph-CH₂O-Ph^FF-CF₃ H-Ph-CH(CH₃)-CO-Ph-CH₂O-Ph^FF-CF₃ H-Ph-CH(CF₃)-CO-Ph-CH₂O-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^FF-CF₃ H-Ph-CH(CF₃)-CH₂-Ph-OCH₂-Ph^FF-CF₃ H-Ph-CHF-CH₂-Ph-OCH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CO-Ph-OCH₂-Ph^FF-CF₃ H-Ph-CH(CF₃)-CO-Ph-OCH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^FF-CF₃ H-Ph-CH(CF₃)-CH₂-Ph-CF=CF-Ph^FF-CF₃ H-Ph-CHF-CH₂-Ph-CF=CF-Ph^FF-CF₃ H-Ph-CH(CH₃)-CO-Ph-CF=CF-Ph^FF-CF₃ H-Ph-CH(CF₃)-CO-Ph-CF=CF-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^FF-CF₃ H-Ph-CH(CF₃)-CH₂-Ph-CF₂O-Ph^FF-CF₃ H-Ph-CHF-CH₂-Ph-CF₂O-Ph^FF-CF₃ H-Ph-CH(CH₃)-CO-Ph-CF₂O-Ph^FF-CF₃ H-Ph-CH(CF₃)-CO-Ph-CF₂O-Ph^FF-CF₃ Preferred specific examples of the compound wherein Z = CF ₃ include the following compounds. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-CF ₃ H-Ph-CH (CH ₃ )- CH ₂ -Ph-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-Ph ^FF -CF ₃ H-Ph-CHF-CH ₂ -Ph-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph ^F -CF ₃ H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CF ₃ H-Ph-CHF-CH ₂ -Ph -COO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-COO-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-COO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph-CF ₃ H-Ph-CH ( CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -CF ₃ H -Ph-CHF-CH ₂ -Ph-OCO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-OCO-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CO- Ph-OCO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F- _{_{_{CH 2 CH 2 -Ph-CF 3}}} H-Ph-CH (CH 3) -CH 2 -Ph-CH 2 CH 2 -Ph FF -CF 3 H-Ph-CH (CH 3) -CH 2 -Ph FF - CH ₂ CH ₂ -Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH _2- Ph ^FF -CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CHF-CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph ^F -CF ₃ H-Ph-CH (CH ₃ )- CH ₂ -Ph ^F -CH ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph ^F -CF ₃ H-Ph-CH (CH ₃ )- CH ₂ -Ph ^FF -CH ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^FF -CF ₃ H-Ph-CHF-CH ₂ -Ph- CH ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-CH ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-CH ₂ O- Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph-CF ₃ H-Ph -CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^FF -CF ₃ H-Ph-CHF-CH ₂ -Ph-OCH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph- CF = CF-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF = CF-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CF = CF- Ph ^FF -CF ₃ H-Ph-CHF-CH ₂ -Ph-CF = CF-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-CF = CF-Ph ^FF -CF ₃ H- Ph-CH (CF ₃ ) -CO-Ph-CF = CF-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph-CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -CF ₃ H-Ph-CHF-CH _2- Ph-CF ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-CF ₂ O-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-CF ₂ O-Ph ^FF -CF ₃

【００１９】Ｚ＝ＯＣＦ₃である化合物の好ましい具体
例は、下記化合物が挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CH₂-Ph-Ph^FF-OCF₃ H-Ph-CHF-CH₂-Ph-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CO-Ph-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CO-Ph-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CH₂-Ph-COO-Ph^FF-OCF₃ H-Ph-CHF-CH₂-Ph-COO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CO-Ph-COO-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CO-Ph-COO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CH₂-Ph-OCO-Ph^FF-OCF₃ H-Ph-CHF-CH₂-Ph-OCO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CO-Ph-OCO-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CO-Ph-OCO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CH₂-Ph-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CHF-CH₂-Ph-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CO-Ph-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CO-Ph-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CH₂-Ph-CH₂O-Ph^FF-OCF₃ H-Ph-CHF-CH₂-Ph-CH₂O-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CO-Ph-CH₂O-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CO-Ph-CH₂O-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CH₂-Ph-OCH₂-Ph^FF-OCF₃ H-Ph-CHF-CH₂-Ph-OCH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CO-Ph-OCH₂-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CO-Ph-OCH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CH₂-Ph-CF=CF-Ph^FF-OCF₃ H-Ph-CHF-CH₂-Ph-CF=CF-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CO-Ph-CF=CF-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CO-Ph-CF=CF-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CH₂-Ph-CF₂O-Ph^FF-OCF₃H-Ph-CHF-CH₂-Ph-
CF₂O-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CO-Ph-CF₂O-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CO-Ph-CF₂O-Ph^FF-OCF₃ Preferred specific examples of the compound wherein Z = OCF ₃ include the following compounds. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-OCF ₃ H-Ph-CH (CH ₃ )- CH ₂ -Ph-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-Ph ^FF -OCF ₃ H-Ph-CHF-CH ₂ -Ph-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph ^F -OCF ₃ H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-COO-Ph ^FF -OCF ₃ H-Ph-CHF-CH ₂ -Ph -COO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-COO-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-COO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -O CO-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^FF -OCF ₃ H-Ph- CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -OCF ₃ H-Ph-CHF-CH ₂ -Ph-OCO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-OCO-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-OCO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^F -OCF ₃ H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -OCF ₃ H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph ^F- OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CHF-CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -OCF ₃ H- Ph-CH (CF ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph -CH (CH ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^FF -OCF ₃ H-Ph-CHF-CH ₂ -Ph-CH ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CO-Ph -CH ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-CH ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCH ₂ ^{_{-Ph F -OCF 3 H-Ph-}} CH (CH 3) -CH 2 -Ph F -OCH 2 -Ph-OCF 3 H-Ph-CH (CH 3) -CH 2 -Ph-OCH 2 -Ph FF - OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^F -OCF ₃ H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^F -OCF ₃ H-Ph -CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^FF -OCF ₃ H-Ph-CHF- CH ₂ -Ph-OCH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF = CF-Ph ^F -OCF ₃ H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF = CF-Ph ^FF -OCF ₃ H-Ph -CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph ^F -OCF ₃ H-Ph- CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph ^F -OCF ₃ H-Ph- CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CF = CF-Ph ^FF -OCF ₃ H-Ph-CHF -CH ₂ -Ph-CF = CF-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-CF = CF-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CO- Ph-CF = CF-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph-OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -OCF ₃ H-Ph-CHF-CH ₂ -Ph-
CF ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CO-Ph-CF ₂ O-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CO-Ph-CF ₂ O- Ph ^FF -OCF ₃

【００２０】Ｚ＝ＳＦ₅である化合物の好ましい具体例
は、下記化合物が挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^FF-SF₅ H-Ph-CH(CF₃)-CH₂-Ph-Ph^FF-SF₅ H-Ph-CHF-CH₂-Ph-Ph^FF-SF₅ H-Ph-CH(CH₃)-CO-Ph-Ph^FF-SF₅ H-Ph-CH(CF₃)-CO-Ph-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^FF-SF₅ H-Ph-CH(CF₃)-CH₂-Ph-COO-Ph^FF-SF₅ H-Ph-CHF-CH₂-Ph-COO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CO-Ph-COO-Ph^FF-SF₅ H-Ph-CH(CF₃)-CO-Ph-COO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^FF-SF₅ H-Ph-CH(CF₃)-CH₂-Ph-OCO-Ph^FF-SF₅ H-Ph-CHF-CH₂-Ph-OCO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CO-Ph-OCO-Ph^FF-SF₅ H-Ph-CH(CF₃)-CO-Ph-OCO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CF₃)-CH₂-Ph-CH₂CH₂-Ph^FF-SF₅ H-Ph-CHF-CH₂-Ph-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CO-Ph-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CF₃)-CO-Ph-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph^F-SF₅H-Ph-CH(CH₃)-CH₂-
Ph^F-CH₂O-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^FF-SF₅ H-Ph-CH(CF₃)-CH₂-Ph-CH₂O-Ph^FF-SF₅ H-Ph-CHF-CH₂-Ph-CH₂O-Ph^FF-SF₅ H-Ph-CH(CH₃)-CO-Ph-CH₂O-Ph^FF-SF₅ H-Ph-CH(CF₃)-CO-Ph-CH₂O-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^FF-SF₅ H-Ph-CH(CF₃)-CH₂-Ph-OCH₂-Ph^FF-SF₅ H-Ph-CHF-CH₂-Ph-OCH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CO-Ph-OCH₂-Ph^FF-SF₅ H-Ph-CH(CF₃)-CO-Ph-OCH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^FF-SF₅ H-Ph-CH(CF₃)-CH₂-Ph-CF=CF-Ph^FF-SF₅ H-Ph-CHF-CH₂-Ph-CF=CF-Ph^FF-SF₅ H-Ph-CH(CH₃)-CO-Ph-CF=CF-Ph^FF-SF₅ H-Ph-CH(CF₃)-CO-Ph-CF=CF-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^FF-SF₅ H-Ph-CH(CF₃)-CH₂-Ph-CF₂O-Ph^FF-SF₅ H-Ph-CHF-CH₂-Ph-CF₂O-Ph^FF-SF₅ H-Ph-CH(CH₃)-CO-Ph-CF₂O-Ph^FF-SF₅ H-Ph-CH(CF₃)-CO-Ph-CF₂O-Ph^FF-SF₅ Preferred specific examples of the compound in which Z = SF ₅ include the following compounds. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-SF ₅ H-Ph-CH (CH ₃ )- CH ₂ -Ph-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-Ph ^FF -SF ₅ H-Ph-CHF-CH ₂ -Ph-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CO-Ph-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CO-Ph-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph ^F -SF ₅ H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-COO-Ph ^FF -SF ₅ H-Ph-CHF-CH ₂ -Ph -COO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CO-Ph-COO-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CO-Ph-COO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph-SF ₅ H-Ph-CH ( CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -SF ₅ H -Ph-CHF-CH ₂ -Ph-OCO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CO-Ph-OCO-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CO- Ph-OCO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F- _{_{_{CH 2 CH 2 -Ph-SF 5}}} H-Ph-CH (CH 3) -CH 2 -Ph-CH 2 CH 2 -Ph FF -SF 5 H-Ph-CH (CH 3) -CH 2 -Ph FF - CH ₂ CH ₂ -Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH _2- Ph ^FF -CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CHF-CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^F -SF ₅ H-Ph-CH (CH _{_{^{_{3) -CH 2 -Ph F -CH 2}}}} O-Ph-SF 5 H-Ph-CH (CH 3) -CH 2 -Ph-CH 2 O-Ph FF -SF 5 H-Ph-CH (CH 3) -CH ₂ -Ph ^FF -CH ₂ O-Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph ^F -SF ₅ H-Ph-CH (CH ₃ )- CH _2-
Ph ^F -CH ₂ O-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH _2- Ph ^FF -CH ₂ O-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^FF -SF ₅ H-Ph-CHF-CH ₂ -Ph-CH ₂ O -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CO-Ph-CH ₂ O-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CO-Ph-CH ₂ O-Ph ^FF- SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph-SF ₅ H- Ph-CH (CH ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph-SF ₅ H-Ph-CH ( CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CF ₃ )- CH ₂ -Ph-OCH ₂ -Ph ^FF -SF ₅ H-Ph-CHF-CH ₂ -Ph-OCH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF = CF-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF = CF-Ph ^FF -SF ₅ H- Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CF = CF-Ph ^FF -SF ₅ H-Ph-CHF-CH ₂ -Ph-CF = CF-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CO-Ph-CF = CF-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CO-Ph-CF = CF-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^F -SF ₅ H-Ph-CH (CH ₃ )- CH ₂ -Ph ^F -CF ₂ O-Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph-SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH _2- Ph ^F -CF ₂ O-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH _2- Ph ^FF -CF ₂ O-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -SF ₅ H-Ph-CHF-CH ₂ -Ph-CF ₂ O -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CO-Ph-CF ₂ O-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CO-Ph-CF ₂ O-Ph ^FF- SF ₅

【００２１】Ｚ＝Ｆである化合物の好ましく具体例は、
下記化合物が挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-F H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph-F H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^FF-F H-Ph-CH(CF₃)-CH₂-Ph-Ph^FF-F H-Ph-CHF-CH₂-Ph-Ph^FF-F H-Ph-CH(CH₃)-CO-Ph-Ph^FF-F H-Ph-CH(CF₃)-CO-Ph-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph-F H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph-F H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-COO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Ph^FF-F H-Ph-CH(CF₃)-CH₂-Ph-COO-Ph^FF-F H-Ph-CHF-CH₂-Ph-COO-Ph^FF-F H-Ph-CH(CH₃)-CO-Ph-COO-Ph^FF-F H-Ph-CH(CF₃)-CO-Ph-COO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph-F H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph-F H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-OCO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Ph^FF-F H-Ph-CH(CF₃)-CH₂-Ph-OCO-Ph^FF-F H-Ph-CHF-CH₂-Ph-OCO-Ph^FF-F H-Ph-CH(CH₃)-CO-Ph-OCO-Ph^FF-F H-Ph-CH(CF₃)-CO-Ph-OCO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph-F H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph-F H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂CH₂-Ph^FF-F₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Ph^FF-F H-Ph-CH(CF₃)-CH₂-Ph-CH₂CH₂-Ph^FF-F H-Ph-CHF-CH₂-Ph-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CO-Ph-CH₂CH₂-Ph^FF-F H-Ph-CH(CF₃)-CO-Ph-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph-F H-Ph-CH(CH₃)-CH₂-Ph-CH₂O-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph-F H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-CH₂O-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂O-Ph^FF-F H-Ph-CH(CF₃)-CH₂-Ph-CH₂O-Ph^FF-F H-Ph-CHF-CH₂-Ph-CH₂O-Ph^FF-F H-Ph-CH(CH₃)-CO-Ph-CH₂O-Ph^FF-F H-Ph-CH(CF₃)-CO-Ph-CH₂O-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph-F H-Ph-CH(CH₃)-CH₂-Ph-OCH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph-F H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-OCH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-OCH₂-Ph^FF-F H-Ph-CH(CF₃)-CH₂-Ph-OCH₂-Ph^FF-F H-Ph-CHF-CH₂-Ph-OCH₂-Ph^FF-F H-Ph-CH(CH₃)-CO-Ph-OCH₂-Ph^FF-F H-Ph-CH(CF₃)-CO-Ph-OCH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph-F H-Ph-CH(CH₃)-CH₂-Ph-CF=CF-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph-F H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-CF=CF-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^FF-F H-Ph-CH(CF₃)-CH₂-Ph-CF=CF-Ph^FF-F H-Ph-CHF-CH₂-Ph-CF=CF-Ph^FF-F H-Ph-CH(CH₃)-CO-Ph-CF=CF-Ph^FF-F H-Ph-CH(CF₃)-CO-Ph-CF=CF-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph-F H-Ph-CH(CH₃)-CH₂-Ph-CF₂O-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph-F H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^F-CF₂O-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CF₂O-Ph^FF-F H-Ph-CH(CF₃)-CH₂-Ph-CF₂O-Ph^FF-F H-Ph-CHF-CH₂-Ph-CF₂O-Ph^FF-F H-Ph-CH(CH₃)-CO-Ph-CF₂O-Ph^FF-F H-Ph-CH(CF₃)-CO-Ph-CF₂O-Ph^FF-FPreferred specific examples of the compound wherein Z = F are:
The following compounds are mentioned. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^F -F H-Ph- CH (CH ₃ ) -CH ₂ -Ph ^F -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Ph ^FF -F H-Ph-CH (CF ₃ ) -CH ₂ -Ph-Ph ^FF -F H-Ph-CHF-CH ₂ -Ph-Ph ^FF -F H-Ph-CH (CH ₃ )- CO-Ph-Ph ^FF -F H-Ph-CH (CF ₃ ) -CO-Ph-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^F -F H-Ph -CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -COO- Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Ph ^FF -F H- Ph-CH (CF ₃ ) -CH ₂ -Ph-COO-Ph ^FF -F H-Ph-CHF-CH ₂ -Ph-COO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CO-Ph- COO-Ph ^FF -F H-Ph-CH (CF ₃ ) -CO-Ph-COO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^F -F H-Ph -CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Ph ^FF -F H-Ph-CH (CF ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -F H- Ph-CHF-CH ₂ -Ph-OCO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CO-Ph-OCO-Ph ^FF -F H-Ph-CH (CF ₃ ) -CO-Ph-OCO -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ CH _2- Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph- F H-Ph-CH (CH 3) -CH 2 -Ph F -CH 2 CH 2 -Ph F -F H-Ph-CH (CH 3) -CH 2 -Ph F -CH 2 CH 2 -Ph FF - F ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Ph ^FF -F H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -F H-Ph-CHF-CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -F H-Ph- CH (CH ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -F H-Ph-CH (CF ₃ ) -CO-Ph-CH ₂ CH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F- CH ₂ O-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CH ₂ O-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph ^F- F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ O-Ph ^FF -F H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CH ₂ O-Ph ^FF -F H- Ph-CHF-CH ₂ -Ph-CH ₂ O-Ph ^FF -F H-Ph-CH (CH ₃ ) -CO-Ph-CH ₂ O-Ph ^FF -F H-Ph-CH (CF ₃ ) -CO -Ph-CH ₂ O-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph-F H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -OCH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCH ₂ -Ph ^FF -F H-Ph-CH (CF ₃ ) -CH ₂ -Ph-OCH ₂ -Ph ^FF -F H-Ph-CHF-CH ₂ -Ph-OCH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -F H-Ph-CH (CF ₃ ) -CO-Ph-OCH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF = CF-Ph ^F -F H-Ph- CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF = CF-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF = CF-Ph ^FF -F H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF = CF-Ph ^FF -F H-Ph -CH (CF ₃ ) -CH ₂ -Ph-CF = CF-Ph ^FF -F H-Ph-CHF-CH ₂ -Ph-CF = CF-Ph ^FF -F H-Ph-CH (CH ₃ ) -CO -Ph-CF = CF-Ph ^FF -F H-Ph-CH (CF ₃ ) -CO-Ph-CF = CF-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph-F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph ^F -F H -Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -CF ₂ O-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph ^F -F H-Ph -CH (CH ₃ ) -CH ₂ -Ph ^FF -CF ₂ O-Ph ^FF -F H-Ph-CH (CF ₃ ) -CH ₂ -Ph-CF ₂ O-Ph ^FF -F H-Ph-CHF- CH ₂ -Ph-CF ₂ O-Ph ^FF -F H-Ph-CH (CH ₃ ) -CO-Ph-CF ₂ O-Ph ^FF -F H-Ph-CH (CF ₃ ) -CO-Ph-CF ₂ O-Ph ^FF -F

【００２２】＜環基の数が４である化合物の具体例＞Ｚ
＝ＣＮである化合物の好ましい具体例は、下記化合物が
挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-Ph^FF-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-Cy-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-Cy-Ph^FF-CN H-Ph-CH(CF₃)-CH₂-Ph^FF-Ph-Ph^FF-CN H-Ph-CHF-CH₂-Ph^FF-Ph-Ph^FF-CN H-Ph-CH(CH₃)-CO-CH₂-Ph^FF-Ph-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-COO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-Cy-COO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-OCO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-Cy-OCO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-Cy-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-COO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-COO-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-COO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-COO-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-CH₂CH₂-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-CH₂CH₂-Ph^F-CN H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-CH₂CH₂-Ph^FF-CN H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-CH₂CH₂-Ph^FF-CN<Specific examples of the compound having 4 ring groups> Z
Preferred specific examples of the compound where = CN include the following compounds. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-Ph ^FF -CN H-Ph-CH ( CH ₃ ) -CH ₂ -Cy-Ph ^FF -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Cy-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-Ph ^FF -CN H-Ph-CH (CF ₃ ) -CH ₂ -Ph ^FF -Ph-Ph ^FF -CN H-Ph-CHF-CH ₂ -Ph ^FF -Ph-Ph ^FF -CN H -Ph-CH (CH ₃ ) -CO-CH ₂ -Ph ^FF -Ph-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -COO-Ph ^FF -CN H-Ph -CH (CH ₃ ) -CH ₂ -Cy-COO-Ph ^FF -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-COO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Cy-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -OCO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Cy-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-OCO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy -OCO-Cy-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy -CH ₂ CH ₂ -Ph ^FF -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-Ph ^FF -CN H-Ph-CH (CH ₃ )- CH ₂ -Cy-Cy-CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-Ph ^FF -C N H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -COO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH _2- Ph ^FF -COO-Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-COO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-COO-Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Ph ^FF -CH ₂ CH ₂ -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy-CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Cy-CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^F -CN H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Cy-CH ₂ CH ₂ -Ph ^FF -CN H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Cy-CH ₂ CH ₂ -Ph ^FF -CN

【００２３】Ｚ＝ＣＦ₃である化合物の好ましい具体例
は、下記化合物が挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-Ph^FF-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-Cy-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-Cy-Ph^FF-CF₃ H-Ph-CH(CF₃)-CH₂-Ph^FF-Ph-Ph^FF-CF₃ H-Ph-CHF-CH₂-Ph^FF-Ph-Ph^FF-CF₃ H-Ph-CH(CH₃)-CO-CH₂-Ph^FF-Ph-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-COO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-Cy-COO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-OCO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-Cy-OCO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-Cy-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-COO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-COO-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-COO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-COO-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-CH₂CH₂-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-CH₂CH₂-Ph^F-CF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-CH₂CH₂-Ph^FF-CF₃ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-CH₂CH₂-Ph^FF-CF₃ Preferred specific examples of the compound wherein Z = CF ₃ include the following compounds. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-Ph ^FF -CF ₃ H-Ph- CH (CH ₃ ) -CH ₂ -Cy-Ph ^FF -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Cy-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-Ph ^FF -CF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph ^FF -Ph-Ph ^FF -CF ₃ H-Ph-CHF-CH ₂ -Ph ^FF -Ph -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CO-CH ₂ -Ph ^FF -Ph-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -COO -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Ph ^FF -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-COO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Cy-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -OCO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Cy-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-OCO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Cy-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -CH ₂ CH _2- Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Ph ^FF -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-CH ₂ CH ₂ -Ph ^FF -CF ₃ H- Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -COO- Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Ph ^FF -COO-Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-COO-Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-COO-Ph ^FF -CF ₃ H-Ph-CH ( CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Ph ^FF -CH ₂ CH ₂ -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy-CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO -Cy-CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^F -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Cy-CH ₂ CH ₂ -Ph ^FF -CF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Cy-CH ₂ CH ₂ -Ph ^FF -CF ₃

【００２４】Ｚ＝ＯＣＦ₃である化合物の好ましい具体
例は、下記化合物が挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-Ph^FF-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-Cy-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-Cy-Ph^FF-OCF₃ H-Ph-CH(CF₃)-CH₂-Ph^FF-Ph-Ph^FF-OCF₃ H-Ph-CHF-CH₂-Ph^FF-Ph-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CO-CH₂-Ph^FF-Ph-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-COO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-Cy-COO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-OCO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-Cy-OCO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-Cy-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-COO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-COO-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-COO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-COO-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-CH₂CH₂-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-CH₂CH₂-Ph^F-OCF₃ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-CH₂CH₂-Ph^FF-OCF₃ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-CH₂CH₂-Ph^FF-OCF₃ Preferred specific examples of the compound wherein Z = OCF ₃ include the following compounds. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-Ph ^FF -OCF ₃ H-Ph- CH (CH ₃ ) -CH ₂ -Cy-Ph ^FF -Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Cy-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-Ph ^FF -OCF ₃ H-Ph-CH (CF ₃ ) -CH ₂ -Ph ^FF -Ph-Ph ^FF -OCF ₃ H-Ph-CHF-CH ₂ -Ph ^FF -Ph -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CO-CH ₂ -Ph ^FF -Ph-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -COO -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Ph ^FF -Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-COO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Cy-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -OCO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Cy-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-OCO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Cy-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -CH ₂ CH _2- Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Ph ^FF -Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph- CH ₂ CH ₂ -Ph ^FF -COO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Ph ^FF -COO-Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-COO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-COO-Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO -Ph ^FF -CH ₂ CH ₂ -Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy-CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CH ( CH ₃ ) -CH ₂ -Cy-COO-Cy-CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^F -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO -Cy-CH ₂ CH ₂ -Ph ^FF -OCF ₃ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Cy-CH ₂ CH ₂ -Ph ^FF -OCF ₃

【００２５】Ｚ＝Ｆである化合物の好ましい具体例は、
下記化合物が挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-Ph^FF-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-Cy-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-Cy-Ph^FF-F H-Ph-CH(CF₃)-CH₂-Ph^FF-Ph-Ph^FF-F H-Ph-CHF-CH₂-Ph^FF-Ph-Ph^FF-F H-Ph-CH(CH₃)-CO-CH₂-Ph^FF-Ph-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-COO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-Cy-COO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-OCO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-Cy-OCO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-Cy-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-COO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-COO-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-COO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-COO-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-CH₂CH₂-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-CH₂CH₂-Ph^F-F H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-CH₂CH₂-Ph^FF-F H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-CH₂CH₂-Ph^FF-FA preferred embodiment of the compound wherein Z = F is
The following compounds are mentioned. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-Ph ^FF -F H-Ph-CH ( CH ₃ ) -CH ₂ -Cy-Ph ^FF -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Cy-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-Ph ^FF -F H-Ph-CH (CF ₃ ) -CH ₂ -Ph ^FF -Ph-Ph ^FF -F H-Ph-CHF-CH ₂ -Ph ^FF -Ph-Ph ^FF -F H -Ph-CH (CH ₃ ) -CO-CH ₂ -Ph ^FF -Ph-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -COO-Ph ^FF -F H-Ph -CH (CH ₃ ) -CH ₂ -Cy-COO-Ph ^FF -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-COO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Cy-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -OCO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Cy-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-OCO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy -OCO-Cy-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy -CH ₂ CH ₂ -Ph ^FF -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-Ph ^FF -F H-Ph-CH (CH ₃ )- CH ₂ -Cy-Cy-CH ₂ CH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH _2- Ph-CH ₂ CH ₂ -Ph ^FF -COO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Ph ^FF -COO-Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-COO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-COO-Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Ph ^FF -CH ₂ CH ₂ -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy-CH ₂ CH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Cy-CH ₂ CH ₂ -Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -F H-Ph- CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^F -F H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Cy-CH ₂ CH _2- Ph ^FF -F H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Cy-CH ₂ CH ₂ -Ph ^FF -F

【００２６】Ｚ＝ＳＦ₅である化合物の好ましい具体例
は、下記化合物が挙げられる。 H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^F-Ph-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-Ph^FF-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-Cy-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-Cy-Ph^FF-SF₅ H-Ph-CH(CF₃)-CH₂-Ph^FF-Ph-Ph^FF-SF₅ H-Ph-CHF-CH₂-Ph^FF-Ph-Ph^FF-SF₅ H-Ph-CH(CH₃)-CO-CH₂-Ph^FF-Ph-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-COO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-Cy-COO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-OCO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-Cy-OCO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-Cy-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-CH₂CH₂-Ph^FF-COO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Ph^FF-COO-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-CH₂CH₂-Cy-COO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-CH₂CH₂-Cy-COO-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-COO-Ph^FF-CH₂CH₂-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-COO-Cy-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-COO-Cy-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Ph-OCO-Ph^FF-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Ph^FF-CH₂CH₂-Ph^F-SF₅ H-Ph-CH(CH₃)-CH₂-Ph^FF-OCO-Cy-CH₂CH₂-Ph^FF-SF₅ H-Ph-CH(CH₃)-CH₂-Cy-OCO-Cy-CH₂CH₂-Ph^FF-SF₅ Preferred specific examples of the compound wherein Z = SF ₅ include the following compounds. H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^F -Ph-Ph ^FF -SF ₅ H-Ph- CH (CH ₃ ) -CH ₂ -Cy-Ph ^FF -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -Cy-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-Ph ^FF -SF ₅ H-Ph-CH (CF ₃ ) -CH ₂ -Ph ^FF -Ph-Ph ^FF -SF ₅ H-Ph-CHF-CH ₂ -Ph ^FF -Ph -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CO-CH ₂ -Ph ^FF -Ph-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -COO -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Ph ^FF -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-COO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Cy-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -OCO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Cy-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-OCO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Cy-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -CH ₂ CH _2- Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Ph ^FF -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-Cy-CH ₂ CH ₂ -Ph ^FF -SF ₅ H- Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-CH ₂ CH ₂ -Ph ^FF -COO- Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Ph ^FF -COO-Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -CH ₂ CH ₂ -Cy-COO-Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-CH ₂ CH ₂ -Cy-COO-Ph ^FF -SF ₅ H-Ph-CH ( CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO-Ph ^FF -CH ₂ CH ₂ -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -COO-Cy-CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-COO -Cy-CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Ph ^FF -CH ₂ CH ₂ -Ph ^F -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Ph ^FF -OCO-Cy-CH ₂ CH ₂ -Ph ^FF -SF ₅ H-Ph-CH (CH ₃ ) -CH ₂ -Cy-OCO-Cy-CH ₂ CH ₂ -Ph ^FF -SF ₅

【００２７】［製造方法の説明］本発明における光学活
性化合物（１）は新規化合物であり、たとえば次の方法
に従って製造されうる。なお、下記の製造方法は好まし
い例示であり、必要に応じて他の種々の製造方法が使用
できる。なお、以下において、−Ｐｈ’−は式（７）、
−Ｐｈ’’−は式（８））を示す。[Description of Production Method] The optically active compound (1) in the present invention is a novel compound and can be produced, for example, according to the following method. The following production method is a preferred example, and other various production methods can be used as needed. In the following, -Ph'- is represented by the formula (7),
-Ph "-represents the equation (8).

【化８】 Embedded image

【００２８】［方法１］ＡがＣＨ₂であり、Ｂ₁、Ｂ₂、
Ｄ₁、Ｄ₂が単結合であり、Ｂ₃が−ＣＯＯ−である場
合。 H-Ph-CHX-COOH 式ａ１ ↓ SOCl₂ H-Ph-CHX-COCl 式ｂ１ ↓ Fe(acac)₃、BrMg-Ph'-Cl 式ｃ１ H-Ph-CHX-CO-Ph'-Cl 式ｄ１ ↓ Et₃SiH、CF₃COOH H-Ph-CHX-CH₂-Ph'-Cl 式ｅ１ ↓ EtMgBr、Mg ↓ CO₂、H⁺ H-Ph-CHX-CH₂-Ph'-COOH 式ｆ１ ↓ SOCl₂ H-Ph-CHX-CH₂-Ph'-COCl 式ｇ１ ↓ ピリジン、HO-Ph''-Z 式ｈ１ H-Ph-CHX-CH₂-Ph'-COO-Ph''-Z 式ｉ１[Method 1] A is CH ₂ , B ₁ , B ₂ ,
When D ₁ and D ₂ are a single bond, and B ₃ is —COO—. H-Ph-CHX-COOH Formula a1 ↓ SOCl ₂ H-Ph-CHX-COCl Formula b1 ↓ Fe (acac) ₃ , BrMg-Ph'-Cl Formula c1 H-Ph-CHX-CO-Ph'-Cl Formula d1 ↓ Et ₃ SiH, CF ₃ COOH H-Ph-CHX-CH ₂ -Ph'-Cl Formula e1 ↓ EtMgBr, Mg ↓ CO ₂ , H ⁺ H-Ph-CHX-CH ₂ -Ph'-COOH Formula f1 ↓ SOCl _{2 H-Ph-CHX-CH} 2 -Ph'-COCl formula g1 ↓ pyridine, HO-Ph '' - Z formula h1 H-Ph-CHX-CH 2 -Ph'-COO-Ph '' - Z formula i1

【００２９】光学活性カルボン酸（式ａ１）を塩化チオ
ニル等にて酸クロリド化して酸クロリド（式ｂ１）を得
て、さらに鉄（III）アセチルアセトナート［Ｆｅ（ａ
ｃａｃ）₃］等の有機金属触媒存在下、グリニヤール試
薬（式ｃ１）と反応させることによりケトン（式ｄ１）
を得る。ケトン（式ｄ１）をトリフルオロ酢酸存在下の
トリエチルシラン等の還元剤によって還元することによ
り化合物（式ｅ１）を得る。化合物（式ｅ１）をエチル
マグネシウムブロミド存在下マグネシウムによりグリニ
ヤール試薬とし、二酸化炭素と反応させた後に酸により
加水分解してカルボン酸（式ｆ１）を得て、塩化チオニ
ル等にて酸クロリド化して酸クロリド（式ｇ１）を得
て、さらにピリジン等の存在下、化合物（式ｈ１）との
反応により目的の光学活性化合物（式ｉ１）を得る。The optically active carboxylic acid (formula a1) is acid chlorided with thionyl chloride or the like to obtain an acid chloride (formula b1), and further, iron (III) acetylacetonate [Fe (a
cac) ₃ ] and a ketone (formula d1) by reacting with a Grignard reagent (formula c1) in the presence of an organometallic catalyst such as
Get. The compound (formula e1) is obtained by reducing the ketone (formula d1) with a reducing agent such as triethylsilane in the presence of trifluoroacetic acid. The compound (formula e1) is converted to a Grignard reagent with magnesium in the presence of ethylmagnesium bromide, reacted with carbon dioxide, and then hydrolyzed with an acid to obtain a carboxylic acid (formula f1). Chloride (formula g1) is obtained, and the desired optically active compound (formula i1) is obtained by reaction with a compound (formula h1) in the presence of pyridine and the like.

【００３０】［方法２］ＡがＣＨ₂であり、Ｂ₁、Ｂ₂、
Ｂ₃、Ｄ₁、Ｄ₂が単結合であり、Ｚが−ＣＮである場
合。 H-Ph-CHX-CH₂-Ph'-Cl 式ｅ１ ↓ EtMgBr、Mg ↓ B(OCH₃)₃、H⁺ H-Ph-CHX-CH₂-Ph'-B(OH)₂ 式ａ２ ↓ Pd(PPh3)4、Br-Ph''-H 式ｂ２ H-Ph-CHX-CH₂-Ph'-Ph''-H 式ｃ２ ↓ BuLi ↓ CO₂、H⁺ H-Ph-CHX-CH₂-Ph'-Ph''-COOH 式ｄ２ ↓ SOCl₂ H-Ph-CHX-CH₂-Ph'-Ph''-COCl 式ｅ２ ↓ NH₄OH H-Ph-CHX-CH₂-Ph'-Ph''-CONH₂ 式ｆ２ ↓ ピリジン、TsCl H-Ph-CHX-CH₂-Ph'-Ph''-CN 式ｇ２[Method 2] A is CH ₂ and B ₁ , B ₂ ,
B ₃ , D ₁ , and D ₂ are a single bond, and Z is —CN. H-Ph-CHX-CH ₂ -Ph'-Cl Formula e1 ↓ EtMgBr, Mg ↓ B (OCH ₃ ) ₃ , H ⁺ H-Ph-CHX-CH ₂ -Ph'-B (OH) ₂ Formula a2 ↓ Pd (PPh3) 4, Br-Ph '' - H type b2 H-Ph-CHX-CH 2 -Ph'-Ph '' - H type _{c2 ↓ BuLi ↓ CO 2, H} + H-Ph-CHX-CH 2 - Ph'-Ph ''-COOH formula d2 ↓ SOCl ₂ H-Ph-CHX-CH ₂ -Ph'-Ph ''-COCl formula e2 ↓ NH ₄ OH H-Ph-CHX-CH ₂ -Ph'-Ph ''-CONH ₂ formula f2 ↓ Pyridine, TsCl H-Ph-CHX-CH ₂ -Ph'-Ph''-CN formula g2

【００３１】化合物（式ｅ１）をエチルマグネシウムブ
ロミド存在下マグネシウムによりグリニヤール試薬と
し、ホウ酸トリメチルと反応させた後に酸により加水分
解して化合物（式ａ２）を得て、Ｐｄ（ＰＰｈ₃）₄等の
有機金属触媒存在下化合物（式ｂ２）との反応により化
合物（式ｃ２）を得る。化合物（式ｃ２）をブチルリチ
ウムによりリチオ化し、二酸化炭素と反応させた後に酸
により加水分解してカルボン酸（式ｄ２）を得る。カル
ボン酸（式ｄ２）を塩化チオニル等にて酸クロリド化し
て酸クロリド（式ｅ２）を得て、アンモニア水と反応さ
せてアミド（式ｆ２）を得て、さらにピリジン等の存在
下ｐ−トルエンスルホン酸クロリド等による脱水反応に
より目的の光学活性化合物（式ｇ２）を得る。The compound (formula e1) is converted into a Grignard reagent with magnesium in the presence of ethylmagnesium bromide, reacted with trimethyl borate, and then hydrolyzed with an acid to obtain a compound (formula a2), Pd (PPh ₃ ) _{4 and the} like. Reaction with a compound (formula b2) in the presence of an organometallic catalyst to give a compound (formula c2). The compound (formula c2) is lithiated with butyllithium, reacted with carbon dioxide, and then hydrolyzed with an acid to obtain a carboxylic acid (formula d2). The carboxylic acid (formula d2) is acid chlorided with thionyl chloride or the like to obtain an acid chloride (formula e2), which is reacted with aqueous ammonia to give an amide (formula f2), and further p-toluene in the presence of pyridine or the like. The desired optically active compound (formula g2) is obtained by a dehydration reaction with sulfonic acid chloride or the like.

【００３２】［方法３］Ａが−ＣＨ₂−であり、Ｂ₁、Ｂ
₂、Ｄ₁、Ｄ₂が単結合であり、Ｂ₃が-ＯＣＯ−である場
合。 H-Ph-CHX-COOH 式ａ１ ↓ SOCl₂ H-Ph-CHX-COCl 式ｂ１ ↓ AlCl₃、H-Ph'-OCH₃ 式ａ３ H-Ph-CHX-CO-Ph'-OCH₃ 式ｂ３ ↓ AlCl₃、LiAlH₄ H-Ph-CHX-CH₂-Ph'-OCH₃ 式ｃ３ ↓ HBr、CH₃COOH H-Ph-CHX-CH₂-Ph'-OH 式ｄ３ ↓ ピリジン、ClOC-Ph''-Z 式ｅ３ H-Ph-CHX-CH₂-Ph'-OCO-Ph''-Z 式ｆ３[Method 3] A is —CH ₂ —, and B ₁ , B
₂ , D ₁ and D ₂ are a single bond, and B ₃ is —OCO—. H-Ph-CHX-COOH formula a1 ↓ SOCl ₂ H-Ph-CHX-COCl formula b1 ↓ AlCl ₃ , H-Ph'-OCH ₃ formula a3 H-Ph-CHX-CO-Ph'-OCH ₃ formula b3 ↓ AlCl ₃ , LiAlH ₄ H-Ph-CHX-CH ₂ -Ph'-OCH ₃ Formula c3 ↓ HBr, CH ₃ COOH H-Ph-CHX-CH ₂ -Ph'-OH Formula d3 ↓ Pyridine, ClOC-Ph '' -Z Formula e3 H-Ph-CHX-CH ₂ -Ph'-OCO-Ph "-Z Formula f3

【００３３】光学活性カルボン酸（式ａ１）を塩化チオ
ニル等にて酸クロリド化して酸クロリド（式ｂ１）を得
て、さらに塩化アルミニウム等のルイス酸の存在下、化
合物（式ａ３）とのフリーデル・クラフツ反応によりケ
トン（式ｂ３）を得る。ケトン（式ｂ３）を塩化アルミ
ニウム等のルイス酸の存在下水素化リチウムアルミニウ
ム等の還元剤によって還元することにより化合物（式ｃ
３）を得る。化合物（式ｃ３）を酢酸存在下の臭化水素
酸等で処理することにより化合物（式ｄ３）を得て、さ
らにピリジン等の存在下、酸クロリド（式ｅ３）との反
応により目的の光学活性化合物（式ｆ３）を得る。The optically active carboxylic acid (formula a1) is acid chlorided with thionyl chloride or the like to obtain an acid chloride (formula b1), and further free from the compound (formula a3) in the presence of a Lewis acid such as aluminum chloride. The ketone (formula b3) is obtained by a Del-Crafts reaction. Reduction of the ketone (formula b3) with a reducing agent such as lithium aluminum hydride in the presence of a Lewis acid such as aluminum chloride gives the compound (formula c)
Obtain 3). The compound (formula c3) is treated with hydrobromic acid or the like in the presence of acetic acid to give the compound (formula d3), and further, in the presence of pyridine or the like, the desired optical activity is obtained by reaction with an acid chloride (formula e3). The compound (Formula f3) is obtained.

【００３４】［方法４］ＡがＣＨ₂であり、Ｂ₁、Ｂ₂、
Ｄ₁、Ｄ₂が単結合であり、Ｂ₃が−ＣＦ＝ＣＦ−である
場合。 H-Ph-CHX-CH₂-Ph'-H 式ａ４ ↓ BuLi ↓ CF₂=CF-Ph''-Z 式ｂ４ H-Ph-CHX-CH₂-Ph'-CF=CF-Ph''-Z 式ｃ４化合物（式ａ４）をブチルリチウムによりリチオ化し、
化合物（式ｂ４）と反応させることより目的の光学活性
化合物（式ｃ４）を得る。[Method 4] A is CH ₂ , B ₁ , B ₂ ,
D ₁ and D ₂ are single bonds, and B ₃ is —CFＣＦCF—. H-Ph-CHX-CH ₂ -Ph'-H Formula a4 ↓ BuLi ↓ CF ₂ = CF-Ph ''-Z Formula b4 H-Ph-CHX-CH ₂ -Ph'-CF = CF-Ph ''- Z Formula c4 The compound (formula a4) is lithiated with butyllithium,
The desired optically active compound (formula c4) is obtained by reacting with the compound (formula b4).

【００３５】［方法５］Ａが−ＣＨ₂−であり、Ｂ₁、Ｂ
₂、Ｄ₁、Ｄ₂が単結合であり、Ｂ₃が−ＣＦ₂Ｏ−である
場合。 H-Ph-CHX-CH₂-Ph'-H 式ａ４ ↓ BuLi ↓ CF₂Br₂ H-Ph-CHX-CH₂-Ph'-CF₂Br 式ａ５ ↓ K₂CO₃、HO-Ph''-Z 式ｂ５ H-Ph-CHX-CH₂-Ph'-CF₂O-Ph''-Z 式ｃ５化合物（式ａ４）をブチルリチウムによりリチオ化し、
ジブロモジフロロメタンと反応させ化合物（式ａ５）を
得て、炭酸カリウム等の存在下化合物（式ｂ５）と反応
させることより目的の光学活性化合物（式ｃ５）を得
る。[Method 5] A is —CH ₂ —, and B ₁ , B
₂ , D ₁ and D ₂ are a single bond, and B ₃ is —CF ₂ O—. H-Ph-CHX-CH ₂ -Ph'-H Formula a4 ↓ BuLi ↓ CF ₂ Br ₂ H-Ph-CHX-CH ₂ -Ph'-CF ₂ Br Formula a5 ↓ K ₂ CO ₃ , HO-Ph '' -Z Formula b5 H-Ph-CHX-CH ₂ -Ph′-CF ₂ O-Ph ″ -Z Formula c5 Compound (formula a4) is lithiated with butyllithium,
The desired optically active compound (formula c5) is obtained by reacting with dibromodifluoromethane to obtain a compound (formula a5) and reacting with a compound (formula b5) in the presence of potassium carbonate or the like.

【００３６】上記の方法は、それぞれの反応において、
式中の光学活性化合物の光学純度は保持される。いずれ
も該原料の絶対配置を保持しうる方法であるため、目的
とする光学活性化合物（１）の絶対配置により、適宜原
料化合物を変更すればよい。The above method involves the following in each reaction:
The optical purity of the optically active compound in the formula is maintained. In any case, since the absolute configuration of the raw material can be maintained, the raw material compound may be appropriately changed according to the absolute configuration of the target optically active compound (1).

【００３７】本発明の光学活性化合物（１）は、その１
種または２種以上を他の液晶材料および／または非液晶
材料（以下、他の液晶材料と非液晶材料とを総称して
「他の材料」という。）に含有させて液晶組成物とする
のが好ましい。The optically active compound (1) of the present invention comprises
A liquid crystal composition is formed by including one or more kinds in another liquid crystal material and / or a non-liquid crystal material (hereinafter, the other liquid crystal material and the non-liquid crystal material are collectively referred to as “other materials”). Is preferred.

【００３８】他の材料中に光学活性化合物（１）を含有
させて液晶組成物とする場合には、光学活性化合物
（１）を多成分含ませることが好ましく、その場合、一
成分の光学活性化合物（１）は、他の材料１００質量部
に対して、０．１〜１０質量部が好ましく、また、複数
の光学活性化合物（１）を含有させた場合のその合計量
は、他の材料１００質量部に対して０．１〜５０重量部
が好ましい。When the optically active compound (1) is contained in another material to form a liquid crystal composition, it is preferable that the optically active compound (1) is contained in multiple components. The compound (1) is preferably used in an amount of 0.1 to 10 parts by mass with respect to 100 parts by mass of the other material. 0.1 to 50 parts by weight per 100 parts by weight is preferred.

【００３９】他の材料としては、好ましくは、以下の化
合物が例示できる。なお、下式におけるＲ^A、Ｒ^Bはそれ
ぞれ相互に独立して、アルキル基、アルコキシ基、ハロ
ゲン原子、またはシアノ基を示し、Ｃｙはトランス−
１，４−ヘキシレン基、Ｐｈ^Aは非置換または置換され
た１，４−フェニレン基を示す。 R^A-Cy-Cy-R^B R^A-Cy-Ph^A-R^B R^A-Ph^A-Ph^A-R^B R^A-Cy-COO-Ph^A-R^B R^A-Ph^A-COO-Ph^A-R^B R^A-Ph^A-C≡C-Ph^A-R^B R^A-Cy-CH₂CH₂-Ph^A-C≡C-Ph^A-R^B R^A-Cy-CH₂CH₂-Ph^A-R^B R^A-Ph^A-CH₂CH₂-Ph^A-R^B R^A-Cy-Cy-Ph^A-R^B R^A-Cy-Ph^A-Ph^A-R^B R^A-Cy-Ph^A-Ph^A-Cy-R^B R^A-Ph^A-Ph^A-Ph^A-R^B R^A-Cy-COO-Ph^A-Ph^A-R^B R^A-Cy-Ph^A-COO-Ph^A-R^B R^A-Cy-COO-Ph^A-COO-Ph^A-R^B R^A-Ph^A-COO-Ph^A-COO-Ph^A-R^B R^A-Ph^A-COO-Ph^A-OCO-Ph^A-R^B As other materials, preferably, the following compounds can be exemplified. Note, R ^A in the formula, R ^B are each, independently of one another, an alkyl group, an alkoxy group, a halogen atom or a cyano group,, Cy is trans -
The 1,4-hexylene group and Ph ^A represent an unsubstituted or substituted 1,4-phenylene group. R ^A -Cy-Cy-R ^B R ^A -Cy-Ph ^A -R ^B R ^A -Ph ^A -Ph ^A -R ^B R ^A -Cy-COO-Ph ^A -R ^B R ^A -Ph ^A -COO- Ph ^A -R ^B R ^A -Ph ^A -C≡C-Ph ^A -R ^B R ^A -Cy-CH ₂ CH ₂ -Ph ^A -C≡C-Ph ^A -R ^B R ^A -Cy-CH ₂ CH ₂ -Ph ^A -R ^B R ^A -Ph ^A -CH ₂ CH ₂ -Ph ^A -R ^B R ^A -Cy-Cy-Ph ^A -R ^B R ^A -Cy-Ph ^A -Ph ^A -R ^B R ^A -Cy-Ph ^A -Ph ^A -Cy-R ^B R ^A -Ph ^A -Ph ^A -Ph ^A -R ^B R ^A -Cy-COO-Ph ^A -Ph ^A -R ^B R ^A -Cy-Ph ^A- COO-Ph ^A -R ^B R ^A -Cy-COO-Ph ^A -COO-Ph ^A -R ^B R ^A -Ph ^A -COO-Ph ^A -COO-Ph ^A -R ^B R ^A -Ph ^A -COO- Ph ^A -OCO-Ph ^A -R ^B

【００４０】上記化合物は、他の材料としての好ましい
例示であり、上記した化合物の環構造を、シクロヘキサ
ン環またはベンゼン環等の他の六員環、ピリジン環また
はジオキサン環等の他の複素環に置換してもよく、ま
た、化合物の末端水素原子をハロゲン原子、シアノ基、
メチル基等に置換してもよく、また、環と環の間の結合
基を他の結合基に変更してもよい。これらは所望の性能
に合わせて適宜変更されうる。The above compound is a preferred example as another material, and the ring structure of the above compound is changed to another 6-membered ring such as a cyclohexane ring or a benzene ring, or another heterocyclic ring such as a pyridine ring or a dioxane ring. May be substituted, and the terminal hydrogen atom of the compound is a halogen atom, a cyano group,
It may be substituted with a methyl group or the like, or the bonding group between rings may be changed to another bonding group. These can be appropriately changed according to desired performance.

【００４１】本発明の光学活性化合物（１）を含む液晶
組成物は、液晶セルに注入する等の方法により、電極付
の基板間に挟持して、液晶素子を構成する。液晶素子の
製造法としては、基本的には以下の方法が挙げられる。
すなわち、プラスチック、ガラス等の基板上に、必要に
応じてＳｉＯ₂、Ａｌ₂Ｏ₃等のアンダーコート層やカラ
ーフィルタ層を形成し、Ｉｎ₂Ｏ₃−ＳｎＯ₂（ＩＴ
Ｏ）、ＳｎＯ₂等の電極を設け、パターニングした後、
必要に応じてポリイミド、ポリアミド、ＳｉＯ₂、Ａｌ₂
Ｏ₃等のオーバーコート層を形成し、配向処理し、これ
にシール材を印刷し、電極面が相対向するように配して
周辺をシールし、シール材を硬化して空セルを形成す
る。The liquid crystal composition containing the optically active compound (1) of the present invention is sandwiched between substrates with electrodes by a method such as injection into a liquid crystal cell to constitute a liquid crystal element. Basically, the following method can be cited as a method for manufacturing a liquid crystal element.
That is, an undercoat layer such as SiO ₂ or Al ₂ O ₃ or a color filter layer is formed on a substrate such as plastic or glass, if necessary, to form an In ₂ O ₃ —SnO ₂ (IT
O), after providing electrodes such as SnO ₂ and patterning,
If necessary, polyimide, polyamide, SiO ₂ , Al ₂
An overcoat layer of O ₃ or the like is formed, orientation treatment is performed, a seal material is printed on the overcoat layer, and the periphery is sealed by disposing the electrode surfaces to face each other, and the seal material is cured to form empty cells. .

【００４２】この空セルに、本発明の光学活性化合物
（１）を含有する液晶組成物を注入し、注入口を封止剤
で封止して液晶セルを構成する。この液晶セルに対し
て、必要に応じて、偏光板、カラー偏光板、光源、カラ
ーフィルタ、半透過反射板、反射板、導光板、紫外線カ
ットフィルタ等を積層する、文字、図形等を印刷する、
またはノングレア加工するなどして液晶素子が製造され
る。A liquid crystal composition containing the optically active compound (1) of the present invention is injected into the empty cell, and the injection port is sealed with a sealing agent to form a liquid crystal cell. On this liquid crystal cell, as necessary, a polarizing plate, a color polarizing plate, a light source, a color filter, a semi-transmissive reflecting plate, a reflecting plate, a light guide plate, a UV cut filter, etc. are laminated, and characters, figures, etc. are printed. ,
Alternatively, a liquid crystal element is manufactured by non-glare processing or the like.

【００４３】本発明の光学活性化合物（１）はらせん誘
起力が大きいため、液晶組成物に添加する際に、従来の
光学活性化合物より少量の添加で、目的とするらせんピ
ッチを持つ液晶組成物が得られる。また、同時に、光学
活性化合物（１）は誘電率異方性（Δε）が大きいこと
により、これを液晶組成物に添加した場合に、従来の光
学活性化合物を用いる場合よりもΔεが大きい液晶組成
物が得られ、従来の光学活性化合物を用いる場合よりも
低い駆動電圧で駆動することができる。Since the optically active compound (1) of the present invention has a large helical inducing force, it can be added to a liquid crystal composition by adding a smaller amount than a conventional optically active compound and having a desired helical pitch. Is obtained. At the same time, since the optically active compound (1) has a large dielectric anisotropy (Δε), when the compound is added to the liquid crystal composition, the liquid crystal composition has a larger Δε than when the conventional optically active compound is used. And can be driven with a lower driving voltage than when a conventional optically active compound is used.

【００４４】光学活性化合物（１）を含有する液晶組成
物を用いてＴＮ型またはＳＴＮ型液晶表示素子とした場
合には、均一なツイスト配向を達成でき、反射コレステ
リック型液晶素子とした場合には、目的とする反射波長
が得られる。また、光学活性化合物（１）を含有する液
晶組成物は、アクティブマトリクス素子、高分子分散型
液晶素子、多色性色素を用いたＧＨ型液晶素子、強誘電
性液晶素子等の種々の方式でも使用できる。また、調光
素子、調光窓、光シャッタ、偏光交換素子、光学カラー
フィルタ、着色フィルム、光学記録素子、温度指示計等
の表示用途以外にも使用できる。When a liquid crystal composition containing the optically active compound (1) is used to form a TN type or STN type liquid crystal display device, a uniform twist alignment can be achieved, and when a reflective cholesteric type liquid crystal device is used. And the intended reflection wavelength can be obtained. Further, the liquid crystal composition containing the optically active compound (1) can be prepared by various methods such as an active matrix element, a polymer dispersed liquid crystal element, a GH type liquid crystal element using a polychromatic dye, and a ferroelectric liquid crystal element. Can be used. Further, it can be used for purposes other than display such as a light control element, a light control window, an optical shutter, a polarization exchange element, an optical color filter, a colored film, an optical recording element, and a temperature indicator.

【００４５】[0045]

【実施例】［実施例１］（Ｒ）−４−（２−フェニルプ
ロピル）安息香酸（４−シアノ−３，５−ジフルオロ）
フェニル［H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CN］の合
成。＜第１ステップ＞１０Ｌの四つ口フラスコに（Ｓ）−２
−フェニルプロピオン酸６００ｇ（４．００ｍｏｌ）、
テトラクロロエチレン２．４Ｌ、塩化チオニル９５１ｇ
（８．００ｍｏｌ）、ジメチルアニリン少量を加え室温
で一晩撹拌した後、過剰な塩化チオニル、テトラクロロ
エチレンを減圧留去し、（Ｓ）−２−フェニルプロピオ
ン酸クロリド６９１ｇを得た。EXAMPLES Example 1 (R) -4- (2-phenylpropyl) benzoic acid (4-cyano-3,5-difluoro)
Synthesis of phenyl [H-Ph-CH (CH 3) -CH 2 -Ph-COO-Ph FF -CN]. <First Step> (S) -2 in a 10 L four-necked flask
-Phenylpropionic acid 600 g (4.00 mol),
2.4 L of tetrachloroethylene, 951 g of thionyl chloride
(8.00 mol) and a small amount of dimethylaniline were added, and the mixture was stirred at room temperature overnight. Then, excess thionyl chloride and tetrachloroethylene were distilled off under reduced pressure to obtain 691 g of (S) -2-phenylpropionic acid chloride.

【００４６】１０Ｌの四つ口フラスコ（フラスコＡ）
に、マグネシウム片１０２ｇ（４．２０ｍｏｌ）、無水
テトラヒドロフラン２００ｍＬと少量のヨウ素末を加
え、窒素雰気下で１−ブロモ−４−クロロベンゼン７６
５ｇ（４．００ｍｏｌ）を無水テトラヒドロフラン７．
８Ｌに溶解させた溶液を少量滴下し、ヨウ素の色が消え
た時点で反応が開始したとして、反応温度を３０℃以下
に保ちながら残りの溶液を３時間で滴下し、滴下終了後
室温で１時間撹拌し、グリニヤール試薬を調製した。10 L four-necked flask (flask A)
To the mixture were added 102 g (4.20 mol) of magnesium pieces, 200 mL of anhydrous tetrahydrofuran and a small amount of iodine powder, and 1-bromo-4-chlorobenzene 76 in a nitrogen atmosphere.
5 g (4.00 mol) of anhydrous tetrahydrofuran 7.
A small amount of the solution dissolved in 8 L was added dropwise, and the reaction was started when the iodine color disappeared. The remaining solution was added dropwise over 3 hours while maintaining the reaction temperature at 30 ° C. or lower. After stirring for an hour, a Grignard reagent was prepared.

【００４７】２０Ｌの四つ口フラスコ（フラスコＢ）
に、（Ｓ）−２−フェニルプロピオン酸クロリド６９１
ｇ、トルエン４．４Ｌを入れ、窒素雰気下で−１０℃に
冷却し、鉄（III）アセチルアセトナート１．４１ｇ
（４．００ｍｍｏｌ）を加えた。反応温度を−１０℃以
下に保ちながら、窒素雰気下フラスコＡで調製したグリ
ニヤール試薬を４時間で滴下し、滴下終了後室温まで昇
温して一晩撹拌した後、１０℃に冷却し、希塩酸４Ｌを
加えた。20 L four-necked flask (flask B)
In addition, (S) -2-phenylpropionic acid chloride 691
g, 4.4 L of toluene and cooled to −10 ° C. in a nitrogen atmosphere, and 1.41 g of iron (III) acetylacetonate
(4.00 mmol) was added. While maintaining the reaction temperature at -10 ° C or lower, the Grignard reagent prepared in Flask A under a nitrogen atmosphere was added dropwise over 4 hours. 4 L of dilute hydrochloric acid was added.

【００４８】次いで、有機層を分離し、水層はトルエン
で抽出し、有機層を合わせて水、飽和食塩水で洗浄し、
無水硫酸マグネシウムで乾燥した後、溶媒を留去して粗
生成物を得た。これをシリカゲルカラムクロマトグラフ
ィー（展開溶媒：ヘキサン、トルエン）で精製し、エタ
ノールから再結晶し、（Ｓ）−１−（４−クロロフェニ
ル）−２−フェニルプロパン−１−オン［H-Ph-CH(CH₃)
-CO-Ph-Cl］の白色結晶３２９ｇ（１．３４ｍｏｌ）を
得た。（収率３４％）ＭＳ m/e：２４４（Ｍ⁺）Next, the organic layer was separated, the aqueous layer was extracted with toluene, and the combined organic layers were washed with water and saturated saline,
After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain a crude product. This was purified by silica gel column chromatography (developing solvent: hexane, toluene), recrystallized from ethanol, and (S) -1- (4-chlorophenyl) -2-phenylpropan-1-one [H-Ph-CH (CH ₃ )
329 g (1.34 mol) of white crystals of -CO-Ph-Cl] were obtained. (Yield 34%) MS m / e: 244 (M ⁺ )

【００４９】＜第２ステップ＞５Ｌの四つ口フラスコ
に、第１ステップで得た（Ｓ）−１−（４−クロロフェ
ニル）−２−フェニルプロパン−１−オン［H-Ph-CH(CH
₃)-CO-Ph-Cl］３２０ｇ（１．３１ｍｏｌ）、トリフル
オロ酢酸１．４９ｋｇ（１３．１ｍｏｌ）を加え、０℃
に冷却し、トリエチルシラン３８０ｇ（３．２７ｍｏ
ｌ）を反応温度を５℃以下に保ちながら１時間で滴下
し、滴下終了後室温まで昇温して３時間撹拌した。<Second Step> The (S) -1- (4-chlorophenyl) -2-phenylpropan-1-one obtained in the first step [H-Ph-CH (CH)
₃ ) -CO-Ph-Cl], 320 g (1.31 mol) and 1.49 kg (13.1 mol) of trifluoroacetic acid, and the mixture was added at 0 ° C.
380 g of triethylsilane (3.27 mol)
1) was added dropwise over 1 hour while maintaining the reaction temperature at 5 ° C. or lower, and after completion of the addition, the mixture was heated to room temperature and stirred for 3 hours.

【００５０】次いで、トルエン１Ｌを加え、減圧下でト
リフルオロ酢酸を留去した後、トルエン１Ｌ加え、５％
炭酸水素ナトリウム水溶液、水、飽和食塩水で洗浄し、
無水硫酸マグネシウムで乾燥し、溶媒および複生成物を
留去して粗生成物を得た。これをシリカゲルカラムクロ
マトグラフィー（展開溶媒：ヘキサン）で精製し、
（Ｒ）−１−（４−クロロフェニル）−２−フェニルプ
ロパン［H-Ph-CH(CH₃)-CH₂-Ph-Cl］の無色の液体２１９
ｇ（９４９ｍｍｏｌ）を得た。（収率７２％）ＭＳ m/e：２３０（Ｍ⁺）Next, 1 L of toluene was added, and trifluoroacetic acid was distilled off under reduced pressure.
Washed with aqueous sodium bicarbonate, water and saturated saline,
After drying over anhydrous magnesium sulfate, the solvent and the double product were distilled off to obtain a crude product. This is purified by silica gel column chromatography (developing solvent: hexane),
(R) -1- (4- chlorophenyl) -2-phenylpropane [H-Ph-CH (CH 3) -CH 2 -Ph-Cl] colorless liquid 219
g (949 mmol) was obtained. (Yield 72%) MS m / e: 230 (M ⁺ )

【００５１】＜第３ステップ＞１Ｌの四ッ口フラスコ
に、マグネシウム片１１．１ｇ（４５５ｍｍｏｌ）、無
水テトラヒドロフラン２０ｍＬと少量のヨウ素粉末を加
えた。臭化エチル２３．６ｇ（２１７ｍｍｏｌ）を無水
テトラヒドロフラン１２４ｍＬに溶解させた溶液を窒素
雰囲気下で少量滴下し、ヨウ素の色が消えた時点で、反
応温度を２５℃以下に保ちながら残りの溶液を１時間で
滴下し、滴下終了後室温で１時間撹拌した後、第２ステ
ップで得た（Ｒ）−１−（４−クロロフェニル）−２−
フェニルプロパン［H-Ph-CH(CH₃)-CH₂-Ph-Cl］５０ｇ
（２１７ｍｍｏｌ）を加え、加熱環流下で６時間撹拌し
た。<Third Step> To a 1 L four-necked flask, 11.1 g (455 mmol) of magnesium pieces, 20 mL of anhydrous tetrahydrofuran and a small amount of iodine powder were added. A solution prepared by dissolving 23.6 g (217 mmol) of ethyl bromide in 124 mL of anhydrous tetrahydrofuran was added dropwise in a small amount under a nitrogen atmosphere. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour, and then the (R) -1- (4-chlorophenyl) -2- obtained in the second step.
Phenylpropane [H-Ph-CH (CH 3) -CH 2 -Ph-Cl] 50g
(217 mmol) was added, and the mixture was stirred under heated reflux for 6 hours.

【００５２】次いで、無水テトラヒドロフラン２９０ｍ
Ｌを加え、−３０℃に冷却し、−２０℃以下に保ちなが
ら炭酸ガスを吹き込み、発熱が無くなった後に炭酸ガス
を吹き込み続けながら室温まで昇温した。反応溶液を氷
冷した希塩酸に注ぎ、未反応のマグネシウムをろ過した
後に、有機相を分離し、水相をメチル−ｔ−ブチルエー
テルで抽出し、有機相とあわせて水、飽和食塩水で洗浄
し、無水硫酸ナトリウムで乾燥し、溶媒および副生成物
を留去して粗生成物の結晶を得た。これをトルエンから
再結晶して（Ｒ）−４−（２−フェニルプロピル）安息
香酸［H-Ph-CH(CH₃)-CH₂-Ph-COOH］の白色結晶４４．３
ｇ（１８４ｍｍｏｌ）を得た（収率８５％）。Next, 290 m of anhydrous tetrahydrofuran
L was added, the mixture was cooled to −30 ° C., and carbon dioxide gas was blown therein while maintaining the temperature at −20 ° C. or lower. The reaction solution was poured into ice-cooled diluted hydrochloric acid, and after filtering unreacted magnesium, the organic phase was separated. After drying over anhydrous sodium sulfate, the solvent and by-products were distilled off to obtain crystals of a crude product. This white crystal was recrystallized from toluene (R) -4- (2- phenylpropyl) benzoic acid [H-Ph-CH (CH 3) -CH 2 -Ph-COOH] 44.3
g (184 mmol) was obtained (85% yield).

【００５３】＜第４ステップ＞２００ｍＬのなすフラス
コに対して、第３ステップで得た（Ｒ）−４−（２−フ
ェニルプロピル）安息香酸［H-Ph-CH(CH₃)-CH₂-Ph-COO
H］２０．０ｇ（８３．２ｍｍｏｌ）、テトラクロロエ
チレン８０ｍＬ、塩化チオニル１９．８ｇ（１６６ｍｍ
ｏｌ）を加え７０℃で３時間撹拌した後、過剰な塩化チ
オニル、テトラクロロエチレンを減圧留去し、（Ｒ）−
４−（２−フェニルプロピル）安息香酸クロリド［H-Ph
-CH(CH₃)-CH₂-Ph-COCl］２２．０ｇを得た。<Fourth Step> The (R) -4- (2-phenylpropyl) benzoic acid [H-Ph-CH (CH ₃ ) -CH ₂ -obtained in the third step was placed in a 200-mL eggplant flask. Ph-COO
H] 20.0 g (83.2 mmol), tetrachloroethylene 80 mL, thionyl chloride 19.8 g (166 mm
ol) and stirred at 70 ° C. for 3 hours, and then excess thionyl chloride and tetrachloroethylene were distilled off under reduced pressure to obtain (R)-
4- (2-phenylpropyl) benzoic acid chloride [H-Ph
-CH (CH ₃₎ to give the -CH ₂ -Ph-COCl] 22.0g.

【００５４】２００ｍＬの四つ口フラスコに、（Ｒ）−
４−（２−フェニルプロピル）安息香酸クロリド［H-Ph
-CH(CH₃)-CH₂-Ph-COCl］２２．０ｇ、トルエン１０３ｍ
ｌ、３，５−ジフルオロ−４−シアノフェノール１２．
９ｇ（８３．２ｍｍｏｌ）、ピリジン７．９０ｇ（９
９．９ｍｍｏｌ）を加え、室温で一晩撹拌した。反応溶
液に水を加えて有機層を分離し、水層はトルエンで抽出
し、有機層を合わせて、希塩酸、炭酸水素ナトリウム水
溶液、飽和食塩水で洗浄し、無水硫酸マグネシウムで乾
燥し、溶媒を留去して粗生成物を得た。In a 200 mL four-necked flask, (R)-
4- (2-phenylpropyl) benzoic acid chloride [H-Ph
-CH (CH ₃ ) -CH ₂ -Ph-COCl] 22.0 g, toluene 103 m
l, 3,5-difluoro-4-cyanophenol12.
9 g (83.2 mmol), pyridine 7.90 g (9
9.9 mmol) and stirred overnight at room temperature. Water was added to the reaction solution, and the organic layer was separated.The aqueous layer was extracted with toluene. Evaporation gave a crude product.

【００５５】上記粗生成物を、シリカゲルカラムクロマ
トグラフィー（展開溶媒：ヘキサン／トルエン＝３／
１）を用いて精製し、エタノールから再結晶して（Ｒ）
−４−（２−フェニルプロピル）安息香酸（４−シアノ
−３，５−ジフルオロ）フェニル［H-Ph-CH(CH₃)-CH₂-P
h-COO-Ph^FF-CN］の白色結晶２３．６ｇ（６２．４ｍｍ
ｏｌ）を得た。（収率７５％） H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CN・・・式（４）融点：６５．３〜６６．１℃ ＭＳｍ／ｅ：３７７（Ｍ⁺）¹ Ｈ−ＮＭＲ（ＣＤＣｌ₃） δ（ｐｐｍ：ｆｒｏｍＴＭ
Ｓ）：１．２９（ｄ，３Ｈ），２．８８−３．１１
（ｍ，３Ｈ），７．０３（ｄ，２Ｈ），７．１３−７．
３０（ｍ，７Ｈ），７．９９（ｄ，２Ｈ）¹⁹ Ｆ−ＮＭＲ（ＣＤＣｌ₃） δ（ｐｐｍ：ｆｒｏｍＣ
ＦＣｌ₃）：−１０２．７（ｄ，Ｊ_F-H＝６．１Ｈｚ）The above crude product was subjected to silica gel column chromatography (developing solvent: hexane / toluene = 3 /
Purified using 1), recrystallized from ethanol and (R)
4- (2-phenylpropyl) benzoic acid (4-cyano-3,5-difluorophenyl) phenyl [H-Ph-CH (CH 3) -CH 2 -P
h-COO-Ph ^FF -CN] 23.6 g (62.4 mm
ol). (75% yield) H-Ph-CH (CH 3) -CH 2 -Ph-COO-Ph FF -CN ··· Equation (4) Melting point: 65.3~66.1 ℃ MS m / e: 377 (M ⁺ ) ¹ H-NMR (CDCl ₃ ) δ (ppm: fromTM
S): 1.29 (d, 3H), 2.88-3.11
(M, 3H), 7.03 (d, 2H), 7.13-7.
30 (m, 7H), 7.99 (d, 2H) ¹⁹ F-NMR (CDCl ₃ ) δ (ppm: fromC
FCl ₃ ): -102.7 (d, J _FH = 6.1 Hz)

【００５６】［実施例２］（Ｒ）−４−（２−フェニル
プロピル）安息香酸（４−シアノ−３フルオロ）フェニ
ル［H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^F-CN］の合成。実施例１の第４ステップにおいて、３，５−ジフルオロ
−４−シアノフェノールのかわりに、３−フルオロ−４
−シアノフェノール１１．４ｇ（８３．２ｍｍｏｌ）を
用いる以外は実施例１の第４ステップと同様に反応を行
い、（Ｒ）−４−（２−フェニルプロピル）安息香酸
（４−シアノ−３フルオロ）フェニル［H-Ph-CH(CH₃)-C
H₂-Ph-COO-Ph^F-CN］の白色結晶２１．５ｇ（５９．９ｍ
ｍｏｌ）を得た。（収率７２％） H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^F-CN・・・式（３）融点：７７．９〜７９．１℃ ＭＳｍ／ｅ：３５９（Ｍ⁺）¹ Ｈ−ＮＭＲ（ＣＤＣｌ₃） δ（ｐｐｍ：ｆｒｏｍＴＭ
Ｓ）：１．３０（ｄ，３Ｈ），２．８９−３．０９
（ｍ，３Ｈ），７．１４−７．３０（ｍ，９Ｈ），７．
６７（ｔ，１Ｈ），８．０１（ｄ，２Ｈ）¹⁹ Ｆ−ＮＭＲ（ＣＤＣｌ₃） δ（ｐｐｍ：ｆｒｏｍＣ
ＦＣｌ₃）：−１０３．９（ｔ，Ｊ_F-H＝９．２Ｈｚ）Example 2 (R) -4- (2-phenylpropyl) benzoic acid (4-cyano-3fluoro) phenyl [H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^F- CN]. In the fourth step of Example 1, instead of 3,5-difluoro-4-cyanophenol, 3-fluoro-4
-Reaction was carried out in the same manner as in the fourth step of Example 1 except that 11.4 g (83.2 mmol) of cyanophenol was used, and (R) -4- (2-phenylpropyl) benzoic acid (4-cyano-3fluoro) was used. ) Phenyl [H-Ph-CH (CH ₃ ) -C
H ₂ -Ph-COO-Ph ^F -CN] 21.5 g (59.9 m
mol). (72% yield) H-Ph-CH (CH 3) -CH 2 -Ph-COO-Ph F -CN ··· Equation (3) Melting point: 77.9~79.1 ℃ MS m / e: 359 (M ⁺ ) ¹ H-NMR (CDCl ₃ ) δ (ppm: fromTM
S): 1.30 (d, 3H), 2.89-3.09
(M, 3H), 7.14-7.30 (m, 9H), 7.
67 (t, 1H), 8.01 (d, 2H) ¹⁹ F-NMR (CDCl ₃ ) δ (ppm: fromC
_{FCl 3): - 103.9 (t} , J FH = 9.2Hz)

【００５７】［実施例３］（Ｒ）−２，６−ジフルオロ
−４−（４−（２−フェニルプロピル）フェニル）ベン
ゾニトリル［H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CN］の合成。＜第１ステップ＞１Ｌの四ッ口フラスコ（フラスコＡ）
に、マグネシウム片１２．６ｇ（５２０ｍｍｏｌ）、無
水テトラヒドロフラン３０ｍＬと少量のヨウ素粉末を加
えた。臭化エチル４．７２ｇ（４３．３ｍｍｏｌ）を無
水テトラヒドロフラン２０ｍＬに溶解させた溶液を窒素
雰囲気下で少量滴下した。Example 3 (R) -2,6-difluoro-4- (4- (2-phenylpropyl) phenyl) benzonitrile [H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF- CN]. <First step> 1 L four-necked flask (flask A)
To the mixture, 12.6 g (520 mmol) of magnesium pieces, 30 mL of anhydrous tetrahydrofuran and a small amount of iodine powder were added. A solution of 4.72 g (43.3 mmol) of ethyl bromide in 20 mL of anhydrous tetrahydrofuran was added dropwise in a small amount under a nitrogen atmosphere.

【００５８】ヨウ素の色が消えた時点で、反応温度を２
５℃以下に保ちながら残りの溶液を滴下し、滴下終了後
実施例１の第２ステップで得た（Ｒ）−１−（４−クロ
ロフェニル）−２−フェニルプロパン［H-Ph-CH(CH₃)-C
H₂-Ph-Cl］１００ｇ（４３３ｍｍｏｌ）を無水テトラヒ
ドロフラン１１０ｍＬに溶解させた溶液を加え、加熱環
流下で６時間撹拌した後、室温まで冷却し、無水テトラ
ヒドロフラン３２０ｍＬを加えてグリニヤール試薬を調
製した。When the iodine color disappeared, the reaction temperature was raised to 2
The remaining solution was added dropwise while maintaining the temperature at 5 ° C. or lower, and after completion of the addition, the (R) -1- (4-chlorophenyl) -2-phenylpropane [H-Ph-CH (CH) ₃ ) -C
A solution prepared by dissolving 100 g (433 mmol) of [H ₂ -Ph-Cl] in 110 mL of anhydrous tetrahydrofuran was added, and the mixture was stirred under reflux with heating for 6 hours. After cooling to room temperature, 320 mL of anhydrous tetrahydrofuran was added to prepare a Grignard reagent.

【００５９】１Ｌの四つ口フラスコ（フラスコＢ）に、
ホウ酸トリメチル５４．０ｇ（５２０ｍｍｏｌ）、無水
テトラヒドロフラン１０８ｍＬを加え、−３０℃に冷却
し、窒素雰気下−３０℃以下に保ちながらフラスコＡで
調整したグリニヤール試薬を３０分で滴下し、滴下終了
後室温まで昇温し室温で一晩撹拌した。反応溶液に希塩
酸を加え、室温で一時間撹拌した後に、有機相を分離
し、水相をメチル−ｔ−ブチルエーテルで抽出し、有機
相とあわせて水、飽和食塩水で洗浄し、無水硫酸ナトリ
ウムで乾燥し、溶媒を留去して（Ｒ）−４−（２−フェ
ニルプロピル）フェニルホウ酸［H-Ph-CH(CH₃)-CH₂-Ph-
B(OH)₂］９２．６ｇ（３８６ｍｍｏｌ）を得た（収率８
９％）。In a 1 L four-necked flask (flask B),
After adding 54.0 g (520 mmol) of trimethyl borate and 108 mL of anhydrous tetrahydrofuran, the mixture was cooled to −30 ° C., and the Grignard reagent prepared in Flask A was added dropwise in 30 minutes while maintaining the temperature at −30 ° C. or lower in a nitrogen atmosphere, and the dropwise addition was completed. Thereafter, the temperature was raised to room temperature, and the mixture was stirred at room temperature overnight. Dilute hydrochloric acid was added to the reaction solution, and after stirring at room temperature for 1 hour, the organic phase was separated, the aqueous phase was extracted with methyl-t-butyl ether, and the organic phase was washed with water and saturated saline together with anhydrous sodium sulfate. in dried and evaporated (R) -4- (2- phenylpropyl) phenylboronic acid [H-Ph-CH (CH 3) -CH 2 -Ph-
B (OH) ₂ ] 92.6 g (386 mmol) was obtained (yield 8
9%).

【００６０】＜第２ステップ＞１Ｌの四ッ口フラスコ
に、第１ステップで得た（Ｒ）−４−（２−フェニルプ
ロピル）フェニルホウ酸［H-Ph-CH(CH₃)-CH₂-Ph-B(O
H)₂］５０．０ｇ（２０８ｍｍｏｌ）、１−ブロモ−
３，５−ジフルオロベンゼン４０．２ｇ（２０８ｍｍｏ
ｌ）、テトラキストリフェニルホスフィンパラジウム
［Pd(PPh₃)₄］１２．０ｇ（１０．４ｍｍｏｌ）、２ｍ
ｏｌ／Ｌ炭酸ナトリウム水溶液３００ｍＬ、１，２−ジ
メトキシエタン３００ｍＬを加え、加熱環流下で４時間
撹拌した。[0060] The four-neck flask <Second step> 1L, obtained in the first step (R) -4- (2- phenylpropyl) phenylboronic acid [H-Ph-CH (CH 3) -CH 2 - Ph-B (O
H) ₂ ] 50.0 g (208 mmol), 1-bromo-
40.2 g of 3,5-difluorobenzene (208 mmol
1), 12.0 g (10.4 mmol) of tetrakistriphenylphosphine palladium [Pd (PPh ₃ ) ₄ ], 2 m
ol / L aqueous sodium carbonate solution (300 mL) and 1,2-dimethoxyethane (300 mL) were added, and the mixture was stirred for 4 hours under heated reflux.

【００６１】次いで、室温まで冷却し、反応溶液にトル
エンを加えて有機層を分離し、水層はトルエンで抽出
し、有機層を合わせて、水、飽和食塩水で洗浄し、無水
硫酸マグネシウムで乾燥し、溶媒を留去して粗生成物を
得た。これをシリカゲルカラムクロマトグラフィー（展
開溶媒：ヘキサン）を用いて精製し、エタノールから再
結晶して（Ｒ）−３，５−ジフルオロ−１−（４−（２
−フェニルプロピル）フェニル）ベンゼン［H-Ph-CH(CH
₃)-CH₂-Ph-Ph^FF-H］の白色結晶３５．３ｇ（１１５ｍｍ
ｏｌ）を得た。（収率５５％）融点：４９．８〜５１．３℃ ＭＳｍ／ｅ：３０８（Ｍ⁺）¹ Ｈ−ＮＭＲ（ＣＤＣｌ₃） δ（ｐｐｍ：ｆｒｏｍＴＭ
Ｓ）：１．２７（ｄ，３Ｈ），２．７８−２．８５
（ｍ，１Ｈ），２．９４−３．０７（ｍ，２Ｈ），６．
７４（ｔ，１Ｈ），７．０５−７．３１（ｍ，９Ｈ），
７．４０（ｄ，２Ｈ）¹⁹Ｆ−ＮＭＲ（ＣＤＣｌ₃） δ
（ｐｐｍ：ｆｒｏｍＣＦＣｌ₃）：−１１０．４（ｔ，
Ｊ_F-H＝７．６Ｈｚ）Next, the reaction solution was cooled to room temperature, toluene was added to the reaction solution, and the organic layer was separated. The aqueous layer was extracted with toluene. After drying, the solvent was distilled off to obtain a crude product. This was purified using silica gel column chromatography (developing solvent: hexane), and recrystallized from ethanol to give (R) -3,5-difluoro-1- (4- (2
-Phenylpropyl) phenyl) benzene [H-Ph-CH (CH
_{_{^{3) -CH 2 -Ph-Ph FF}}} -H] as white crystals 35.3 g (115 mm
ol). (Yield 55%) Melting point: 49.8-51.3 ° C MS m / e: 308 (M ⁺ ) ¹ H-NMR (CDCl ₃ ) δ (ppm: fromTM)
S): 1.27 (d, 3H), 2.78-2.85
(M, 1H), 2.94-3.07 (m, 2H), 6.
74 (t, 1H), 7.05-7.31 (m, 9H),
7.40 (d, 2H) ¹⁹ F-NMR (CDCl ₃ ) δ
_{(Ppm: fromCFCl 3): -} 110.4 (t,
J _FH = 7.6 Hz)

【００６２】＜第３ステップ＞５００ｍＬの四ッ口フラ
スコに、第２ステップで得た（Ｒ）−３，５−ジフルオ
ロ−１−（４−（２−フェニルプロピル）フェニル）ベ
ンゼン［H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-H］３５．０ｇ（１
１４ｍｍｏｌ）、無水テトラヒドロフラン１７５ｍＬを
加え、窒素雰囲気下−７０℃に冷却し、反応温度を−６
０℃以下に保ちながら１．５２ｍｏｌ／Ｌｎ−ブチルリ
チウムヘキサン溶液９０ｍＬ（１３６ｍｍｏｌ）を３０
分で滴下し、滴下終了後−７０℃で２時間撹拌した後、
−６０℃以下に保ちながら炭酸ガスを吹き込み、発熱が
無くなった後に炭酸ガスを吹き込み続けながら室温まで
昇温した。<Third Step> The (R) -3,5-difluoro-1- (4- (2-phenylpropyl) phenyl) benzene obtained in the second step is placed in a 500 mL four-necked flask [H-Ph]. -CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -H] 35.0 g (1
14 mmol) and 175 mL of anhydrous tetrahydrofuran, and the mixture was cooled to −70 ° C. under a nitrogen atmosphere.
While maintaining the temperature at 0 ° C. or lower, 90 mL (136 mmol) of a 1.52 mol / L n-butyllithium hexane solution was added to 30
After stirring for 2 hours at -70 ° C after completion of the dropping,
While maintaining the temperature at -60 ° C or lower, carbon dioxide gas was blown, and after heat generation was stopped, the temperature was raised to room temperature while continuously blowing the carbon dioxide gas.

【００６３】次いで、反応溶液に希塩酸を加え、有機相
を分離し、水相をメチル−ｔ−ブチルエーテルで抽出
し、有機相とあわせて水、飽和食塩水で洗浄し、無水硫
酸ナトリウムで乾燥し、溶媒を留去して粗生成物の結晶
を得た。これをトルエンから再結晶して（Ｒ）−２，６
−ジフルオロ−４−（４−（２−フェニルプロピル）フ
ェニル）安息香酸［H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-COOH］
の白色結晶３１．２ｇ（８８．５ｍｍｏｌ）を得た（収
率７８％）。Next, dilute hydrochloric acid was added to the reaction solution, the organic phase was separated, the aqueous phase was extracted with methyl-t-butyl ether, and the combined organic phase was washed with water and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a crude product crystal. This was recrystallized from toluene to give (R) -2,6
- difluoro-4- (4- (2-phenylpropyl) phenyl) benzoic acid [H-Ph-CH (CH 3) -CH 2 -Ph-Ph FF -COOH]
31.2 g (88.5 mmol) of white crystals were obtained (78% yield).

【００６４】＜第４ステップ＞３００ｍＬのなすフラス
コに第３ステップで得た（Ｒ）−２，６−ジフルオロ−
４−（４−（２−フェニルプロピル）フェニル）安息香
酸［H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-COOH］３０．０ｇ（８
５．１ｍｍｏｌ）、テトラクロロエチレン１２０ｍＬ、
塩化チオニル２０．３ｇ（１７０ｍｍｏｌ）を加え９０
℃で４時間撹拌した後、過剰な塩化チオニル、テトラク
ロロエチレンを減圧留去し、（Ｒ）−２，６−ジフルオ
ロ−４−（４−（２−フェニルプロピル）フェニル）安
息香酸クロリド［H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-COCl］３
２．５ｇを得た。<Fourth Step> The (R) -2,6-difluoro- obtained in the third step was placed in a 300 mL eggplant flask.
4- (4- (2-phenylpropyl) phenyl) benzoic acid [H-Ph-CH (CH 3) -CH 2 -Ph-Ph FF -COOH] 30.0g (8
5.1 mmol), 120 mL of tetrachloroethylene,
Add 20.3 g (170 mmol) of thionyl chloride and add 90
After stirring at 4 ° C. for 4 hours, excess thionyl chloride and tetrachloroethylene were distilled off under reduced pressure, and (R) -2,6-difluoro-4- (4- (2-phenylpropyl) phenyl) benzoic acid chloride [H-Ph _{_{-CH (CH 3) -CH 2 -Ph}} -Ph FF -COCl] 3
2.5 g were obtained.

【００６５】５００ｍＬの四つ口フラスコに、トルエン
７３ｍＬ、２５％アンモニア水２６ｍＬを加え、１０℃
に冷却し、（Ｒ）−２，６−ジフルオロ−４−（４−
（２−フェニルプロピル）フェニル）安息香酸クロリド
［H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-COCl］３２．５ｇをトル
エン１３３ｍＬに溶解させた溶液を１５℃以下に保ちな
がら３０分で滴下し、滴下終了後室温で１時間撹拌し
た。析出した（Ｒ）−２，６−ジフルオロ−４−（４−
（２−フェニルプロピル）フェニル）ベンズアミド［H-
Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CONH₂］の結晶を反応溶液から
ろ過し、結晶を水で洗浄した。To a 500 mL four-necked flask, 73 mL of toluene and 26 mL of 25% aqueous ammonia were added, and 10 ° C.
And cooled to (R) -2,6-difluoro-4- (4-
A solution prepared by dissolving 32.5 g of (2-phenylpropyl) phenyl) benzoic acid chloride [H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -COCl] in 133 mL of toluene was maintained at 15 ° C. or lower. The mixture was added dropwise over 30 minutes, and after completion of the addition, the mixture was stirred at room temperature for 1 hour. The precipitated (R) -2,6-difluoro-4- (4-
(2-phenylpropyl) phenyl) benzamide [H-
The crystals of _{Ph-CH (CH 3) -CH} 2 -Ph-Ph FF -CONH 2] was filtered from the reaction solution, and the crystals were washed with water.

【００６６】５００ｍＬ四つ口フラスコに、（Ｒ）−
２，６−ジフルオロ−４−（４−（２−フェニルプロピ
ル）フェニル）ベンズアミド［H-Ph-CH(CH₃)-CH₂-Ph-Ph
^FF-CONH₂］の結晶とトルエン１４２ｍＬを加え、加熱還
流下ディーンスタークを用いて共沸脱水を行った後、ｐ
−トルエンスルホン酸クロリド２４．３ｇ（１２８ｍｍ
ｏｌ）、ピリジン２０．２ｇ（２５５ｍｍｏｌ）を加
え、加熱還流下２０時間撹拌した。In a 500 mL four-necked flask, (R)-
2,6-difluoro-4- (4- (2-phenylpropyl) phenyl) benzamide [H-Ph-CH (CH 3) -CH 2 -Ph-Ph
^FF- CONH ₂ ] and 142 mL of toluene were added, and the mixture was subjected to azeotropic dehydration using Dean Stark under reflux with heating.
-24.3 g of toluenesulfonic acid chloride (128 mm
ol) and pyridine (20.2 g, 255 mmol) were added, and the mixture was stirred under heating and reflux for 20 hours.

【００６７】次いで、反応溶液に水を加えて有機層を分
離し、水層はトルエンで抽出し、有機層を合わせて、希
塩酸で洗浄し、５％水酸化ナトリウム水溶液を加え室温
で一晩撹拌した後水層を分離し、飽和食塩水で洗浄し、
無水硫酸マグネシウムで乾燥し、溶媒を留去して粗生成
物を得た。これをシリカゲルカラムクロマトグラフィー
（展開溶媒：ヘキサン）を用いて精製し、エタノールか
ら再結晶して（Ｒ）−２，６−ジフルオロ−４−（４−
（２−フェニルプロピル）フェニル）ベンゾニトリル
［H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CN］の白色結晶１８．７
ｇ（５６．２ｍｍｏｌ）を得た。（収率６６％） H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CN・・・式（２）融点：６０．７〜６２．２℃ ＭＳｍ／ｅ：３３３（Ｍ⁺）¹ Ｈ−ＮＭＲ（ＣＤＣｌ₃） δ（ｐｐｍ：ｆｒｏｍＴＭ
Ｓ）：１．２８（ｄ，３Ｈ），２．８２−２．９１
（ｍ，１Ｈ），２．９５−３．０７（ｍ，２Ｈ），７．
１６−７．３１（ｍ，９Ｈ），７．４２（ｄ，２Ｈ）¹⁹ Ｆ−ＮＭＲ（ＣＤＣｌ₃） δ（ｐｐｍ：ｆｒｏｍＣ
ＦＣｌ₃）：−１０４．３（ｄ，Ｊ_F-H＝９．２Ｈｚ）Next, water was added to the reaction solution to separate an organic layer, and the aqueous layer was extracted with toluene. The organic layers were combined, washed with diluted hydrochloric acid, added with a 5% aqueous sodium hydroxide solution, and stirred at room temperature overnight. After that, the aqueous layer was separated and washed with saturated saline,
After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain a crude product. This was purified using silica gel column chromatography (developing solvent: hexane), and recrystallized from ethanol to give (R) -2,6-difluoro-4- (4-
(2-phenylpropyl) phenyl) white crystals benzonitrile [H-Ph-CH (CH 3) -CH 2 -Ph-Ph FF -CN] 18.7
g (56.2 mmol) were obtained. (66% yield) H-Ph-CH (CH 3) -CH 2 -Ph-Ph FF -CN ··· formula (2) Melting point: 60.7~62.2 ℃ MS m / e: 333 (M ⁺ ) ¹ H-NMR (CDCl ₃ ) δ (ppm: fromTM)
S): 1.28 (d, 3H), 2.82-2.91
(M, 1H), 2.95-3.07 (m, 2H), 7.
16-7.31 (m, 9H), 7.42 (d, 2H) ¹⁹ F-NMR (CDCl ₃ ) δ (ppm: fromC
FCl ₃ ): -104.3 (d, J _FH = 9.2 Hz)

【００６８】［実施例４］（Ｒ）−２−フルオロ−４−
（４−（２−フェニルプロピル）フェニル）ベンゾトリ
フルオリド［H-Ph-CH(CH₃)-CH₂-Ph-Ph^F-CF₃］の合成。実施例３の第２ステップにおいて、１−ブロモ−３，５
−ジフルオロベンゼンのかわりに、４−ブロモ−２−フ
ルオロベンゾトリフルオリド４０．４ｇ（１６７ｍｍｏ
ｌ）を用いる以外は実施例３の第２ステップと同様に反
応を行い、（Ｒ）−２−フルオロ−４−（４−（２−フ
ェニルプロピル）フェニル）ベンゾトリフルオリド［H-
Ph-CH(CH₃)-CH₂-Ph-Ph^F-CF₃］３４．６ｇ（９６．６ｍ
ｍｏｌ）を得た。（収率５８％）ＭＳｍ／ｅ：３５８（Ｍ⁺）Example 4 (R) -2-fluoro-4-
(4- (2-phenylpropyl) phenyl) benzo trifluoride [H-Ph-CH (CH 3) -CH 2 -Ph-Ph F -CF 3]. In the second step of Example 3, 1-bromo-3,5
40.4 g (167 mmol) of 4-bromo-2-fluorobenzotrifluoride instead of difluorobenzene
The reaction was carried out in the same manner as in the second step of Example 3, except that l) was used, to give (R) -2-fluoro-4- (4- (2-phenylpropyl) phenyl) benzotrifluoride [H-
_{Ph-CH (CH 3) -CH} 2 -Ph-Ph F -CF 3] 34.6g (96.6m
mol). (Yield 58%) MS m / e: 358 (M ⁺ )

【００６９】［実施例５］（Ｒ）−２，６−ジフルオロ
−４−（２，６−ジフルオロ−４−（２−フェニルプロ
ピル）フェニル）ベンゾニトリル［H-Ph-CH(CH₃)-CH₂-P
h^FF-Ph ^FF-CN］の合成。＜第１ステップ＞実施例１の第１ステップにおいて、１
−ブロモ−４−クロロベンゼンのかわりに、１−ブロモ
−３，５−ジフルオロベンゼン６４．３ｇ（３３３ｍｍ
ｏｌ）を用いる以外は実施例１の第１ステップと同様に
反応を行い、（Ｓ）−１−（３，５−ジフルオロフェニ
ル）−２−フェニルプロパン−１−オン［H-Ph-CH(CH₃)
-CO-Ph^FF-H］３１．２ｇ（１２７ｍｍｏｌ）を得た。
（収率３８％）ＭＳｍ／ｅ：２４６（Ｍ⁺）Example 5 (R) -2,6-difluoro
-4- (2,6-difluoro-4- (2-phenylpro
Pill) phenyl) benzonitrile [H-Ph-CH (CH_Three) -CH_Two-P
h^FF-Ph ^FF-CN]. <First Step> In the first step of the first embodiment, 1
1-bromo-4-bromo-4-chlorobenzene
64.3 g of -3,5-difluorobenzene (333 mm
ol) in the same manner as in the first step of the first embodiment except that
The reaction is performed and (S) -1- (3,5-difluorophenyl
) -2-phenylpropan-1-one [H-Ph-CH (CH_Three)
-CO-Ph^FF-H] 31.2 g (127 mmol) were obtained.
(Yield 38%) MS m / e: 246 (M⁺)

【００７０】＜第２ステップ＞実施例１の第２ステップ
において、（Ｓ）−１−（４−クロロフェニル）−２−
フェニルプロパン−１−オン［H-Ph-CH(CH₃)-CO-Ph-C
l］のかわりに、第１ステップで合成した（Ｓ）−１−
（３，５−ジフルオロフェニル）−２−フェニルプロパ
ン−１−オン［H-Ph-CH(CH₃)-CO-Ph^FF-H］３１．０ｇ
（１２６ｍｍｏｌ）を用いる以外は実施例１の第１ステ
ップと同様に反応を行い、（Ｒ）−１−（３，５−ジフ
ルオロフェニル）−２−フェニルプロパン［H-Ph-CH(CH
₃)-CH₂-Ph^FF-H］２５．４ｇ（１１０ｍｍｏｌ）を得
た。（収率８７％）ＭＳｍ／ｅ：２３２（Ｍ⁺）<Second Step> In the second step of the first embodiment, (S) -1- (4-chlorophenyl) -2-
Phenylpropan-1-one [H-Ph-CH (CH 3) -CO-Ph-C
l] instead of (S) -1-
(3,5-difluorophenyl) -2-phenyl-propan-1-one [H-Ph-CH (CH 3) -CO-Ph FF -H] 31.0g
(R) -1- (3,5-Difluorophenyl) -2-phenylpropane [H-Ph-CH (CH
₃₎ to obtain a _{^{-CH 2 -Ph FF -H] 25.4g (}} 110mmol). (Yield 87%) MS m / e: 232 (M ⁺ )

【００７１】＜第３ステップ＞３００ｍＬの四ッ口フラ
スコに、第２ステップで得た（Ｒ）−１−（３，５−ジ
フルオロフェニル）−２−フェニルプロパン［H-Ph-CH
(CH₃)-CH₂-Ph^FF-H］１５．０ｇ（６４．６ｍｍｏｌ）、
無水テトラヒドロフラン７５ｍＬを加え、窒素雰囲気下
−７０℃に冷却し、反応温度を−６０℃以下に保ちなが
ら１．５２ｍｏｌ／Ｌｎ−ブチルリチウムヘキサン溶液
５１ｍＬ（７７．５ｍｍｏｌ）を３０分で滴下し、滴下
終了後−７０℃で２時間撹拌した後、−６０℃以下に保
ちながらホウ酸トリメチル８．７２ｇ（１４０ｍｍｏ
ｌ）を無水テトラヒドロフラン１７．４ｍＬに溶解させ
た溶液を３０分で滴下し、滴下終了後室温まで昇温して
室温で一晩撹拌した。<Third Step> The (R) -1- (3,5-difluorophenyl) -2-phenylpropane [H-Ph-CH] obtained in the second step was placed in a 300 mL four-necked flask.
_{_{^{(CH 3) -CH 2 -Ph FF}}} -H] 15.0g (64.6mmol),
75 mL of anhydrous tetrahydrofuran was added, the mixture was cooled to -70 ° C under a nitrogen atmosphere, and while maintaining the reaction temperature at -60 ° C or lower, 51 mL (77.5 mmol) of a 1.52 mol / L n-butyllithium hexane solution was added dropwise over 30 minutes. After completion, the mixture was stirred at −70 ° C. for 2 hours, and then kept at −60 ° C. or lower with 8.72 g (140 mmol) of trimethyl borate.
A solution of l) dissolved in 17.4 mL of anhydrous tetrahydrofuran was added dropwise over 30 minutes, and after completion of the addition, the mixture was heated to room temperature and stirred at room temperature overnight.

【００７２】反応溶液に希塩酸を加え、室温で一時間撹
拌した後に、有機相を分離し、水相をメチル−ｔ−ブチ
ルエーテルで抽出し、有機相とあわせて水、飽和食塩水
で洗浄し、無水硫酸ナトリウムで乾燥し、溶媒を留去し
て（Ｒ）−２，６−ジフルオロ−４−（２−フェニルプ
ロピル）フェニルホウ酸［H-Ph-CH(CH₃)-CH₂-Ph^FF-B(O
H)₂］１４．６ｇ（５３．０ｍｍｏｌ）を得た（収率８
２％）。After adding dilute hydrochloric acid to the reaction solution and stirring at room temperature for 1 hour, the organic phase was separated, the aqueous phase was extracted with methyl-t-butyl ether, and the organic phase was washed with water and saturated saline together with the organic phase. dried over anhydrous sodium sulfate, the solvent was distilled off to (R)-2,6-difluoro-4- (2-phenylpropyl) phenylboronic acid [H-Ph-CH (CH 3) -CH 2 -Ph FF - B (O
H) ₂ ], 14.6 g (53.0 mmol) (yield 8).
2%).

【００７３】＜第４ステップ＞実施例３の第２ステップ
において、（Ｒ）−４−（２−フェニルプロピル）フェ
ニルホウ酸［H-Ph-CH(CH₃)-CH₂-Ph-B(OH)₂］のかわり
に、第３ステップで得た（Ｒ）−２，６−ジフルオロ−
４−（２−フェニルプロピル）フェニルホウ酸［H-Ph-C
H(CH₃)-CH₂-Ph^FF-B(OH)₂］１０．０ｇ（３６．２ｍｍｏ
ｌ）を用いる以外は実施例３の第２ステップと同様に反
応を行い、（Ｒ）−３，５−ジフルオロ−１−（２，６
−ジフルオロ−４−（２−フェニルプロピル）フェニ
ル）ベンゼン［H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^FF-H］６．１
１ｇ（１７．７ｍｍｏｌ）を得た。（収率４９％）ＭＳｍ／ｅ：３４４（Ｍ⁺）<Fourth Step> In the second step of Example 3, (R) -4- (2-phenylpropyl) phenylboric acid [H-Ph-CH (CH ₃ ) -CH ₂ -Ph-B (OH ) ₂ ] instead of the (R) -2,6-difluoro- obtained in the third step.
4- (2-phenylpropyl) phenylboric acid [H-Ph-C
_{_{H (CH 3) -CH 2 -Ph}} FF -B (OH) 2] 10.0g (36.2mmo
The reaction was carried out in the same manner as in the second step of Example 3 except that l) was used, and (R) -3,5-difluoro-1- (2,6)
- difluoro-4- (2-phenylpropyl) phenyl) benzene [H-Ph-CH (CH 3) -CH 2 -Ph FF -Ph FF -H] 6.1
1 g (17.7 mmol) was obtained. (Yield 49%) MS m / e: 344 (M ⁺ )

【００７４】＜第５ステップ＞実施例３の第３ステップ
において、（Ｒ）−３，５−ジフルオロ−１−（４−
（２−フェニルプロピル）フェニル）ベンゼン［H-Ph-C
H(CH₃)-CH₂-Ph-Ph^FF-H］のかわりに、第４ステップで得
た（Ｒ）−３，５−ジフルオロ−１−（２，６−ジフル
オロ−４−（２−フェニルプロピル）フェニル）ベンゼ
ン［H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph^FF-H］６．００ｇ（１
７．４ｍｍｏｌ）を用いる以外は実施例３の第３ステッ
プと同様に反応を行い、（Ｒ）−２，６−ジフルオロ−
４−（２，６−ジフルオロ−４−（２−フェニルプロピ
ル）フェニル）安息香酸［H-Ph-CH(CH ₃)-CH₂-Ph^FF-Ph^FF
-COOH］５．４８ｇ（１４．１ｍｍｏｌ）を得た（収率
８１％）。<Fifth Step> Third Step of Third Embodiment
In the above, (R) -3,5-difluoro-1- (4-
(2-phenylpropyl) phenyl) benzene [H-Ph-C
H (CH_Three) -CH_Two-Ph-Ph^FF-H] instead of the fourth step
(R) -3,5-difluoro-1- (2,6-diflu
Oro-4- (2-phenylpropyl) phenyl) benze
[H-Ph-CH (CH_Three) -CH_Two-Ph^FF-Ph^FF-H] 6.00 g (1
7.4 mmol), except that the third step of Example 3 was used.
(R) -2,6-difluoro-
4- (2,6-difluoro-4- (2-phenylpropyl
Phenyl) benzoic acid [H-Ph-CH (CH _Three) -CH_Two-Ph^FF-Ph^FF
-COOH] 5.48 g (14.1 mmol) was obtained (yield
81%).

【００７５】＜第６ステップ＞実施例３の第４ステップ
において、（Ｒ）−２，６−ジフルオロ−４−（４−
（２−フェニルプロピル）フェニル）安息香酸［H-Ph-C
H(CH₃)-CH₂-Ph-Ph^FF-COOH］のかわりに、第５ステップ
で得たＲ）−２，６−ジフルオロ−４−（２，６−ジフ
ルオロ−４−（２−フェニルプロピル）フェニル）安息
香酸［H-Ph-CH(CH ₃)-CH₂-Ph^FF-Ph^FF-COOH］５．４８ｇ
（１４．１ｍｍｏｌ）を用いる以外は実施例３の第４ス
テップと同様に反応を行い、（Ｒ）−２，６−ジフルオ
ロ−４−（２，６−ジフルオロ−４−（２−フェニルプ
ロピル）フェニル）ベンゾニトリル［H-Ph-CH(CH₃)-CH₂
-Ph^FF-Ph^FF-CN］３．０８ｇ（８．３３ｍｍｏｌ）を得
た（収率５９％）。ＭＳｍ／ｅ：３６９（Ｍ⁺）<Sixth Step> Fourth Step of Third Embodiment
In (R) -2,6-difluoro-4- (4-
(2-Phenylpropyl) phenyl) benzoic acid [H-Ph-C
H (CH_Three) -CH_Two-Ph-Ph^FF-COOH], 5th step
R) -2,6-difluoro-4- (2,6-diph
Fluoro-4- (2-phenylpropyl) phenyl) benzo
Perfluoro acid [H-Ph-CH (CH _Three) -CH_Two-Ph^FF-Ph^FF-COOH] 5.48 g
(44.1 mmol) of Example 3 except that (14.1 mmol) was used.
The reaction was carried out in the same manner as in Tep, and (R) -2,6-difluoro
B-4- (2,6-difluoro-4- (2-phenylp)
Ropyl) phenyl) benzonitrile [H-Ph-CH (CH_Three) -CH_Two
-Ph^FF-Ph^FF-CN] 3.08 g (8.33 mmol) were obtained.
(Yield 59%). MS m / e: 369 (M⁺)

【００７６】［実施例６］（Ｒ）−trans−１−（２，
６−ジフルオロ−４−（２−フェニルプロピル）フェニ
ル）−２−（３−フルオロ−４−トリフルオロメチルフ
ェニル）−１，２−ジフルオロエチレン［H-Ph-CH(CH₃)
-CH₂-Ph^FF-CF=CF-Ph^F-CF₃］の合成。２００ｍＬの四ッ口フラスコに、実施例５の第２ステッ
プで得た（Ｒ）−１−（３，５−ジフルオロフェニル）
−２−フェニルプロパン［H-Ph-CH(CH₃)-CH₂-Ph^FF-H］
１０．０ｇ（４３．１ｍｍｏｌ）、無水テトラヒドロフ
ラン５０ｍＬを加え、窒素雰囲気下−７０℃に冷却し、
反応温度を−６０℃以下に保ちながら１．５２ｍｏｌ／
Ｌｎ−ブチルリチウムヘキサン溶液３４ｍＬ（５１．７
ｍｍｏｌ）を３０分で滴下し、滴下終了後−７０℃で２
時間撹拌した後、−６０℃以下に保ちながら２−フルオ
ロ−４−（１，１，２−トリフルオロビニル）ベンゾト
リフルオリド[CF₂=CF-Ph^F-CF₃]１０．５ｇ（４３．１ｍ
ｍｏｌ）を無水テトラヒドロフラン３１．５ｍＬに溶解
させた溶液を３０分で滴下し、滴下終了後室温まで昇温
して室温で３時間撹拌した。Example 6 (R) -trans-1- (2,2)
6- difluoro-4- (2-phenylpropyl) phenyl) -2- (3-fluoro-4-trifluoromethylphenyl) -1,2-difluoroethylene [H-Ph-CH (CH 3)
-CH ₂ -Ph ^FF -CF = CF-Ph ^F -CF ₃ ]. (R) -1- (3,5-difluorophenyl) obtained in the second step of Example 5 in a 200 mL four-necked flask
2-phenylpropane [H-Ph-CH (CH 3) -CH 2 -Ph FF -H]
10.0 g (43.1 mmol) and 50 mL of anhydrous tetrahydrofuran were added, and the mixture was cooled to -70 ° C under a nitrogen atmosphere.
While maintaining the reaction temperature at −60 ° C. or lower, 1.52 mol /
34 mL of Ln-butyllithium hexane solution (51.7
mmol) in 30 minutes, and 2 drops at −70 ° C.
After stirring time, while maintaining the -60 ° C. or less 2-fluoro-4- (1,1,2-trifluoro vinyl) benzotrifluoride _{^{[CF 2 = CF-Ph F}} -CF 3] 10.5g (43. 1m
mol) was added dropwise over 30 minutes, and after completion of the dropwise addition, the mixture was heated to room temperature and stirred at room temperature for 3 hours.

【００７７】反応溶液に希塩酸を加え、有機相を分離
し、水相をトルエンで抽出し、有機相とあわせて水、炭
酸水素ナトリウム水溶液、飽和食塩水で洗浄し、無水硫
酸マグネシウムで乾燥し、溶媒を留去して粗生成物を得
た。これをシリカゲルカラムクロマトグラフィー（展開
溶媒：ヘキサン）を用いて精製して（Ｒ）−trans−１
−（２，６−ジフルオロ−４−（２−フェニルプロピ
ル）フェニル）−２−（３−フルオロ−４−トリフルオ
ロメチルフェニル）−１，２−ジフルオロエチレン［H-
Ph-CH(CH₃)-CH₂-Ph^FF-CF=CF-Ph^F-CF₃］２．９５ｇ
（６．４６ｍｍｏｌ）を得た。（収率１５％）ＭＳｍ／ｅ：４５６（Ｍ⁺）Dilute hydrochloric acid was added to the reaction solution, the organic phase was separated, the aqueous phase was extracted with toluene, and the combined organic phase was washed with water, an aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain a crude product. This was purified using silica gel column chromatography (developing solvent: hexane) to give (R) -trans-1
-(2,6-difluoro-4- (2-phenylpropyl) phenyl) -2- (3-fluoro-4-trifluoromethylphenyl) -1,2-difluoroethylene [H-
_{Ph-CH (CH 3) -CH} 2 -Ph FF -CF = CF-Ph F -CF 3] 2.95g
(6.46 mmol) was obtained. (Yield 15%) MS m / e: 456 (M ⁺ )

【００７８】［実施例７］（Ｒ）−４−（２，６−ジフ
ルオロ−４−（２−フェニルプロピル）フェニル）フェ
ニル５フッ化硫黄［H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph-SF₅］の
合成。実施例３の第２ステップにおいて、１−ブロモ−３，５
−ジフルオロベンゼンのかわりに、４−ブロモフェニル
５フッ化硫黄[Br-Ph-SF₅]３．０８ｇ（１０．９ｍｍｏ
ｌ）、（Ｒ）−４−（２−フェニルプロピル）フェニル
ホウ酸［H-Ph-CH(CH₃)-CH₂-Ph-B(OH)₂］のかわりに、実
施例５の第３ステップで得た（Ｒ）−２，６−ジフルオ
ロ−４−（２−フェニルプロピル）フェニルホウ酸［H-
Ph-CH(CH ₃)-CH₂-Ph^FF-B(OH)₂］３．００ｇ（１０．９ｍ
ｍｏｌ）を用いる以外は実施例３の第２ステップと同様
に反応を行い、（Ｒ）−４−（２，６−ジフルオロ−４
−（２−フェニルプロピル）フェニル）フェニル５フッ
化硫黄［H-Ph-CH(CH₃)-CH₂-Ph^FF-Ph-SF₅］２．０３ｇ
（４．６７ｍｍｏｌ）を得た。（収率４３％）ＭＳｍ／ｅ：４３４（Ｍ⁺）Example 7 (R) -4- (2,6-diph
Fluoro-4- (2-phenylpropyl) phenyl) fe
Nyl sulfur pentafluoride [H-Ph-CH (CH_Three) -CH_Two-Ph^FF-Ph-SF_Five]of
Synthesis. In the second step of Example 3, 1-bromo-3,5
-Instead of difluorobenzene, 4-bromophenyl
Sulfur pentafluoride [Br-Ph-SF_Five] 3.08g (10.9mmo
1), (R) -4- (2-phenylpropyl) phenyl
Boric acid [H-Ph-CH (CH_Three) -CH_Two-Ph-B (OH)_Two] Instead of
(R) -2,6-difluoro obtained in the third step of Example 5
B-4- (2-Phenylpropyl) phenylboric acid [H-
Ph-CH (CH _Three) -CH_Two-Ph^FF-B (OH)_Two3.00 g (10.9 m
mol)) as in the second step of Example 3 except that
To (R) -4- (2,6-difluoro-4
-(2-phenylpropyl) phenyl) phenyl 5-fluoro
Sulfur chloride [H-Ph-CH (CH_Three) -CH_Two-Ph^FF-Ph-SF_Five] 2.03g
(4.67 mmol) was obtained. (Yield 43%) MS m / e: 434 (M⁺)

【００７９】［液晶組成物の調製例１］メルク社製液晶
組成物ＺＬＩ−１５６５の１００重量部に、実施例１で
合成した（Ｒ）−４−（２−フェニルプロピル）安息香
酸（４−シアノ−３，５−ジフルオロ）フェニル［H-Ph
-CH(CH₃)-CH₂-Ph-COO-Ph^FF-CN：化合物４］を１重量部
（Ｃ＝０．０１）加えた液晶組成物（ア）、実施例２で
合成した（Ｒ）−４−（２−フェニルプロピル）安息香
酸（４−シアノ−３フルオロ）フェニル［H-Ph-CH(CH₃)
-CH₂-Ph-COO-Ph^F-CN：化合物３］を１重量部（Ｃ＝０．
０１）加えた液晶組成物（イ）、実施例３で合成した
（Ｒ）−２，６−ジフルオロ−４−（４−（２−フェニ
ルプロピル）フェニル）ベンゾニトリル［H-Ph-CH(CH₃)
-CH₂-Ph-Ph^FF-CN：化合物２］を１重量部（Ｃ＝０．０
１）加えた液晶組成物（ウ）をそれぞれ得た。[Preparation Example 1 of Liquid Crystal Composition] In 100 parts by weight of a liquid crystal composition ZLI-1565 manufactured by Merck, (R) -4- (2-phenylpropyl) benzoic acid (4-) synthesized in Example 1 was added. Cyano-3,5-difluoro) phenyl [H-Ph
-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^FF -CN: compound 4] (1 part by weight (C = 0.01)) (A), synthesized in Example 2 (R ) -4- (2-phenylpropyl) benzoate (4-cyano-3-fluoro) phenyl [H-Ph-CH (CH 3)
_{^{-CH 2 -Ph-COO-Ph F}} -CN: Compound 3] 1 part by weight (C = 0.
01) The added liquid crystal composition (a), (R) -2,6-difluoro-4- (4- (2-phenylpropyl) phenyl) benzonitrile [H-Ph-CH (CH) synthesized in Example 3 ₃ )
-CH ₂ -Ph-Ph ^FF -CN: compound 2] in an amount of 1 part by weight (C = 0.0
1) The added liquid crystal compositions (c) were obtained.

【００８０】［液晶組成物の比較調製例１］メルク社製
液晶組成物ＺＬＩ−１５６５の１００重量部に市販の光
学活性化合物（ＣＮ）を１重量部（Ｃ＝０．０１）加え
て液晶組成物（エ）、ＺＬＩ−１５６５の１００重量部
に市販のメルク社製光学活性化合物（Ｓ−８１１）を１
重量（Ｃ＝０．０１）部加えて液晶組成物（オ）を得
た。なお、市販の光学活性化合物（ＣＮ）および（Ｓ−
８１１）の構造は３頁に記載した。Comparative Preparation Example 1 of Liquid Crystal Composition To 100 parts by weight of a liquid crystal composition ZLI-1565 manufactured by Merck, 1 part by weight (C = 0.01) of a commercially available optically active compound (CN) was added. (D), 100 parts by weight of ZLI-1565 were mixed with 1 part of a commercially available optically active compound (S-811) manufactured by Merck Ltd.
The liquid crystal composition (E) was obtained by adding the weight (C = 0.01) part. In addition, commercially available optically active compounds (CN) and (S-
The structure of 811) is described on page 3.

【００８１】［らせん誘起力の評価］液晶組成物
（ア）、（イ）、（ウ）、（エ）および（オ）につい
て、２５℃におけるヘリカルピッチ長Ｐ（単位：μｍ）
をカノー（Cano）ウエッジ法にて測定した。計算式１に
よりらせん誘起力ＨＴＰを算出した。また、螺旋誘起の
向きは接触法により測定した。結果を表１に示す。ＨＴＰ＝１／（Ｐ・Ｃ）・・・計算式１[Evaluation of Helical Inducing Force] Helical pitch length P (unit: μm) at 25 ° C. for liquid crystal compositions (A), (A), (C), (D) and (E)
Was measured by the Cano wedge method. The spiral inducing force HTP was calculated by the calculation formula 1. The direction of the spiral induction was measured by a contact method. Table 1 shows the results. HTP = 1 / (PC) Formula 1

【００８２】[0082]

【表１】本発明の化合物（２）、化合物（３）および化合物
（４）のらせん誘起力は、市販の光学活性化合物に比べ
て非常に大きかった。[Table 1] The helix-inducing power of the compound (2), the compound (3) and the compound (4) of the present invention was much larger than that of a commercially available optically active compound.

【００８３】［液晶組成物の調製例２］メルク社製液晶
組成物ＺＬＩ−１５６５の９５モル部に、実施例１で合
成した（Ｒ）−４−（２−フェニルプロピル）安息香酸
（４−シアノ−３，５−ジフルオロ）フェニル［H-Ph-C
H(CH₃)-CH₂-Ph-COO-Ph^FF-CN：化合物４］を５モル部加
えた液晶組成物（カ）、実施例２で合成した（Ｒ）−４
−（２−フェニルプロピル）安息香酸（４−シアノ−３
フルオロ）フェニル［H-Ph-CH(CH₃)-CH₂-Ph-COO-Ph^F-C
N：化合物３］を５モル部加えた液晶組成物（キ）、実
施例３で合成した（Ｒ）−２，６−ジフルオロ−４−
（４−（２−フェニルプロピル）フェニル）ベンゾニト
リル［H-Ph-CH(CH₃)-CH₂-Ph-Ph^FF-CN：化合物２］を５
モル部加えた液晶組成物（ク）をそれぞれ得た。[Preparation Example 2 of Liquid Crystal Composition] In 95 mol parts of the liquid crystal composition ZLI-1565 manufactured by Merck, (R) -4- (2-phenylpropyl) benzoic acid (4-) synthesized in Example 1 was used. Cyano-3,5-difluoro) phenyl [H-Ph-C
H (CH ₃ ) —CH ₂ —Ph—COO—Ph ^FF —CN: compound 4] and 5 mol parts of the liquid crystal composition (f), synthesized in Example 2 (R) -4
-(2-phenylpropyl) benzoic acid (4-cyano-3
Fluoro) phenyl [H-Ph-CH (CH ₃ ) -CH ₂ -Ph-COO-Ph ^F -C
N: Compound 3] (5), and a liquid crystal composition (G) to which (R) -2,6-difluoro-4- synthesized in Example 3 was added.
(4- (2-phenylpropyl) phenyl) benzonitrile [H-Ph-CH (CH ₃ ) -CH ₂ -Ph-Ph ^FF -CN: compound 2]
A liquid crystal composition (h) to which mol parts were added was obtained.

【００８４】［液晶組成物の比較調製例２］メルク社製
液晶組成物ＺＬＩ−１５６５の９５モル部に市販の光学
活性化合物（ＣＢ−１５）を５モル部加えて液晶組成物
（ケ）を得た。なお、市販の光学活性化合物（ＣＢ−１
５）の構造は化５に記載した。[Comparative Preparation Example 2 of Liquid Crystal Composition] To 95 mol parts of the liquid crystal composition ZLI-1565 manufactured by Merck, 5 mol parts of a commercially available optically active compound (CB-15) were added, and the liquid crystal composition (q) was added. Obtained. In addition, a commercially available optically active compound (CB-1
The structure of 5) is described in Chemical formula 5.

【００８５】［誘電率異方性（Δε）の測定］液晶組成
物（カ）、（キ）、（ク）および（ケ）について、Ｎ−
Ｉ転移温度Ｔｃ（Ｋ）を、偏光顕微鏡を用いて測定し
た。結果を表２に示す。[Measurement of Dielectric Anisotropy (Δε)] For the liquid crystal compositions (f), (g), (h) and (h), N-
The I transition temperature Tc (K) was measured using a polarizing microscope. Table 2 shows the results.

【００８６】ＩＴＯ電極付き基盤上に垂直配向処理を施
した基板間に、液晶組成物（カ）、（キ）、（ク）およ
び（ケ）を挟持したセルギャップＤ＝８μｍの液晶セル
を作製した。それぞれのセルについて、ＬＣＲメーター
（ヒューレットパッカード社製４２６３Ｂ）を用いて１
ｋＨｚ、０．８５Ｔｃ（Ｋ）における分子長軸に対して
平行の誘電定数ε_〃を測定した。また、同様に平行配向
処理を施した基板間に液晶組成物（カ）、（キ）、
（ク）および（ケ）を挟持したセルギャップＤ＝８μｍ
の液晶セルを作製し、それぞれのセルについて、ＬＣＲ
メーター（ヒューレットパッカード社製４２６３Ｂ）を
用いて１ｋＨｚ、０．８５Ｔｃ（Ｋ）における分子長軸
に対して垂直の誘電定数ε_⊥を測定した。計算式２によ
り、誘電率異方性（Δε）を算出した。結果を表２に示
す。 Δε＝ε_〃−ε_⊥・・・計算式２A liquid crystal cell having a cell gap D = 8 μm was formed by sandwiching the liquid crystal compositions (f), (g), (h) and (h) between substrates on which a vertical alignment treatment was performed on a substrate with ITO electrodes. did. Using an LCR meter (4263B manufactured by Hewlett-Packard) for each cell, 1
kHz, was measured parallel dielectric constant ε _〃 relative molecular long axis in 0.85Tc (K). In addition, the liquid crystal compositions (f), (g), and
Cell gap D sandwiching (h) and (h) = 8 µm
Were prepared, and the LCR was determined for each cell.
1kHz using a meter (Hewlett Packard 4263B), were measured dielectric constant epsilon _⊥ perpendicular to the molecular long axis in 0.85Tc (K). The dielectric anisotropy (Δε) was calculated by calculation formula 2. Table 2 shows the results. Δε = ε _〃 −ε _⊥ ... Equation 2

【００８７】[0087]

【表２】本発明の化合物（２）、化合物（３）および化合物
（４）を含む液晶組成物（カ）、（キ）および（ク）の
誘電率異方性（Δε）は、市販の光学活性化合物（ＣＢ
−１５）を含む液晶組成物（ケ）に比べて大きかった。
すなわち、本発明の化合物（２）、化合物（３）および
化合物（４）は、市販の光学活性化合物（ＣＢ−１５）
に比べて大きな誘電率異方性（Δε）を示した。[Table 2] The dielectric anisotropy (Δε) of the liquid crystal compositions (f), (g) and (h) containing the compound (2), the compound (3) and the compound (4) of the present invention is determined by using a commercially available optically active compound ( CB
-15) as compared with the liquid crystal composition (q).
That is, compound (2), compound (3) and compound (4) of the present invention are commercially available optically active compound (CB-15)
Showed a large dielectric anisotropy (Δε) as compared with.

【００８８】[0088]

【発明の効果】本発明の光学活性化合物（１）は、らせ
ん誘起力が大きく、ヘリカルピッチ長が短く、かつ誘電
率異方性（Δε）が大きい特性を有する。かかる特性を
有する光学活性化合物（１）を含む液晶組成物は、上記
の従来の液晶組成物に比べて、液晶組成物に少量を添加
することにより所望の配向を達成できるので、該液晶組
成物を用いた液晶素子は、粘度が上昇が小さく、低電圧
での駆動化が可能であり、応答速度が速い。本発明の光
学活性化合物（１）は、特に、ＳＴＮ型またはコレステ
リック型（カイラルネマチック型）液晶表示素子のため
の液晶組成物に有用である。The optically active compound (1) of the present invention has the properties of a large helical inducing force, a short helical pitch length, and a large dielectric anisotropy (Δε). The liquid crystal composition containing the optically active compound (1) having such properties can achieve a desired alignment by adding a small amount to the liquid crystal composition as compared with the above-mentioned conventional liquid crystal composition. The liquid crystal element using the compound has a small increase in viscosity, can be driven at a low voltage, and has a high response speed. The optically active compound (1) of the present invention is particularly useful for a liquid crystal composition for an STN or cholesteric (chiral nematic) liquid crystal display device.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.⁷ 識別記号ＦＩテーマコート゛(参考）Ｃ０９Ｋ 19/14 Ｃ０９Ｋ 19/14 19/20 19/20 19/30 19/30 19/54 19/54 ＢＧ０２Ｆ 1/13 ５００Ｇ０２Ｆ 1/13 ５００ // Ｃ０７Ｍ 7:00 Ｃ０７Ｍ 7:00 (72)発明者大岩正起神奈川県茅ヶ崎市茅ヶ崎三丁目２番10号セイミケミカル株式会社内 (72)発明者橘多聞神奈川県茅ヶ崎市茅ヶ崎三丁目２番10号セイミケミカル株式会社内Ｆターム(参考） 4H006 AA01 AB64 EA22 QN20 QN30 TA04 4H027 BA02 BB04 BD03 BD04 BD08 BD09 BD14 CB04 CB05 CC04 CC05 CE04 CE05 CF04 CF05 CH04 CH05 CJ04 CJ05 CN04 CN05 CP04 CP05 CU04 CU05──────────────────────────────────────────────────続き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C09K 19/14 C09K 19/14 19/20 19/20 19/30 19/30 19/54 19/54 B G02F 1/13 500 G02F 1/13 500 // C07M 7:00 C07M 7:00 (72) Inventor Masaki Oiwa 3-10-10 Chigasaki, Chigasaki City, Kanagawa Prefecture Inside Seimi Chemical Co., Ltd. (72) Inventor Tachibana Tamon 3-2-10, Chigasaki, Chigasaki-shi, Kanagawa F-term (reference) 4H006 AA01 AB64 EA22 QN20 QN30 TA04 4H027 BA02 BB04 BD03 BD04 BD08 BD09 BD14 CB04 CB05 CC04 CC05 CE04 CE05 CF04 CF05 CH04 CN05 C04 CN05 CP04 CP05 CU04 CU05

Claims

[Claims]

1. An optically active compound represented by the following formula (1). Embedded imageHowever, the symbols in the formula (1) have the following meanings, respectively.
Represent. A: CH_Two-Or CO-, B₁, B_Two, B_Three: Independently of one another, -COO-, -OC
O-, -CH_TwoCH_Two-, -CH_TwoO-, -OCH_Two−, −
CF = CF-, -CF_TwoO- or single bond, D₁, D_Two: Independently of each other, unsubstituted 1,4-phenyl
Group, unsubstituted trans-1,4-cyclohexylene group
Or a single bond, X: -CH_Three, -CHF_Two, -CH_TwoF, -CF_ThreeOr
Nitrogen atom, Y₁, Y_Two, Y_Three, Y_Four: Independently of each other, a fluorine atom or
Is a hydrogen atom. Where Y ₁, Y_Two, Y_Three, Y_FourOne of them
Fluorine atom, Z: -CN, -CF_Three, -OCF_Three, -SF_FiveOr
Elemental atom, n: 0 or 1, C^*: Asymmetric carbon atom.

2. An optically active compound represented by the following formula (2). Embedded image

3. An optically active compound represented by the following formula (3). Embedded image

4. An optically active compound represented by the following formula (4). Embedded image

5. A liquid crystal composition comprising the optically active compound according to claim 1.

6. A liquid crystal device using the liquid crystal composition according to claim 5.