JPH10251185A - Optically active compound and liquid crystal composition containing the same - Google Patents

Optically active compound and liquid crystal composition containing the same

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Publication number
JPH10251185A
JPH10251185A JP5645097A JP5645097A JPH10251185A JP H10251185 A JPH10251185 A JP H10251185A JP 5645097 A JP5645097 A JP 5645097A JP 5645097 A JP5645097 A JP 5645097A JP H10251185 A JPH10251185 A JP H10251185A
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JP
Japan
Prior art keywords
formula
group
liquid crystal
compound
optically active
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP5645097A
Other languages
Japanese (ja)
Inventor
Hiroyuki Nohira
博之 野平
Yoshio Aoki
良夫 青木
Osamu Yokokoji
修 横小路
Katsura Isono
桂 磯野
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Seimi Chemical Co Ltd
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Seimi Chemical Co Ltd
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Publication date
Application filed by Seimi Chemical Co Ltd filed Critical Seimi Chemical Co Ltd
Priority to JP5645097A priority Critical patent/JPH10251185A/en
Publication of JPH10251185A publication Critical patent/JPH10251185A/en
Pending legal-status Critical Current

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  • Liquid Crystal Substances (AREA)

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound, having a low viscosity and great helical twistability and useful as a liquid crystal composition. SOLUTION: This compound is represented by the formula R<1> -A<1> -CHX-Y- A<2> -(A<3> )m -R<2> [A<1> is an unsubstituted 1,4-phenylene; A<2> and A<3> are each an unsubstituted 1,4-phenylene, a halogen-substituted 1,4-phenylene, an unsubstituted trans-1,4-cyclohexylene, etc.; R<1> and R<2> are each a 1-10C monovalent aliphatic hydrocarbon, H, a halogen, cyano, etc.; X is CH3 or CF3 ; Y is COO, CH2 COO, CH2 O, etc.; (m) is 0 or 1]. The compound [in which Y is C(CO)O] is obtained by converting an optically active carboxylic acid represented by the formula R<1> -A<1> -CHK-C(O)OH into an acid chloride with thionyl chloride and further reacting the resultant acid chloride with phenols or alcohols. Satisfactory performances are obtained simply by adding a small amount thereof to a liquid crystal composition. Since a liquid crystal electrooptical element using the composition is capable of manifesting high-speed responsiveness and has a low viscosity even at low temperatures, the performances can be maintained even when there is a change in external environment.

Description

【発明の詳細な説明】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
いた液晶電気表示素子に関する。The present invention relates to a novel optically active compound, a liquid crystal composition containing the compound, and a liquid crystal electric display device using the composition.

【０００２】[0002]

【従来の技術】従来、ツイストネマティック（ＴＮ）型
およびスーパーツイストネマティック（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（カイラル剤ともいう）が添加さ
れた液晶組成物が用いられている。これら光学活性物質
としては、従来より光学活性炭素を含む分枝アルキル基
や分枝アルコキシ基を有するカイラルネマティック化合
物、または、コレステリック環を有する化合物が知られ
ている。2. Description of the Related Art Conventionally, twisted nematic (TN) type and super twisted nematic (STN) type liquid crystal display devices are required to achieve uniform twist alignment.
A liquid crystal composition to which a small amount of an optically active compound (also referred to as a chiral agent) is added is used. As these optically active substances, chiral nematic compounds having a branched alkyl group or a branched alkoxy group containing an optically active carbon or compounds having a cholesteric ring have been known.

【０００３】[0003]

【発明が解決しようとする課題】しかし、従来の化合物
はいずれも分子量が大であったり、粘性が高いため、ネ
マティック型液晶表示素子用の組成物に添加した場合に
は、少量添加の場合でもその母体液晶組成物の粘性を増
加させる欠点があった。さらに、液晶組成物の粘性の増
加現象は、光学活性化合物の添加量が多いＳＴＮ型液晶
表示用組成物の場合に、特に顕著となる欠点があった。However, all of the conventional compounds have a large molecular weight or a high viscosity. Therefore, when they are added to a composition for a nematic liquid crystal display element, even if they are added in a small amount, There is a disadvantage that the viscosity of the base liquid crystal composition is increased. Further, the phenomenon of increasing the viscosity of the liquid crystal composition has a drawback that becomes particularly noticeable in the case of an STN-type liquid crystal display composition to which a large amount of an optically active compound is added.

【０００４】また、光学活性物質は、そのピッチ長が長
い化合物であるほど、すなわちカイラルパワーが小さい
化合物であるほど、添加量を多くしなければならないこ
と、液晶組成物の粘性と液晶表示素子の応答性には、正
の相関があることが知られている。以上のことから、液
晶表示素子、特にＳＴＮ型液晶表示素子、の高速応答化
のためには、粘性が小さく、ピッチ長が短い（ショート
ピッチ）光学活性物質が要求されていた。[0004] Further, as the compound having a longer pitch length, that is, a compound having a smaller chiral power, the amount of the optically active substance must be increased, the viscosity of the liquid crystal composition and the viscosity of the liquid crystal display device must be increased. It is known that responsiveness has a positive correlation. From the above, an optically active substance having a small viscosity and a short pitch length (short pitch) has been required for a high-speed response of a liquid crystal display element, particularly an STN type liquid crystal display element.

【０００５】[0005]

【課題を解決するための手段】本発明は、前述の課題を
解決すべくなされたものであり、下式１で表される光学
活性化合物、および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表示素子を提供す
る。 R1-A1-CHX-Y-A2-(A3)m-R2 ・・・式１Means for Solving the Problems The present invention has been made to solve the above-mentioned problems, and has an optically active compound represented by the following formula 1, a liquid crystal composition containing the optically active compound, Provided is a liquid crystal display device using a liquid crystal composition. R 1 -A 1 -CHX-YA 2- (A 3 ) m -R 2 Formula 1

【０００６】ただし、式１中の記号は、以下の意味を示
す。 Ａ1 ：非置換の１，４−フェニレン基。 Ａ2 、Ａ3 ：相互に独立して、非置換の１，４−フェニ
レン基、１個以上のハロゲン原子が置換した１，４−フ
ェニレン基、非置換のトランス−１, ４−シクロヘキシ
レン基、または１個以上のハロゲン原子が置換したトラ
ンス−１, ４−シクロヘキシレン基。However, the symbols in the formula 1 have the following meanings. A 1 : an unsubstituted 1,4-phenylene group. A 2 , A 3 : independently of each other, an unsubstituted 1,4-phenylene group, a 1,4-phenylene group substituted by one or more halogen atoms, an unsubstituted trans-1,4-cyclohexylene group Or a trans-1,4-cyclohexylene group substituted by one or more halogen atoms.

【０００７】Ｒ1 、Ｒ2 ：炭素数１〜１０の１価脂肪族
炭化水素基、炭素数１〜１０のフッ素化１価脂肪族炭化
水素基、水素原子、ハロゲン原子、またはシアノ基であ
り、炭素数１〜１０の１価脂肪族炭化水素基または炭素
数１〜１０のフッ素化１価脂肪族炭化水素基である場合
には、該基中の炭素−炭素結合間にエーテル性の酸素原
子が挿入されていてもよく、該基と、Ａ1 またはＡ3 と
を連結する炭素−炭素結合間にエーテル性の酸素原子が
挿入されていてもよく、該基中の−ＣＨ2 −部分がカル
ボニル基に置換されていてもよい。R 1 and R 2 are a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, a fluorinated monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, a hydrogen atom, a halogen atom, or a cyano group. When it is a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms or a fluorinated monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, etheric oxygen is present between the carbon-carbon bonds in the group. An atom may be inserted, and an etheric oxygen atom may be inserted between a carbon-carbon bond connecting the group to A 1 or A 3, and a —CH 2 — moiety in the group may be inserted. May be substituted with a carbonyl group.

【０００８】Ｘ：−ＣＨ3 または−ＣＦ3 。 Ｙ：−ＣＯＯ−、−ＣＨ2 ＣＯＯ−、−ＣＨ2 Ｏ−、ま
たは−ＣＨ2 ＣＨ2 Ｏ−。 ｍ：０または１。X: -CH 3 or -CF 3 . Y: -COO -, - CH 2 COO -, - CH 2 O-, or -CH 2 CH 2 O-. m: 0 or 1.

【０００９】[0009]

【発明の実施の形態】本発明におけるハロゲン原子とし
ては、塩素原子、臭素原子、フッ素原子が好ましく、特
にフッ素原子が好ましい。BEST MODE FOR CARRYING OUT THE INVENTION As the halogen atom in the present invention, a chlorine atom, a bromine atom and a fluorine atom are preferred, and a fluorine atom is particularly preferred.

【００１０】また、炭素数１〜１０の１価脂肪族炭化水
素基としては、直鎖構造であっても分岐構造であっても
よく、直鎖構造が好ましい。１価脂肪族炭化水素基とし
ては、アルキル基、アルケニル基、またはアルキニル基
が好ましい。炭素数１〜１０のアルキル基としては、具
体例中に記載されるものが挙げられる。The monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms may have a straight-chain structure or a branched structure, and preferably has a straight-chain structure. As the monovalent aliphatic hydrocarbon group, an alkyl group, an alkenyl group, or an alkynyl group is preferable. Examples of the alkyl group having 1 to 10 carbon atoms include those described in the specific examples.

【００１１】炭素数１〜１０のアルケニル基である場合
には、該基中の炭素−炭素２重結合がトランス結合であ
るのが好ましく、特に３−トランス−ペンテニル基また
は３−ブテニル基が好ましい。炭素数１〜１０のアルキ
ニル基である場合の例としては、具体例中に記載するも
のが挙げられる。When it is an alkenyl group having 1 to 10 carbon atoms, the carbon-carbon double bond in the group is preferably a trans bond, particularly preferably a 3-trans-pentenyl group or a 3-butenyl group. . Examples of the alkynyl group having 1 to 10 carbon atoms include those described in the specific examples.

【００１２】また、炭素数１〜１０のフッ素化１価脂肪
族炭化水素基としては、前記の１価脂肪族炭化水素基中
の水素原子の１個以上がフッ素原子に置換された基をい
う。炭素数１〜１０のフッ素化１価脂肪族炭化水素基と
しては、具体例中に記載するものが挙げられる。The fluorinated monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms refers to a group in which at least one hydrogen atom in the above monovalent aliphatic hydrocarbon group has been substituted with a fluorine atom. . Examples of the fluorinated monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms include those described in specific examples.

【００１３】本発明におけるＲ1 およびＲ2 が、それぞ
れ、炭素数１〜１０の１価脂肪族炭化水素基または炭素
数１〜１０のフッ素化１価脂肪族炭化水素基である場合
には、該基中の炭素−炭素結合間、または、該基とＡ1
またはＡ3 （ｍが０である場合には、実質的にはＡ2 ）
とを連結する炭素−炭素結合間にエーテル性の酸素原子
が挿入されていてもよい。例えば、アルコキシアルキル
基、アルコキシ基、フルオロアルコキシ基、（フルオロ
アルコキシ）アルキル基、ペルフルオロ（アルコキシア
ルキル）基等の基が挙げられる。エーテル性の酸素原子
が挿入された基である場合の例としては、具体例中に記
載するものが挙げられる。When R 1 and R 2 in the present invention are each a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms or a fluorinated monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, Between carbon-carbon bonds in the group, or between the group and A 1
Or A 3 (substantially A 2 when m is 0)
And an etheric oxygen atom may be inserted between the carbon-carbon bonds linking Examples include groups such as an alkoxyalkyl group, an alkoxy group, a fluoroalkoxy group, a (fluoroalkoxy) alkyl group, and a perfluoro (alkoxyalkyl) group. Examples of the group in which an etheric oxygen atom is inserted include those described in the specific examples.

【００１４】また、本発明における炭素数１〜１０の１
価脂肪族炭化水素基、または、炭素数１〜１０のフッ素
化１価脂肪族炭化水素基中の−ＣＨ2 −基は、カルボニ
ル基に置換されていてもよい。たとえば、アセチル基、
２，２，２−トリフルオロアセチル基等の基が挙げられ
る。In the present invention, one having 1 to 10 carbon atoms.
The —CH 2 — group in the monovalent aliphatic hydrocarbon group or the fluorinated monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms may be substituted with a carbonyl group. For example, an acetyl group,
And a group such as a 2,2,2-trifluoroacetyl group.

【００１５】また、炭素数１〜１０の１価脂肪族炭化水
素基または炭素数１〜１０のフッ素化１価脂肪族炭化水
素基が分岐構造である場合、これらの基中に不斉炭素原
子を含んでいてもよく、該不斉炭素原子には、フッ素原
子、メチル基、トリフルオロメチル基等が結合している
のが好ましい。When a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms or a fluorinated monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms has a branched structure, an asymmetric carbon atom is contained in these groups. And it is preferable that a fluorine atom, a methyl group, a trifluoromethyl group or the like be bonded to the asymmetric carbon atom.

【００１６】光学活性化合物（式１）におけるＡ2 また
はＡ3 は、非置換の１，４−フェニレン基または１個以
上のハロゲン原子が置換した１，４−フェニレン基が好
ましく、特にＡ2 は非置換の１，４−フェニレン基が好
ましい。[0016] A 2 or A 3 in the optically active compound (formula 1) is an unsubstituted 1,4-phenylene group or one or more 1,4-phenylene group halogen atom-substituted are preferred, especially A 2 Unsubstituted 1,4-phenylene groups are preferred.

【００１７】また、Ａ2 またはＡ3 が１個以上のハロゲ
ン原子が結合した１，４−フェニレン基またはトランス
−１, ４−シクロヘキシレン基である場合、１個以上の
フッ素原子が結合した１，４−フェニレン基または１個
以上のフッ素原子が結合したトランス−１, ４−シクロ
ヘキシレン基が好ましく、特に１または２個のフッ素原
子が結合した１，４−フェニレン基が好ましい。該基と
しては、Ｙの向きにある炭素原子を１位とした場合、３
−フルオロ−１, ４−フェニレン基または３,５−ジフ
ルオロ−１, ４−フェニレン基が好ましい。When A 2 or A 3 is a 1,4-phenylene group or a trans-1,4-cyclohexylene group to which one or more halogen atoms are bonded, a group in which one or more fluorine atoms are bonded. A 1,4-phenylene group or a trans-1,4-cyclohexylene group having one or more fluorine atoms bonded thereto is preferable, and a 1,4-phenylene group having one or two fluorine atoms bonded is particularly preferable. As the group, when the carbon atom in the direction of Y is 1-position, 3
A -fluoro-1,4-phenylene group or a 3,5-difluoro-1,4-phenylene group is preferred.

【００１８】光学活性化合物（式１）におけるＲ1 また
はＲ2 としては、フッ素原子、プロピル基、ペンチル
基、エトキシ基、ｎ−ヘキシルオキシ基、トリフルオロ
メチル基、またはシアノ基が好ましく、特にフッ素原
子、プロピル基、またはｎ−ヘキシルオキシ基が好まし
い。R 1 or R 2 in the optically active compound (formula 1) is preferably a fluorine atom, a propyl group, a pentyl group, an ethoxy group, an n-hexyloxy group, a trifluoromethyl group, or a cyano group. An atom, a propyl group, or an n-hexyloxy group is preferred.

【００１９】また、Ｙは、−ＣＯＯ−、−ＣＨ2 ＣＯＯ
−、−ＣＨ2 Ｏ−、または−ＣＨ2ＣＨ2 Ｏ−を示し、
これらの向きは記載したとおり、すなわち、左側が−Ｃ
ＨＸ−であり、右側がＡ2 である向き、が好ましい。ｍ
は０または１であり、０である場合にはＡ2 とＲ2 とは
直接結合していることを意味する。Y is -COO-, -CH 2 COO
-, - CH 2 O-, or -CH 2 CH 2 O- are shown,
These orientations are as described, ie, the left side is -C
Is HX-, orientation right is A 2, it is preferable. m
Is 0 or 1, and when it is 0, it means that A 2 and R 2 are directly bonded.

【００２０】光学活性化合物（式１）におけるＸが結合
する炭素原子は、不斉炭素原子である。この不斉炭素原
子の絶対配置としてはＳであってもＲであってもよい。
また、本発明の光学活性化合物（式１）は、１種または
２種以上を用いうる。１種を用いる場合には、絶対配置
が１種である化合物を採用するのが好ましい。本発明の
光学活性化合物（式１）の立体構造はラセン構造となっ
ていると考えられ、該化合物（式１）を２種以上採用す
る場合には、このラセンのねじれの向きが同一であるも
のを採用するのが好ましい。The carbon atom to which X is bonded in the optically active compound (formula 1) is an asymmetric carbon atom. The absolute configuration of this asymmetric carbon atom may be S or R.
The optically active compound (Formula 1) of the present invention may be used alone or in combination of two or more. When one kind is used, it is preferable to adopt a compound having one kind of absolute configuration. It is considered that the stereostructure of the optically active compound (formula 1) of the present invention is a helical structure, and when two or more compounds (formula 1) are employed, the twist directions of the helical are the same. It is preferable to employ one.

【００２１】本発明の光学活性化合物（式１）として
は、環の数が２個（ｍが０である場合）の化合物、また
は、環の数が３個（ｍが１である場合）の化合物が存在
しうる。As the optically active compound (formula 1) of the present invention, a compound having two rings (when m is 0) or a compound having three rings (when m is 1) is used. Compounds may be present.

【００２２】まず、環の数が２個の化合物について説明
する。環の数が２個としては、下式２で表される化合物
である。ただし、式２中のＲ1 、Ａ1 、Ｘ、Ｙ、Ａ2 、
Ｒ2 は、式１における意味と同じ意味を示す。 R1-A1-CHX-Y-A2-R2 ・・・式２First, a compound having two rings will be described. The compound having two rings is a compound represented by the following formula 2. Where R 1 , A 1 , X, Y, A 2 ,
R 2 has the same meaning as in Formula 1. R 1 -A 1 -CHX-YA 2 -R 2・ ・ ・ Equation 2

【００２３】式２で表される化合物のうち、本発明にお
いては、Ａ2 が非置換の１，４−フェニレン基または１
個以上のハロゲン原子が置換した１，４−フェニレン基
である場合の式４で表される化合物が好ましい。ただ
し、式４中のＲ1 、Ｘ、Ｙ、Ｒ2 は、式１における意味
と同じ意味を示し、Ｐｈ1 は非置換の１，４−フェニレ
ン基を示し、Ｐｈ2 は、非置換の１，４−フェニレン基
または１個以上のハロゲン原子が置換した１，４−フェ
ニレン基を示す。Ｘ1 はハロゲン原子、ｎは０〜４の整
数を示す。 R1-Ph1-CHX-Y-Ph2-R2 ・・・式４Among the compounds represented by Formula 2, in the present invention, A 2 is an unsubstituted 1,4-phenylene group or
A compound represented by the formula 4 in which at least one halogen atom is a substituted 1,4-phenylene group is preferred. Here, R 1 , X, Y, and R 2 in Formula 4 have the same meanings as in Formula 1, Ph 1 represents an unsubstituted 1,4-phenylene group, and Ph 2 represents an unsubstituted 1-phenylene group. Represents a 1,4-phenylene group or a 1,4-phenylene group substituted by one or more halogen atoms. X 1 represents a halogen atom, and n represents an integer of 0 to 4. R 1 -Ph 1 -CHX-Y-Ph 2 -R 2・ ・ ・ Equation 4

【００２４】[0024]

【化１】 Embedded image

【００２５】式４で表される化合物の具体例としては、
以下に挙げられる。 R1-Ph1-CH(CH3)-C(O)O-Ph2-R2 ・・・式５ R1-Ph1-CH(CH3)-CH2O-Ph2-R2 ・・・式６ R1-Ph1-CH(CH3)-CH2C(O)O-Ph2-R2 ・・・式７ R1-Ph1-CH(CH3)-CH2CH2O-Ph2-R2 ・・・式８ R1-Ph1-CH(CF3)-C(O)O-Ph2-R2 ・・・式９ R1-Ph1-CH(CF3)-CH2O-Ph2-R2 ・・・式１０ R1-Ph1-CH(CF3)-CH2C(O)O-Ph2-R2・・・式１１ R1-Ph1-CH(CF3)-CH2CH2O-Ph2-R2 ・・・式１２Specific examples of the compound represented by Formula 4 include:
These are listed below. R 1 -Ph 1 -CH (CH 3 ) -C (O) O-Ph 2 -R 2・ ・ ・ Formula 5 R 1 -Ph 1 -CH (CH 3 ) -CH 2 O-Ph 2 -R 2・・ ・ Formula 6 R 1 -Ph 1 -CH (CH 3 ) -CH 2 C (O) O-Ph 2 -R 2・ ・ ・ Formula 7 R 1 -Ph 1 -CH (CH 3 ) -CH 2 CH 2 O-Ph 2 -R 2・ ・ ・ Formula 8 R 1 -Ph 1 -CH (CF 3 ) -C (O) O-Ph 2 -R 2・ ・ ・ Formula 9 R 1 -Ph 1 -CH (CF 3 ) -CH 2 O-Ph 2 -R 2 ··· Formula 10 R 1 -Ph 1 -CH (CF 3 ) -CH 2 C (O) O-Ph 2 -R 2 ··· Formula 11 R 1 -Ph 1 -CH (CF 3 ) -CH 2 CH 2 O-Ph 2 -R 2・ ・ ・ Equation 12

【００２６】以下、式５〜１２で表される化合物の具体
例を説明する。以下の具体例においてＰｈは非置換の
１，４−フェニレン基を示し、Ｐｈ（Ｆ）はフッ素原子
が１個置換した１，４−フェニレン基、Ｐｈ（ＦＦ）は
フッ素原子が２個置換した１，４−フェニレン基を示
し、これらのフッ素置換１，４−フェニレン基として
は、３−フルオロ−１, ４−フェニレン基または３, ５
−ジフルオロ−１, ４−フェニレン基が好ましい。Hereinafter, specific examples of the compounds represented by Formulas 5 to 12 will be described. In the following specific examples, Ph represents an unsubstituted 1,4-phenylene group, Ph (F) is a 1,4-phenylene group substituted with one fluorine atom, and Ph (FF) is substituted with two fluorine atoms. A 1,4-phenylene group, and these fluorine-substituted 1,4-phenylene groups include a 3-fluoro-1,4-phenylene group and a 3,5-phenylene group;
-Difluoro-1,4-phenylene groups are preferred.

【００２７】式５で表される化合物の具体例としては、
以下に挙げられる。 H-Ph-CH(CH3)-C(O)O-Ph-H CH3-Ph-CH(CH3)-C(O)O-Ph-CH3 C2H5-Ph-CH(CH3)-C(O)O-Ph-C2H5 C3H7-Ph-CH(CH3)-C(O)O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-C(O)O-Ph-C3H7 CH3O-Ph-CH(CH3)-C(O)O-Ph-C3H7 CH3O-Ph-CH(CH3)-C(O)O-Ph-OC6H13 CH3O-Ph-CH(CH3)-C(O)O-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-C(O)O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-C(O)O-Ph-C≡CCH3 CH3O-Ph-CH(CH3)-C(O)O-Ph-CF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-OCF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-F CH3O-Ph-CH(CH3)-C(O)O-Ph-Cl CH3O-Ph-CH(CH3)-C(O)O-Ph-C≡N CH3O-Ph-CH(CH3)-C(O)O-Ph(F)-F CH3O-Ph-CH(CH3)-C(O)O-Ph(FF)-FSpecific examples of the compound represented by Formula 5 include:
These are listed below. H-Ph-CH (CH 3 ) -C (O) O-Ph-H CH 3 -Ph-CH (CH 3 ) -C (O) O-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3 ) -C (O) O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -C (O) O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph- CH (CH 3 ) -C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH ( CH 3 ) -C (O) O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH ( CH 3 ) -C (O) O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-C≡CCH 3 CH 3 O-Ph- CH (CH 3 ) -C (O) O-Ph-CF 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 )- C (O) O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-F CH 3 O-Ph-CH (CH 3 ) -C (O) O -Ph-Cl CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-C≡N CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph (F)- F CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph (FF) -F

【００２８】式６で表される化合物の具体例としては、
以下に挙げられる。 H-Ph-CH(CH3)-CH2O-Ph-H CH3-Ph-CH(CH3)-CH2O-Ph-CH3 C2H5-Ph-CH(CH3)-CH2O-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2O-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2O-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2O-Ph-C ≡CCH3 CH3O-Ph-CH(CH3)-CH2O-Ph-CF3 CH3O-Ph-CH(CH3)-CH2O-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2O-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2O-Ph-F CH3O-Ph-CH(CH3)-CH2O-Ph-Cl CH3O-Ph-CH(CH3)-CH2O-Ph-C ≡N CH3O-Ph-CH(CH3)-CH2O-Ph(F)-F CH3O-Ph-CH(CH3)-CH2O-Ph(FF)-FSpecific examples of the compound represented by Formula 6 include:
These are listed below. H-Ph-CH (CH 3 ) -CH 2 O-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 O-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3 ) -CH 2 O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3) -CH 2 O-Ph-C 3 H 7 (CH 3) 2 CHCH 2 -Ph-CH (CH 3) -CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-CF 3 CH 3 O-Ph- CH (CH 3 ) -CH 2 O-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-C ≡N CH 3 O-Ph -CH (CH 3 ) -CH 2 O-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph (FF) -F

【００２９】式７で表される化合物の具体例としては、
以下に挙げられる。 H-Ph-CH(CH3)-CH2C(O)O-Ph-H CH3-Ph-CH(CH3)-CH2C(O)O-Ph-CH3 C2H5-Ph-CH(CH3)-CH2C(O)O-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2C(O)O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2C(O)O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-C ≡CCH3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-CF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-F CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Cl CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-C ≡N CH3O-Ph-CH(CH3)-CH2C(O)O-Ph(F)-F CH3O-Ph-CH(CH3)-CH2C(O)O-Ph(FF)-FSpecific examples of the compound represented by the formula 7 include:
These are listed below. H-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-CH 3 C 2 H 5 -Ph -CH (CH 3 ) -CH 2 C (O) O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph- C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O- Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 )- CH 2 C (O) O-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-CF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 C (O) O-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 C (O) O-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 C ( O) O-Ph-C ≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph (FF) -F

【００３０】式８で表される化合物の具体例としては、
以下に挙げられる。 H-Ph-CH(CH3)-CH2CH2O-Ph-H CH3-Ph-CH(CH3)-CH2CH2O-Ph-CH3 C2H5-Ph-CH(CH3)-CH2CH2O-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2CH2O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2CH2O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-C≡CCH3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-CF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-F CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Cl CH3O-Ph-CH(CH3)-CH2CH2O-Ph-C≡N CH3O-Ph-CH(CH3)-CH2CH2O-Ph(F)-F CH3O-Ph-CH(CH3)-CH2CH2O-Ph(FF)-FSpecific examples of the compound represented by Formula 8 include:
These are listed below. H-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph- CH (CH 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH ( CH 3 ) -CH 2 CH 2 O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH ( CH 3 ) -CH 2 CH 2 O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C≡CCH 3 CH 3 O-Ph- CH (CH 3 ) -CH 2 CH 2 O-Ph-CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 CH 2 O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O -Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph (F)- F CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph (FF) -F

【００３１】式９で表される化合物の具体例としては、
以下に挙げられる。 H-Ph-CH(CF3)-C(O)O-Ph-H CH3-Ph-CH(CF3)-C(O)O-Ph-CH3 C2H5-Ph-CH(CF3)-C(O)O-Ph-C2H5 C3H7-Ph-CH(CF3)-C(O)O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-C(O)O-Ph-C3H7 CH3O-Ph-CH(CF3)-C(O)O-Ph-C3H7 CH3O-Ph-CH(CF3)-C(O)O-Ph-OC6H13 CH3O-Ph-CH(CF3)-C(O)O-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-C(O)O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-C(O)O-Ph-C≡CCH3 CH3O-Ph-CH(CF3)-C(O)O-Ph-CF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-OCF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-F CH3O-Ph-CH(CF3)-C(O)O-Ph-Cl CH3O-Ph-CH(CF3)-C(O)O-Ph-C≡N CH3O-Ph-CH(CF3)-C(O)O-Ph(F)-F CH3O-Ph-CH(CF3)-C(O)O-Ph(FF)-FSpecific examples of the compound represented by the formula 9 include:
These are listed below. H-Ph-CH (CF 3 ) -C (O) O-Ph-H CH 3 -Ph-CH (CF 3 ) -C (O) O-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -C (O) O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -C (O) O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph- CH (CF 3 ) -C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH ( CF 3 ) -C (O) O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH ( CF 3 ) -C (O) O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-C≡CCH 3 CH 3 O-Ph- CH (CF 3 ) -C (O) O-Ph-CF 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 )- C (O) O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-F CH 3 O-Ph-CH (CF 3 ) -C (O) O -Ph-Cl CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-C≡N CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph (F)- F CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph (FF) -F

【００３２】式１０で表される化合物の具体例として
は、以下に挙げられる。 H-Ph-CH(CF3)-CH2O-Ph-H CH3-Ph-CH(CF3)-CH2O-Ph-CH3 C2H5-Ph-CH(CF3)-CH2O-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2O-Ph-OC6H13 CH3O-Ph-CH(CF3)-CH2O-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2O-Ph-C ≡CCH3 CH3O-Ph-CH(CF3)-CH2O-Ph-CF3 CH3O-Ph-CH(CF3)-CH2O-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2O-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2O-Ph-F CH3O-Ph-CH(CF3)-CH2O-Ph-Cl CH3O-Ph-CH(CF3)-CH2O-Ph-C ≡N CH3O-Ph-CH(CF3)-CH2O-Ph(F)-F CH3O-Ph-CH(CF3)-CH2O-Ph(FF)-FSpecific examples of the compound represented by the formula 10 are as follows. H-Ph-CH (CF 3 ) -CH 2 O-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 O-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -CH 2 O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3) -CH 2 O-Ph-C 3 H 7 (CH 3) 2 CHCH 2 -Ph-CH (CF 3) -CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-CF 3 CH 3 O-Ph- CH (CF 3 ) -CH 2 O-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-C ≡N CH 3 O-Ph -CH (CF 3 ) -CH 2 O-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph (FF) -F

【００３３】式１１で表される化合物の具体例として
は、以下に挙げられる。 H-Ph-CH(CF3)-CH2C(O)O-Ph-H CH3-Ph-CH(CF3)-CH2C(O)O-Ph-CH3 C2H5-Ph-CH(CF3)-CH2C(O)O-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2C(O)O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2C(O)O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-OC6H13 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-C ≡CCH3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-CF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-F CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Cl CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-C ≡N CH3O-Ph-CH(CF3)-CH2C(O)O-Ph(F)-F CH3O-Ph-CH(CF3)-CH2C(O)O-Ph(FF)-FSpecific examples of the compound represented by the formula 11 are as follows. H-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-CH 3 C 2 H 5 -Ph -CH (CF 3 ) -CH 2 C (O) O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph- C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O- Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 )- CH 2 C (O) O-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-CF 3 CH 3 O-Ph-CH (CF 3 )- CH 2 C (O) O-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 )- CH 2 C (O) O-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 C ( O) O-Ph-C ≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph (FF) -F

【００３４】式１２で表される化合物の具体例として
は、以下に挙げられる。 H-Ph-CH(CF3)-CH2CH2O-Ph-H CH3-Ph-CH(CF3)-CH2CH2O-Ph-CH3 C2H5-Ph-CH(CF3)-CH2CH2O-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2CH2O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2CH2O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-OC6H13 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-C≡CCH3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-CF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-F CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Cl CH3O-Ph-CH(CF3)-CH2CH2O-Ph-C≡N CH3O-Ph-CH(CF3)-CH2CH2O-Ph(F)-F CH3O-Ph-CH(CF3)-CH2CH2O-Ph(FF)-FSpecific examples of the compound represented by the formula 12 are as follows. H-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph- CH (CF 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH ( CF 3 ) -CH 2 CH 2 O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH ( CF 3 ) -CH 2 CH 2 O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-C≡CCH 3 CH 3 O-Ph- CH (CF 3 ) -CH 2 CH 2 O-Ph-CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 )- CH 2 CH 2 O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O -Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-C≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph (F)- F CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph (FF) -F

【００３５】次に、環の数が３個である場合の、本発明
の光学活性化合物について説明する。環の数が３個の化
合物としては下式１３で表される化合物である。ただ
し、式１３中のＲ1 、Ａ1 、Ｘ、Ｙ、Ａ2 、Ａ3 、Ｒ2
は式１における意味と同じ意味を示す。 R1-A1-CHX-Y-A2-A3-R2・・・式１３Next, the optically active compound of the present invention having three rings will be described. The compound having three rings is a compound represented by the following formula 13. Where R 1 , A 1 , X, Y, A 2 , A 3 , R 2
Has the same meaning as in Formula 1. R 1 -A 1 -CHX-YA 2 -A 3 -R 2・ ・ ・ Equation 13

【００３６】式１３で表される化合物は、Ａ2 およびＡ
3 が、それぞれ、非置換の１，４−フェニレン基または
１個以上のハロゲン原子が置換した１，４−フェニレン
基である場合の下式１４で表される化合物が好ましい。
ただし、下式１４において、Ｐｈ1 、Ｐｈ2 、Ｘ1 およ
びｎは、式４における意味と同じ意味を示し、Ｐｈ
3は、非置換の１，４−フェニレン基または１個以上の
ハロゲン原子が置換した１，４−フェニレン基を示す。
Ｘ2 はハロゲン原子、ｋは０〜４の整数を示す。 R1-Ph1-CHX-Y-Ph2-Ph3-R2 ・・・式１４The compound represented by the formula (13) is represented by A 2 and A
When 3 is an unsubstituted 1,4-phenylene group or a 1,4-phenylene group substituted with one or more halogen atoms, a compound represented by the following formula 14 is preferable.
However, in the following formula 14, Ph 1 , Ph 2 , X 1 and n have the same meaning as in the formula 4, and
3 represents an unsubstituted 1,4-phenylene group or a 1,4-phenylene group substituted with one or more halogen atoms.
X 2 represents a halogen atom, and k represents an integer of 0 to 4. R 1 -Ph 1 -CHX-Y-Ph 2 -Ph 3 -R 2・ ・ ・ Equation 14

【００３７】[0037]

【化２】 Embedded image

【００３８】式１４で表される化合物の具体例として
は、以下に挙げられる。 R1-Ph1-CH(CH3)-C(O)O-Ph2-Ph3-R2 ・・・式１５ R1-Ph1-CH(CH3)-CH2O-Ph2-Ph3-R2 ・・・式１６ R1-Ph1-CH(CH3)-CH2-C(O)O-Ph2-Ph3-R2 ・・・式１７ R1-Ph1-CH(CH3)-CH2CH2O-Ph2-Ph3-R2 ・・・式１８ R1-Ph1-CH(CF3)-C(O)O-Ph2-Ph3-R2 ・・・式１９ R1-Ph1-CH(CF3)-CH2O-Ph2-Ph3-R2 ・・・式２０ R1-Ph1-CH(CF3)-CH2-C(O)O-Ph2-Ph3-R2 ・・・式２１ R1-Ph1-CH(CF3)-CH2CH2O-Ph2-Ph3-R2 ・・・式２２Specific examples of the compound represented by the formula 14 are shown below. R 1 -Ph 1 -CH (CH 3 ) -C (O) O-Ph 2 -Ph 3 -R 2・ ・ ・ Formula 15 R 1 -Ph 1 -CH (CH 3 ) -CH 2 O-Ph 2- Ph 3 -R 2・ ・ ・ Formula 16 R 1 -Ph 1 -CH (CH 3 ) -CH 2 -C (O) O-Ph 2 -Ph 3 -R 2・ ・ ・ Formula 17 R 1 -Ph 1- CH (CH 3 ) -CH 2 CH 2 O-Ph 2 -Ph 3 -R 2・ ・ ・ Equation 18 R 1 -Ph 1 -CH (CF 3 ) -C (O) O-Ph 2 -Ph 3 -R 2・ ・ ・ Formula 19 R 1 -Ph 1 -CH (CF 3 ) -CH 2 O-Ph 2 -Ph 3 -R 2・ ・ ・ Formula 20 R 1 -Ph 1 -CH (CF 3 ) -CH 2- C (O) O-Ph 2 -Ph 3 -R 2・ ・ ・ Formula 21 R 1 -Ph 1 -CH (CF 3 ) -CH 2 CH 2 O-Ph 2 -Ph 3 -R 2・ ・ ・ Formula 22

【００３９】以下、式１５〜２２で表される化合物の具
体例を説明する。式１５で表される化合物の具体例とし
ては、以下に挙げられる。 H-Ph-CH(CH3)-C(O)O-Ph-Ph-H CH3-Ph-CH(CH3)-C(O)O-Ph-Ph-CH3 C2H5-Ph-CH(CH3)-C(O)O-Ph-Ph-C2H5 C3H7-Ph-CH(CH3)-C(O)O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-OC6H13 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-C ≡CCH3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-CF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-OCF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-F CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-Cl CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-C ≡N CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph(F)-F CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph(FF)-FHereinafter, specific examples of the compounds represented by Formulas 15 to 22 will be described. Specific examples of the compound represented by Formula 15 include the following. H-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-H CH 3 -Ph-CH (CH 3 ) -C (O) O-Ph-Ph-CH 3 C 2 H 5 -Ph -CH (CH 3 ) -C (O) O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -C (O) O-Ph-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CH 3 ) -C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph- C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph- Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 )- C (O) O-Ph-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CH 3 )- C (O) O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 )- C (O) O-Ph-Ph-F CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-C ≡N CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -C (O ) O-Ph-Ph (FF) -F

【００４０】式１６で表される化合物の具体例として
は、以下に挙げられる。 H-Ph-CH(CH3)-CH2O-Ph-Ph-H CH3-Ph-CH(CH3)-CH2O-Ph-Ph-CH3 C2H5-Ph-CH(CH3)-CH2O-Ph-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-C≡CCH3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-CF3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-F CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-Cl CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-C≡N CH3O-Ph-CH(CH3)-CH2O-Ph-Ph(F)-F CH3O-Ph-CH(CH3)-CH2O-Ph-Ph(FF)-FSpecific examples of the compound represented by Formula 16 are as follows. H-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3) -CH 2 O-Ph- Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3) -CH 2 O-Ph-Ph-C 3 H 7 (CH 3) 2 CHCH 2 -Ph- CH (CH 3 ) -CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH ( CH 3 ) -CH 2 O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH ( CH 3 ) -CH 2 O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-C≡CCH 3 CH 3 O-Ph- CH (CH 3 ) -CH 2 O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph -Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-C≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph (F)- F CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph (FF) -F

【００４１】式１７で表される化合物の具体例として
は、以下に挙げられる。 H-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-H CH3-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-CH3 C2H5-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C≡CCH3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-CF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-F CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-Cl CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C≡N CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph(F)-F CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph(FF)-FThe following are specific examples of the compound represented by the formula (17). H-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-H CH 3 -Ph-CH (CH 3) -CH 2 C (O) O-Ph-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph- Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 )- CH 2 C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-OC 6 H 13 CH 3 O-Ph- CH (CH 3) -CH 2 C (O) O-Ph-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3) -CH 2 C (O) O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-C≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C ( O) O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-C≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph (FF) -F

【００４２】式１８で表される化合物の具体例として
は、以下に挙げられる。 H-Ph-CH(CH3)-CH2CH2O-Ph-Ph-H CH3-Ph-CH(CH3)-CH2CH2O-Ph-Ph-CH3 C2H5-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C ≡CCH3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-CF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-F CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-Cl CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C ≡N CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph(F)-F CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph(FF)-FSpecific examples of the compound represented by the formula 18 are as follows. H-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-CH 3 C 2 H 5 -Ph -CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph- C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph- Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 )- CH 2 CH 2 O-Ph-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 CH 2 O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 CH 2 O-Ph-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-C ≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph (FF) -F

【００４３】式１９で表される化合物の具体例として
は、以下に挙げられる。 H-Ph-CH(CF3)-C(O)O-Ph-Ph-H CH3-Ph-CH(CF3)-C(O)O-Ph-Ph-CH3 C2H5-Ph-CH(CF3)-C(O)O-Ph-Ph-C2H5 C3H7-Ph-CH(CF3)-C(O)O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-OC6H13 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-C ≡CCH3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-CF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-OCF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-F CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-Cl CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-C ≡Ｎ ＣＨ３Ｏ−Ｐｈ−ＣＨ（ＣＦ３）−Ｃ（Ｏ）Ｏ−Ｐｈ−
Ｐｈ（Ｆ）−Ｆ ＣＨ３Ｏ−Ｐｈ−ＣＨ（ＣＦ３）−Ｃ（Ｏ）Ｏ−Ｐｈ−
Ｐｈ（ＦＦ）−ＦSpecific examples of the compound represented by Formula 19 are as follows. H-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-H CH 3 -Ph-CH (CF 3 ) -C (O) O-Ph-Ph-CH 3 C 2 H 5 -Ph -CH (CF 3 ) -C (O) O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -C (O) O-Ph-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CF 3 ) -C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph- C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph- Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 )- C (O) O-Ph-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CF 3 )- C (O) O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 )- C (O) O-Ph-Ph-F CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-C ≡N CH 3 O-Ph-CH (CF 3) -C (O) O-Ph-
Ph (F) -F CH 3 O -Ph-CH (CF 3) -C (O) O-Ph-
Ph (FF) -F

【００４４】式２０で表される化合物の具体例として
は、以下に挙げられる。 Ｈ−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ２Ｏ−Ｐｈ−Ｐｈ−Ｈ ＣＨ３−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ２Ｏ−Ｐｈ−Ｐｈ
−ＣＨ３ Ｃ２Ｈ５−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ２Ｏ−Ｐｈ−Ｐ
ｈ−Ｃ２Ｈ５ Ｃ３Ｈ７−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ２Ｏ−Ｐｈ−Ｐ
ｈ−Ｃ３Ｈ７ （ＣＨ３）２ＣＨＣＨ２−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ
２Ｏ−Ｐｈ−Ｐｈ−Ｃ３Ｈ７ ＣＨ３Ｏ−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ２Ｏ−Ｐｈ−Ｐ
ｈ−Ｃ３Ｈ７ ＣＨ３Ｏ−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ２Ｏ−Ｐｈ−Ｐ
ｈ−ＯＣ６Ｈ１３ ＣＨ３Ｏ−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ２Ｏ−Ｐｈ−Ｐ
ｈ−ＣＨ２ＯＣ２Ｈ５ ＣＨ３Ｏ−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ２Ｏ−Ｐｈ−Ｐ
ｈ−ＣＨ２ＣＨ２ＣＨ＝ＣＨＣＨ３ ＣＨ３Ｏ−Ｐｈ−ＣＨ（ＣＦ３）−ＣＨ２Ｏ−Ｐｈ−Ｐ
ｈ−Ｃ≡CCH3 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-CF3 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-F CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-Cl CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-C≡N CH3O-Ph-CH(CF3)-CH2O-Ph-Ph(F)-F CH3O-Ph-CH(CF3)-CH2O-Ph-Ph(FF)-FSpecific examples of the compound represented by the formula 20 are as follows. H-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-H CH 3 -Ph-CH (CF 3) -CH 2 O-Ph-Ph
-CH 3 C 2 H 5 -Ph- CH (CF 3) -CH 2 O-Ph-P
h-C 2 H 5 C 3 H 7 -Ph-CH (CF 3) -CH 2 O-Ph-P
h-C 3 H 7 (CH 3) 2 CHCH 2 -Ph-CH (CF 3) -CH
2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3) -CH 2 O-Ph-P
h-C 3 H 7 CH 3 O-Ph-CH (CF 3) -CH 2 O-Ph-P
h-OC 6 H 13 CH 3 O-Ph-CH (CF 3) -CH 2 O-Ph-P
h-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3) -CH 2 O-Ph-P
h-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3) -CH 2 O-Ph-P
h-C≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-F CH 3 O-Ph -CH (CF 3 ) -CH 2 O-Ph-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-C≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph (FF) -F

【００４５】式２１で表される化合物の具体例として
は、以下に挙げられる。 H-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-H CH3-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-CH3 C2H5-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-OC6H13 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C≡CCH3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-CF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-F CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-Cl CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C≡N CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph(F)-F CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph(FF)-FSpecific examples of the compound represented by the formula 21 are as follows. H-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph- Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 )- CH 2 C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-OC 6 H 13 CH 3 O-Ph- CH (CF 3) -CH 2 C (O) O-Ph-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3) -CH 2 C (O) O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-C≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C ( O) O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-C≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph (FF) -F

【００４６】式２２で表される化合物の具体例として
は、以下に挙げられる。 H-Ph-CH(CF3)-CH2CH2O-Ph-Ph-H CH3-Ph-CH(CF3)-CH2CH2O-Ph-Ph-CH3 C2H5-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-OC6H13 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C ≡CCH3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-CF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-F CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-Cl CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C ≡N CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph(F)-F CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph(FF)-FSpecific examples of the compound represented by the formula 22 are shown below. H-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-CH 3 C 2 H 5 -Ph -CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph- C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph- Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 )- CH 2 CH 2 O-Ph-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CF 3 )- CH 2 CH 2 O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 )- CH 2 CH 2 O-Ph-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C ≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph (FF) -F

【００４７】本発明における光学活性化合物（式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。The optically active compound (formula 1) in the present invention is a novel compound and can be produced, for example, according to the following method.

【００４８】［方法１］Ｙが−Ｃ（Ｏ）Ｏ−である場合 [Method 1] When Y is -C (O) O-

【００４９】方法１は、光学活性カルボン酸（式Ａ）を
塩化チオニルで酸クロリド化し、さらにフェノール類ま
たはアルコール類（式Ｃ）と反応させて目的化合物を得
る方法である。光学活性カルボン酸化合物（式Ａ）の酸
クロリド化反応、および、光学活性酸クロリド化合物
（式Ｂ）とフェノール類またはアルコール類（式Ｃ）と
の反応において、それぞれ式中の不斉炭素原子の絶対配
置は保持される。Method 1 is a method in which an optically active carboxylic acid (formula A) is acid chlorided with thionyl chloride and further reacted with phenols or alcohols (formula C) to obtain a target compound. In the acid chloride reaction of the optically active carboxylic acid compound (formula A) and the reaction of the optically active acid chloride compound (formula B) with phenols or alcohols (formula C), each of the asymmetric carbon atoms in the formula Absolute configuration is preserved.

【００５０】［方法２］Ｙが−ＣＨ2 Ｏ−である場合 [Method 2] When Y is —CH 2 O—

【００５１】方法２は、光学活性カルボン酸（式Ａ）を
ＬｉＡｌＨ4 にて還元して光学活性アルコール誘導体
（式Ｄ）とし、次にこれを塩化パラトルエンスルホニル
によってトシル化（Ｔｓはトシル基を示す。）し、これ
とフェノール類またはアルコール類（式Ｃ）と反応させ
目的化合物を得る方法である。光学活性カルボン酸化合
物（式Ａ）の還元反応および光学活性アルコール化合物
（式Ｄ）のトシル化反応および光学活性トシレート化合
物（式Ｅ）とフェノール類またはアルコール類（式Ｄ）
との反応において、それぞれ式中の不斉炭素原子の絶対
配置は保持される。In the method 2, the optically active carboxylic acid (formula A) is reduced with LiAlH 4 to obtain an optically active alcohol derivative (formula D), which is then tosylated with paratoluenesulfonyl chloride (Ts is a tosyl group). This is a method of reacting this with phenols or alcohols (formula C) to obtain the desired compound. Reduction reaction of optically active carboxylic acid compound (formula A) and tosylation reaction of optically active alcohol compound (formula D) and optically active tosylate compound (formula E) with phenols or alcohols (formula D)
In each reaction, the absolute configuration of the asymmetric carbon atom in the formula is retained.

【００５２】［方法３］Ｙが−ＣＨ2 Ｃ（Ｏ）Ｏ−であ
る場合 [Method 3] When Y is —CH 2 C (O) O—

【００５３】方法３は、光学活性カルボン酸（式Ｆ）を
塩化チオニルで酸クロリド化し、さらにフェノール類ま
たはアルコール類（式Ｃ）と反応させ目的化合物を得る
方法である。光学活性カルボン酸（式Ｆ）の酸クロリド
化反応および光学活性酸クロリド化合物（式Ｇ）とフェ
ノール類またはアルコール類（式Ｃ）との反応におい
て、それぞれ式中の不斉炭素原子の絶対配置は保持され
る。Method 3 is a method in which an optically active carboxylic acid (formula F) is acid chlorided with thionyl chloride and further reacted with a phenol or alcohol (formula C) to obtain a target compound. In the acid chloride reaction of the optically active carboxylic acid (formula F) and the reaction of the optically active acid chloride compound (formula G) with phenols or alcohols (formula C), the absolute configuration of the asymmetric carbon atom in each formula is Will be retained.

【００５４】［方法４］Ｙが−ＣＨ2 ＣＨ2 Ｏ−である
場合 [Method 4] When Y is —CH 2 CH 2 O—

【００５５】方法４は、光学活性カルボン酸をＬｉＡｌ
Ｈ4 （式Ｆ）にて還元して光学活性アルコール誘導体
（式Ｈ）とし、次にこれを塩化パラトルエンスルホニル
によってトシル化し、これとフェノール類またはアルコ
ール類（式Ｃ）と反応させ目的化合物を得る方法であ
る。光学活性カルボン酸化合物（式Ｆ）の還元反応およ
び光学活性アルコール化合物（式Ｈ）のトシル化反応お
よび光学活性トシレート化合物（式Ｉ）とフェノール類
またはアルコール類（式Ｃ）との反応において、それぞ
れ式中の不斉炭素原子の絶対配置は保持される。In the method 4, the optically active carboxylic acid is converted to LiAl
The compound is reduced with H 4 (Formula F) to give an optically active alcohol derivative (Formula H), which is then tosylated with paratoluenesulfonyl chloride and reacted with phenols or alcohols (Formula C) to give the desired compound. How to get. In the reduction reaction of the optically active carboxylic acid compound (formula F), the tosylation reaction of the optically active alcohol compound (formula H), and the reaction of the optically active tosylate compound (formula I) with a phenol or alcohol (formula C), respectively. The absolute configuration of the asymmetric carbon atom in the formula is retained.

【００５６】上記の方法１〜４の原料化合物である式Ａ
または式Ｆで表される化合物は、いずれも公知の化合物
である。上記の方法は、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
（式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 compound of formula A, which is the starting compound of the above methods 1-4,
Alternatively, all the compounds represented by the formula F are known compounds. Since any of the above methods can maintain the absolute configuration of the raw material, the raw material compound may be appropriately changed according to the absolute configuration of the target optically active compound (formula 1).

【００５７】本発明の光学活性化合物（式１）は、１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
記す。）に含ませて液晶組成物とするのが好ましい。本
発明の光学活性化合物を含む液晶組成物は、低粘性であ
り、かつ、該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
成できる。The optically active compound (formula 1) of the present invention comprises one or more kinds of other liquid crystal materials and / or non-liquid crystal materials (hereinafter, referred to as “liquid crystal materials”).
Other liquid crystal materials and non-liquid crystal materials are collectively referred to as “other materials”. ) To form a liquid crystal composition. The liquid crystal composition containing the optically active compound of the present invention has low viscosity, and when a TN or STN liquid crystal display device is formed using the liquid crystal composition, uniform twist alignment can be achieved.

【００５８】他の材料中に光学活性化合物（式１）を含
ませて液晶組成物とする場合には、光学活性化合物（式
１）の量は、他の材料の１００重量部中に対して０．１
〜１０重量部が好ましく、特に０．５〜３重量部が好ま
しい。When a liquid crystal composition is prepared by incorporating an optically active compound (formula 1) into another material, the amount of the optically active compound (formula 1) is based on 100 parts by weight of the other material. 0.1
It is preferably from 10 to 10 parts by weight, particularly preferably from 0.5 to 3 parts by weight.

【００５９】他の材料としては、以下の化合物が例示で
きる。なお、下式におけるＲC 、ＲD 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は置換されていてもよいト
ランス−１，４−ヘキシレン基、Ｐｈ4 は非置換または
置換された１，４−フェニレン基を示す。The following compounds can be exemplified as other materials. In the following formula, R C and R D are each independently of one another, an alkyl group, an alkoxy group, a halogen atom,
Or Cy represents a cyano group, Cy represents an optionally substituted trans-1,4-hexylene group, and Ph 4 represents an unsubstituted or substituted 1,4-phenylene group.

【００６０】RC-Cy-Cy-RD RC-Cy-Ph4-RD RC-Ph4-Ph4-RD RC-Cy-COO-Ph4-RD RC-Ph4-COO-Ph4-RD RC-Ph4-C≡C-Ph4-RD RC-Cy-CH2CH2-Ph4-C≡C-Ph4-RD RC-Cy-CH2CH2-Ph4-RD RC-Ph4-CH2CH2-Ph4-RD RC-Cy-Cy-Ph4-RD RC-Cy-Ph4-Ph4-RD RC-Cy-Ph4-Ph4-Cy-RD RC-Ph4-Ph4-Ph4-RD RC-Cy-COO-Ph4-Ph4-RD RC-Cy-Ph4-COO-Ph4-RD RC-Cy-COO-Ph4-COO-Ph4-RD RC-Ph4-COO-Ph4-COO-Ph4-RD RC-Ph4-COO-Ph4-OCO-Ph4-RD R C -Cy-Cy-R D R C -Cy-Ph 4 -R D R C -Ph 4 -Ph 4 -R D R C -Cy-COO-Ph 4 -R D R C -Ph 4 -COO-Ph 4 -R D R C -Ph 4 -C≡C-Ph 4 -R D R C -Cy-CH 2 CH 2 -Ph 4 -C≡C-Ph 4 -R D R C -Cy- CH 2 CH 2 -Ph 4 -R D R C -Ph 4 -CH 2 CH 2 -Ph 4 -R D R C -Cy-Cy-Ph 4 -R D R C -Cy-Ph 4 -Ph 4 -R D R C -Cy-Ph 4 -Ph 4 -Cy-R D R C -Ph 4 -Ph 4 -Ph 4 -R D R C -Cy-COO-Ph 4 -Ph 4 -R D R C -Cy- Ph 4 -COO-Ph 4 -R D R C -Cy-COO-Ph 4 -COO-Ph 4 -R D R C -Ph 4 -COO-Ph 4 -COO-Ph 4 -R D R C -Ph 4 -COO-Ph 4 -OCO-Ph 4 -R D

【００６１】他の材料として挙げた上記化合物は単なる
例示であり、該化合物の環構造を、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
キサン環等の他の五員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-mentioned compounds listed as other materials are merely examples, and the ring structure of the compound is changed to another six-membered ring such as a cyclohexane ring or a benzene ring, or another five-membered ring such as a pyridine ring or a dioxane ring. May be substituted, the terminal hydrogen atom of the compound may be substituted with a halogen atom, a cyano group, a methyl group, or the like, or the bonding group between rings may be changed to another bonding group. Good. These can be appropriately changed according to desired performance.

【００６２】本発明の化合物を含む液晶組成物は、液晶
セルに注入する等の方法で、電極付の基板間に挟持し
て、液晶電気光学素子を構成する。代表的な液晶セルと
しては、ＴＮ型液晶電気光学素子がある。なお、本発明
の液晶電気光学素子は、調光窓、光シャッタ、偏光交換
素子等の表示用途以外にも使用できる。液晶電気光学素
子は、ＴＮ方式、ＳＴＮ方式、ゲスト・ホスト（ＧＨ）
方式、動的散乱方式、フェーズチェンジ方式、ＤＡＰ方
式、二周波駆動方式、強誘電性液晶表示方式等の種々の
方式で使用できる。The liquid crystal composition containing the compound of the present invention is sandwiched between substrates having electrodes by a method such as injection into a liquid crystal cell to constitute a liquid crystal electro-optical element. A typical liquid crystal cell is a TN type liquid crystal electro-optical element. The liquid crystal electro-optical element of the present invention can be used for purposes other than display such as a light control window, an optical shutter, and a polarization exchange element. Liquid crystal electro-optic device is TN type, STN type, guest host (GH)
It can be used in various systems such as a system, a dynamic scattering system, a phase change system, a DAP system, a dual frequency driving system, and a ferroelectric liquid crystal display system.

【００６３】液晶電気光学素子の製法としては、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 、Ａｌ
2 Ｏ3 等のアンダーコート層やカラーフィルタ層を形成
し、Ｉｎ2 Ｏ3 −ＳｎＯ2 （ＩＴＯ）、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。As a method of manufacturing a liquid crystal electro-optical element, the following method can be basically used. That is, if necessary, SiO 2 , Al
After forming an undercoat layer such as 2 O 3 and a color filter layer, providing electrodes such as In 2 O 3 —SnO 2 (ITO) and SnO 2 and patterning, if necessary, polyimide, polyamide, SiO 2 , An overcoat layer of Al 2 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.
The sealing material is cured to form empty cells.

【００６４】この空セルに、本発明の液晶組成物を注入
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、ノングレア加工するなどして液晶電気光学素子
が製造される。The liquid crystal composition of the present invention is injected into the empty cell, and the injection port is sealed with a sealant to form a liquid crystal cell. If necessary, a polarizing plate, a color polarizing plate, a light source, a color filter, a transflective reflector, a reflector, a light guide plate,
A liquid crystal electro-optical element is manufactured by laminating an ultraviolet cut filter or the like, printing characters, figures, or the like, or performing non-glare processing.

【００６５】さらに、液晶電気光学素子としては、２層
電極を用いた基板、２層の液晶層を形成した２層液晶セ
ル、ＴＦＴ、ＭＩＭ等の能動素子を形成したアクティブ
マトリクス基板を用いたアクティブマトリクス素子等の
種々の構成のものが使用できる。Further, as the liquid crystal electro-optical element, an active substrate using a substrate using two-layer electrodes, a two-layer liquid crystal cell having two liquid crystal layers formed thereon, and an active matrix substrate having active elements such as TFTs and MIMs formed thereon. Various components such as a matrix element can be used.

【００６６】本発明の光学活性化合物（式１）は、液晶
組成物中に少量を添加することにより、粘性を大きく増
大させることなく、液晶に大きなねじれ配向を誘起させ
ることができる。このため、近年注目されている高ツイ
スト角のスーパーツイスト（ＳＴＮ）型液晶電気光学素
子に好適である。その他、多色性色素を用いたＧＨ型液
晶表示素子、強誘電性液晶電気光学素子等にも使用でき
る。By adding a small amount of the optically active compound (formula 1) of the present invention to a liquid crystal composition, a large twist alignment can be induced in the liquid crystal without greatly increasing the viscosity. Therefore, it is suitable for a super twist (STN) type liquid crystal electro-optical element having a high twist angle, which has attracted attention in recent years. In addition, it can be used for a GH type liquid crystal display device using a polychromatic dye, a ferroelectric liquid crystal electro-optical device, and the like.

【００６７】[0067]

【実施例】【Example】

［実施例１］ ［第１ステップ］(S)-(-)-2-フェニル-1- プロパノール
の合成 水素化リチウムアルミニウム205mg(5.40mmol) をジエチ
ルエーテル1.5ml 中でおよそ２０分間水冷撹拌した。次
いで水冷しながら(S)-(+)-2-フェニルプロピオン酸401m
g(2.67mmol) をジエチルエーテル5ml に溶解させたもの
を滴下漏斗より１０分間かけて滴下し、滴下漏斗の壁面
を少量のジエチルエーテルで洗い流した。滴下後１０分
間室温で撹拌させた後、４０℃の油浴で３時間加熱撹拌
した。反応後室温まで冷却させた後、ジエチルエーテル
を加え、激しく撹拌させながら硫酸ナトリウム飽和水溶
液をゲルが生成するまで滴下した。エーテル層を傾斜法
で分取しゲルを少量のエーテルで洗浄した。エーテル層
を硫酸ナトリウムで一晩乾燥させ、乾燥剤を除去し、溶
媒を減圧留去し、365mg の粗体を得た。これを減圧留去
することにより無色透明の液体の(S)-(-)-2-フェニル-1
- プロパノールを307mg(2.26mmol) 得た。収率は84.7%
であった。 H-Ph-CH(CH3)-CH2OH 比旋光度：［α］D 26=−7.65°(c=5, MeOH)[Example 1] [First step] Synthesis of (S)-(-)-2-phenyl-1-propanol 205 mg (5.40 mmol) of lithium aluminum hydride was stirred in 1.5 ml of diethyl ether with water cooling for about 20 minutes. Then while cooling with water (S)-(+)-2-phenylpropionic acid 401m
g (2.67 mmol) dissolved in 5 ml of diethyl ether was added dropwise from a dropping funnel over 10 minutes, and the wall of the dropping funnel was washed away with a small amount of diethyl ether. After the addition, the mixture was stirred at room temperature for 10 minutes and then heated and stirred in a 40 ° C. oil bath for 3 hours. After cooling to room temperature after the reaction, diethyl ether was added, and a saturated aqueous solution of sodium sulfate was added dropwise with vigorous stirring until a gel was formed. The ether layer was separated by a gradient method, and the gel was washed with a small amount of ether. The ether layer was dried over sodium sulfate overnight to remove the desiccant, and the solvent was distilled off under reduced pressure to obtain 365 mg of a crude product. This was distilled off under reduced pressure to give a colorless and transparent liquid (S)-(-)-2-phenyl-1.
-307 mg (2.26 mmol) of propanol were obtained. 84.7% yield
Met. H-Ph-CH (CH 3 ) -CH 2 OH Specific rotation: [α] D 26 = −7.65 ° (c = 5, MeOH)

【００６８】［第２ステップ］(S)-p-トルエンスルホン
酸 2- フェニル-1- プロピルの合成 塩化-p- トルエンスルホニル415mg(2.18mmol) を乾燥ジ
クロロメタンに溶解した。そこへ(S)-(-)-2-フェニル-1
- プロパノール296mg(2.18mmol) を乾燥ジクロロメタン
1.5ml で流し込み、その直後に1,4-ジアザビシクロ[2.
2.2］オクタン（ＤＡＢＣＯ）268mg(2.39mmol) を乾燥
ジクロロメタン1.5ml で流し込んだ。一晩室温で撹拌し
た後、ジエチルエーテルを加え有機層を飽和食塩水、希
塩酸、炭酸水素ナトリウム飽和水溶液で洗浄した。有機
層を無水硫酸ナトリウムで一晩かけて乾燥し、乾燥剤を
除去した後、溶媒を減圧留去し445mg の白色の粗体を得
た。これを薄層クロマトグラフィ（展開溶媒はベンゼ
ン）で精製し、白色個体の(S)-p-トルエンスルホン酸 2
- フェニル-1- プロピルを406mg(1.40mmol) 得た。収率
は64.3% であった。 H-Ph-CH(CH3)-CH2OTs[Second Step] Synthesis of 2-phenyl-1-propyl (S) -p-toluenesulfonate 415 mg (2.18 mmol) of p-toluenesulfonyl chloride was dissolved in dry dichloromethane. There (S)-(-)-2-phenyl-1
-296 mg (2.18 mmol) of propanol in dry dichloromethane
Pour in 1.5 ml and immediately afterwards, 1,4-diazabicyclo [2.
2.2] 268 mg (2.39 mmol) of octane (DABCO) were poured in with 1.5 ml of dry dichloromethane. After stirring overnight at room temperature, diethyl ether was added and the organic layer was washed with saturated saline, diluted hydrochloric acid, and a saturated aqueous solution of sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate overnight to remove the desiccant, and the solvent was distilled off under reduced pressure to obtain 445 mg of a white crude product. This is purified by thin-layer chromatography (developing solvent is benzene), and (S) -p-toluenesulfonic acid 2
-Phenyl-1-propyl (406 mg, 1.40 mmol) was obtained. The yield was 64.3%. H-Ph-CH (CH 3 ) -CH 2 OTs

【００６９】［第３ステップ］(S)-(+)-2-フェニル-1-
プロピル-4- ヘキシルオキシフェニルエーテルの合成 炭酸カリウム393mg(2.85mmol) を2-ブタノン1ml に加え
撹拌させた。そこへ4-ヘキシルオキシフェノール276mg
(1.42mmol) を2-ブタノン1ml で流し込んだ。白濁溶液
へさらに(S)-p-トルエンスルホン酸 2- フェニル-1- プ
ロピル276mg(1.40mmol) を2-ブタノン1ml で流し込み、
90℃で６０時間加熱還流させた。反応後イオン交換水に
溶解しジエチルエーテルで抽出した。有機層を１規定水
酸化ナトリウム溶液、イオン交換水で洗浄した。有機層
を無水硫酸ナトリウムで一晩かけて乾燥させた。乾燥剤
を除去した後、溶媒を減圧留去し、479mg の白色の粗体
を得た。これを薄層クロマトグラフィ（展開溶媒はヘキ
サン１０に対し酢酸エチル１の混合溶媒を用いた）で精
製し、無色の液体の(S)-(+)-2-フェニル-1- プロピル-4
- ヘキシルオキシフェニルエーテルを216mg(0.69mmol)
得た。収率は49.4% であった。[Third Step] (S)-(+)-2-phenyl-1-
Synthesis of propyl-4-hexyloxyphenyl ether 393 mg (2.85 mmol) of potassium carbonate was added to 1 ml of 2-butanone and stirred. There 276mg 4-hexyloxyphenol
(1.42 mmol) was poured in with 1 ml of 2-butanone. 276 mg (1.40 mmol) of 2-phenyl-1-propyl (S) -p-toluenesulfonate was further poured into the cloudy solution with 1 ml of 2-butanone,
The mixture was heated and refluxed at 90 ° C. for 60 hours. After the reaction, the product was dissolved in ion-exchanged water and extracted with diethyl ether. The organic layer was washed with a 1N sodium hydroxide solution and ion-exchanged water. The organic layer was dried over anhydrous sodium sulfate overnight. After removing the desiccant, the solvent was distilled off under reduced pressure to obtain 479 mg of a white crude product. This was purified by thin-layer chromatography (developing solvent using a mixed solvent of 10 hexanes and 1 ethyl acetate) to give a colorless liquid (S)-(+)-2-phenyl-1-propyl-4
-216 mg (0.69 mmol) of hexyloxyphenyl ether
Obtained. The yield was 49.4%.

【００７０】得られた化合物のガスクロマトグラフ・質
量分析（ＧＣ−Ｍａｓｓ）結果を図１に、1 Ｈ−ＮＭＲ
スペクトル（溶媒：ＣＤＣｌ3 、基準物質：ＴＭＳ）を
図２に、13Ｃ−ＮＭＲスペクトル（溶媒：ＣＤＣｌ3 、
基準物質：ＴＭＳ）を図３に、ＩＲスペクトル（ＫＢｒ
法）を図４に示す。 H-Ph-CH(CH3)-CH2O-Ph-OC6H13 ・・・式２３ 比旋光度：［α］D 27=−11.1°(c=0.5, CHCl3)，［α］
435 24 ＝−21.5°(c=0.5, CHCl3)．[0070] Gas chromatograph mass analysis of the obtained compound (GC-Mass) results in FIG. 1, 1 H-NMR
The spectrum (solvent: CDCl 3 , reference substance: TMS) is shown in FIG. 2 and the 13 C-NMR spectrum (solvent: CDCl 3 ,
FIG. 3 shows the IR spectrum (KBr) of the reference substance: TMS.
Method) is shown in FIG. H-Ph-CH (CH 3 ) -CH 2 O-Ph-OC 6 H 13 Formula 23 Specific rotation: [α] D 27 = −11.1 ° (c = 0.5, CHCl 3 ), [α]
435 24 = -21.5 ° (c = 0.5, CHCl 3 ).

【００７１】[0071]

【化３】 Embedded image

【００７２】実施例１と同様にして、以下の化合物を得
ることができる。なお、下記化合物中の不斉炭素の絶対
配置は、Ｓ体のカルボン酸を用いた場合はＳであり、Ｒ
体のカルボン酸を用いた場合はＲである。また、下記化
合物中のアルキル基部分は、直鎖構造であることを意味
する。以下の実施例についても同様である。The following compounds can be obtained in the same manner as in Example 1. Incidentally, the absolute configuration of the asymmetric carbon in the following compound is S when a carboxylic acid of S form is used, and R
R when a carboxylic acid in a form is used. Further, the alkyl group portion in the following compound means a straight-chain structure. The same applies to the following embodiments.

【００７３】H-Ph-CH(CH3)-CH2O-Ph-H CH3-Ph-CH(CH3)-CH2O-Ph-CH3 C2H5-Ph-CH(CH3)-CH2O-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2O-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2O-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2O-Ph-C ≡CCH3 CH3O-Ph-CH(CH3)-CH2O-Ph-CF3 CH3O-Ph-CH(CH3)-CH2O-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2O-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2O-Ph-F CH3O-Ph-CH(CH3)-CH2O-Ph-Cl CH3O-Ph-CH(CH3)-CH2O-Ph-C ≡N CH3O-Ph-CH(CH3)-CH2O-Ph(F)-F CH3O-Ph-CH(CH3)-CH2O-Ph(FF)-FH-Ph-CH (CH 3 ) -CH 2 O-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 O-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3 ) -CH 2 O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -CH 2 O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CH 3 ) -CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph -OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-CF 3 CH 3 O -Ph-CH (CH 3 ) -CH 2 O-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-C ≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph (FF) -F

【００７４】［実施例２］実施例１の第３ステップにお
いて、4-ヘキシルオキシフェノールのかわりに、4-（4-
プロピルフェニル）フェノールを 301mg(1.42mmol)用い
る以外は実施例１と同様に反応を行い、(S)-2-フェニル
-1- プロピル-(4'- プロピルビフェニル-4- イル）エー
テルを214mg(0.65mmol) 得た。収率は46% であった。マ
ススペクトルの測定結果を記す。 H-Ph-CH(CH3)-CH2O-Ph-Ph-C3H7 ＭＳ m/e 330(M+)Example 2 In the third step of Example 1, 4- (4-
The reaction was carried out in the same manner as in Example 1 except that 301 mg (1.42 mmol) of propylphenyl) phenol was used.
214 mg (0.65 mmol) of -1-propyl- (4′-propylbiphenyl-4-yl) ether was obtained. The yield was 46%. The measurement results of the mass spectrum are described. H-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-C 3 H 7 MS m / e 330 (M +)

【００７５】[0075]

【化４】 Embedded image

【００７６】実施例２と同様にして、以下の化合物を得
ることができる。 H-Ph-CH(CH3)-CH2O-Ph-Ph-H CH3-Ph-CH(CH3)-CH2O-Ph-Ph-CH3 C2H5-Ph-CH(CH3)-CH2O-Ph-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-C≡CCH3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-CF3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-F CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-Cl CH3O-Ph-CH(CH3)-CH2O-Ph-Ph-C≡Ｎ ＣＨ３Ｏ−Ｐｈ−ＣＨ（ＣＨ３）−ＣＨ２Ｏ−Ｐｈ−Ｐ
ｈ（Ｆ）−Ｆ ＣＨ３Ｏ−Ｐｈ−ＣＨ（ＣＨ３）−ＣＨ２Ｏ−Ｐｈ−Ｐ
ｈ（ＦＦ）−ＦThe following compounds can be obtained in the same manner as in Example 2. H-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3) -CH 2 O-Ph- Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3) -CH 2 O-Ph-Ph-C 3 H 7 (CH 3) 2 CHCH 2 -Ph- CH (CH 3 ) -CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH ( CH 3 ) -CH 2 O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH ( CH 3 ) -CH 2 O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-C≡CCH 3 CH 3 O-Ph- CH (CH 3 ) -CH 2 O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph -Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-Ph-C≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 O-Ph-P
h (F) -F CH 3 O -Ph-CH (CH 3) -CH 2 O-Ph-P
h (FF) -F

【００７７】［実施例３］実施例１の第１ステップにお
いて、(S)-(+)-2-フェニルプロピオン酸のかわりに、
(S)-2-(4- メトキシフェニル)-3,3,3-トリフルオロプロ
ピオン酸625mg(2.67mmol) を用いる以外は実施例１と同
様に反応を行い、(S)-2-(4- メトキシフェニル)-3,3,3-
トリフルオロ-1- プロピル-4- ヘキシルオキシフェニル
エーテルを214mg(0.60mmol) 得た。マススペクトルの測
定結果を示す。 CH3O-Ph-CH(CF3)-CH2O-Ph-OC6H13 ＭＳ m/e 396(M+)Example 3 In the first step of Example 1, instead of (S)-(+)-2-phenylpropionic acid,
The reaction was carried out in the same manner as in Example 1 except that 625 mg (2.67 mmol) of (S) -2- (4-methoxyphenyl) -3,3,3-trifluoropropionic acid was used, and (S) -2- (4 -Methoxyphenyl) -3,3,3-
214 mg (0.60 mmol) of trifluoro-1-propyl-4-hexyloxyphenyl ether were obtained. The measurement result of a mass spectrum is shown. CH 3 O-Ph-CH ( CF 3) -CH 2 O-Ph-OC 6 H 13 MS m / e 396 (M +)

【００７８】[0078]

【化５】 Embedded image

【００７９】実施例３と同様にして、以下の化合物を得
ることができる。 H-Ph-CH(CF3)-CH2O-Ph-H CH3-Ph-CH(CF3)-CH2O-Ph-CH3 C2H5-Ph-CH(CF3)-CH2O-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2O-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2O-Ph-C ≡CCH3 CH3O-Ph-CH(CF3)-CH2O-Ph-CF3 CH3O-Ph-CH(CF3)-CH2O-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2O-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2O-Ph-F CH3O-Ph-CH(CF3)-CH2O-Ph-Cl CH3O-Ph-CH(CF3)-CH2O-Ph-C ≡N CH3O-Ph-CH(CF3)-CH2O-Ph(F)-F CH3O-Ph-CH(CF3)-CH2O-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 3. H-Ph-CH (CF 3 ) -CH 2 O-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 O-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -CH 2 O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3) -CH 2 O-Ph-C 3 H 7 (CH 3) 2 CHCH 2 -Ph-CH (CF 3) -CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-C ≡ CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-OCF 3 CH 3 O-Ph-CH ( CF 3 ) -CH 2 O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph -Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-C ≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph (F) -F CH 3 O-Ph -CH (CF 3 ) -CH 2 O-Ph (FF) -F

【００８０】［実施例４］実施例１の第１ステップにお
いて、(S)-(+)-2-フェニルプロピオン酸のかわりに、
(S)-2-(4- メトキシフェニル)-3,3,3-トリフルオロプロ
ピオン酸625mg(2.67mmol) を用い、第３ステップにおい
て、4-ヘキシルオキシフェノールのかわりに、4-（4-プ
ロピルフェニル）フェノールを 301mg(1.42mmol)用いる
以外は実施例１と同様に反応を行い、(S)-2-(4- メトキ
シフェニル)-3,3,3-トリフルオロ-1-プロピル-(4'- プ
ロピルビフェニル-4- イル）エーテルを253mg(0.61mmo
l) 得た。収率は44% であった。マススペクトルの測定
結果を示す。 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-C3H7 ＭＳ m/e 414(M+)Example 4 In the first step of Example 1, instead of (S)-(+)-2-phenylpropionic acid,
In the third step, 625 mg (2.67 mmol) of (S) -2- (4-methoxyphenyl) -3,3,3-trifluoropropionic acid was used instead of 4-hexyloxyphenol in the third step. The reaction was carried out in the same manner as in Example 1 except that 301 mg (1.42 mmol) of propylphenyl) phenol was used, and (S) -2- (4-methoxyphenyl) -3,3,3-trifluoro-1-propyl- ( 253mg (0.61mmo of 4'-propylbiphenyl-4-yl) ether
l) Got it. The yield was 44%. The measurement result of a mass spectrum is shown. CH 3 O-Ph-CH ( CF 3) -CH 2 O-Ph-Ph-C 3 H 7 MS m / e 414 (M +)

【００８１】[0081]

【化６】 Embedded image

【００８２】実施例４と同様にして、以下の化合物を得
ることができる。 H-Ph-CH(CF3)-CH2O-Ph-Ph-H CH3-Ph-CH(CF3)-CH2O-Ph-Ph-CH3 C2H5-Ph-CH(CF3)-CH2O-Ph-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-OC6H13 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-C≡CCH3 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-CF3 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-F CH3O-Ph-CH(CF3)-CH2O-Ph-Cl CH3O-Ph-CH(CF3)-CH2O-Ph-Ph-C≡N CH3O-Ph-CH(CF3)-CH2O-Ph-Ph(F)-F CH3O-Ph-CH(CF3)-CH2O-Ph-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 4. H-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph- CH (CF 3 ) -CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH ( CF 3 ) -CH 2 O-Ph-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O- Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-C≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-CF 3 CH 3 O-Ph-CH ( CF 3 ) -CH 2 O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 )- CH 2 O-Ph-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph-C≡ N CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 O-Ph-Ph (FF) -F

【００８３】［実施例５］実施例１の第１ステップにお
いて、(S)-(+)-2-フェニルプロピオン酸のかわりに、
(S)-3-フェニル酪酸438mg(2.67mmol) を用いる以外は実
施例１と同様に反応を行い、(S)-3-フェニル-1- ブチル
-4- ヘキシルオキシフェニルエーテルを214mg(0.50mmo
l) 得た。マススペクトルの測定結果を示す。 H-Ph-CH(CH3)-CH2CH2O-Ph-OC6H13 ＭＳ m/e 326(M+)Example 5 In the first step of Example 1, instead of (S)-(+)-2-phenylpropionic acid,
The reaction was carried out in the same manner as in Example 1 except that 438 mg (2.67 mmol) of (S) -3-phenylbutyric acid was used, and (S) -3-phenyl-1-butyl was used.
-4- Hexyloxyphenyl ether 214mg (0.50mmo
l) Got it. The measurement result of a mass spectrum is shown. H-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-OC 6 H 13 MS m / e 326 (M +)

【００８４】[0084]

【化７】 Embedded image

【００８５】実施例５と同様にして、以下の化合物を得
ることができる。 H-Ph-CH(CH3)-CH2CH2O-Ph-H CH3-Ph-CH(CH3)-CH2CH2O-Ph-CH3 C2H5-Ph-CH(CH3)-CH2CH2O-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2CH2O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2CH2O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-C≡CCH3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-CF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-F CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Cl CH3O-Ph-CH(CH3)-CH2CH2O-Ph-C≡N CH3O-Ph-CH(CH3)-CH2CH2O-Ph(F)-F CH3O-Ph-CH(CH3)-CH2CH2O-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 5. H-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph- CH (CH 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH ( CH 3 ) -CH 2 CH 2 O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH ( CH 3 ) -CH 2 CH 2 O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C≡CCH 3 CH 3 O-Ph- CH (CH 3 ) -CH 2 CH 2 O-Ph-CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 CH 2 O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O -Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-C≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph (F)- F CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph (FF) -F

【００８６】［実施例６］実施例１の第１ステップにお
いて、(S)-(+)-2-フェニルプロピオン酸のかわりに、
(S)-3-フェニル酪酸438mg(2.67mmol) を用い、第３ステ
ップにおいて、4-ヘキシルオキシフェノールのかわり
に、4-（4-プロピルフェニル）フェノールを 301mg(1.4
2mmol)用いる以外は実施例１と同様に反応を行い、(S)-
3-フェニル-1-ブチル-(4'- プロピルビフェニル-4- イ
ル）エーテルを214mg(0.51mmol) 得た。収率は36% であ
った。マススペクトルの測定結果を示す。 H-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C3H7 ＭＳ m/e 344(M+)Example 6 In the first step of Example 1, instead of (S)-(+)-2-phenylpropionic acid,
In the third step, using 438 mg (2.67 mmol) of (S) -3-phenylbutyric acid, 301 mg (1.4%) of 4- (4-propylphenyl) phenol was used instead of 4-hexyloxyphenol.
The reaction was carried out in the same manner as in Example 1 except that 2 mmol) was used, and (S)-
214 mg (0.51 mmol) of 3-phenyl-1-butyl- (4′-propylbiphenyl-4-yl) ether was obtained. The yield was 36%. The measurement result of a mass spectrum is shown. H-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 MS m / e 344 (M +)

【００８７】[0087]

【化８】 Embedded image

【００８８】実施例６と同様にして、以下の化合物を得
ることができる。 H-Ph-CH(CH3)-CH2CH2O-Ph-Ph-H CH3-Ph-CH(CH3)-CH2CH2O-Ph-Ph-CH3 C2H5-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C ≡CCH3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-CF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-F CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-Cl CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph-C ≡N CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph(F)-F CH3O-Ph-CH(CH3)-CH2CH2O-Ph-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 6. H-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-CH 3 C 2 H 5 -Ph -CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph- C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph- Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 )- CH 2 CH 2 O-Ph-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 CH 2 O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 CH 2 O-Ph-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph-C ≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -CH 2 CH 2 O-Ph-Ph (FF) -F

【００８９】［実施例７］実施例１の第１ステップにお
いて、(S)-(+)-2-フェニルプロピオン酸のかわりに、
(S)-3-(4- メトキシフェニル)-4,4,4-トリフルオロ酪酸
625mg(2.67mmol) を用いる以外は実施例１と同様に反応
を行い、(S)-3-(4- メトキシフェニル)-4,4,4-トリフル
オロ-1- ブチル-4- ヘキシルオキシフェニルエーテルを
214mg(0.69mmol) 得た。マススペクトルの測定結果を示
す。 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-OC6H13 ＭＳ ｍ／ｅ ４１０（Ｍ＋）Example 7 In the first step of Example 1, instead of (S)-(+)-2-phenylpropionic acid,
(S) -3- (4-methoxyphenyl) -4,4,4-trifluorobutyric acid
The reaction was carried out in the same manner as in Example 1 except that 625 mg (2.67 mmol) was used, and (S) -3- (4-methoxyphenyl) -4,4,4-trifluoro-1-butyl-4-hexyloxyphenyl Ether
214 mg (0.69 mmol) were obtained. The measurement results of mass spectrum are shown. CH 3 O-Ph-CH ( CF 3) -CH 2 CH 2 O-Ph-OC 6 H 13 MS m / e 410 (M +)

【００９０】[0090]

【化９】 Embedded image

【００９１】実施例７と同様にして、以下の化合物を得
ることができる。 H-Ph-CH(CF3)-CH2CH2O-Ph-H CH3-Ph-CH(CF3)-CH2CH2O-Ph-CH3 C2H5-Ph-CH(CF3)-CH2CH2O-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2CH2O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2CH2O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-C≡CCH3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-CF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-F CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Cl CH3O-Ph-CH(CF3)-CH2CH2O-Ph-C≡N CH3O-Ph-CH(CF3)-CH2CH2O-Ph(F)-F CH3O-Ph-CH(CF3)-CH2CH2O-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 7. H-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph- CH (CF 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-C 3 H 7 CH 3 O-Ph-CH ( CF 3 ) -CH 2 CH 2 O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O- Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-C≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-CF 3 CH 3 O-Ph-CH ( CF 3 ) -CH 2 CH 2 O-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 )- CH 2 CH 2 O-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph- C≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph (FF)- F

【００９２】［実施例８］実施例１の第１ステップにお
いて、(S)-(+)-2-フェニルプロピオン酸のかわりに、
(S)-3-(4- メトキシフェニル)-4,4,4-トリフルオロ酪酸
625mg(2.67mmol) を用い、第３ステップにおいて、4-ヘ
キシルオキシフェノールのかわりに、4-（４−プロピル
フェニル）フェノールを ３０１ｍｇ（１．４２ｍｍｏ
ｌ）用いる以外は実施例１と同様に反応を行い、(S)-3-
(4- メトキシフェニル)-4,4,4-トリフルオロ-1- ブチル
-(4'- プロピルビフェニル-4- イル) エーテルを253mg
(0.59mmol) 得た。マススペクトルの測定結果を示す。 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C3H7 ＭＳ m/e 428(M+)Example 8 In the first step of Example 1, instead of (S)-(+)-2-phenylpropionic acid,
(S) -3- (4-methoxyphenyl) -4,4,4-trifluorobutyric acid
Using 625 mg (2.67 mmol), in the third step, 301 mg (1.42 mmol) of 4- (4-propylphenyl) phenol was used instead of 4-hexyloxyphenol.
l) The reaction was carried out in the same manner as in Example 1 except that (S) -3-
(4-methoxyphenyl) -4,4,4-trifluoro-1-butyl
253 mg of-(4'-propylbiphenyl-4-yl) ether
(0.59 mmol) was obtained. The measurement result of a mass spectrum is shown. CH 3 O-Ph-CH ( CF 3) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 MS m / e 428 (M +)

【００９３】[0093]

【化１０】 Embedded image

【００９４】実施例８と同様にして、以下の化合物を得
ることができる。 H-Ph-CH(CF3)-CH2CH2O-Ph-H CH3-Ph-CH(CF3)-CH2CH2O-Ph-Ph-CH3 C2H5-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C ≡CCH3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-CF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-F CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-Cl CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph-C ≡N CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph(F)-F CH3O-Ph-CH(CF3)-CH2CH2O-Ph-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 8. H-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph- Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O -Ph-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph-C ≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph -Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 CH 2 O-Ph-Ph (FF) -F

【００９５】［実施例９］(S)-(+)-2-フェニルプロピオ
ン酸 600mg(4mmol) 、塩化チオニルを714mg(6mmol)およ
びテトラクロロエチレンを5ml 仕込み、N,N-ジメチルア
ニリンを数滴添加後、２５℃にて８時間撹拌した。溶媒
および過剰の塩化チオニルを減圧留去後、4-ヘキシルオ
キシフェノール776mg(4mmol)をトルエン2ml で溶解した
溶液を滴下し、さらにピリジン288mg(4mmol)およびトル
エン3ml を加え、２５℃にて２時間撹拌した。次いで、
水10mlを加え、分液後、水層を酢酸エチルで抽出し、油
層とあわせて水洗、乾燥後、溶媒を留去し、得られた粗
体を薄層クロマトグラフィ（展開溶媒はヘキサン５に対
し酢酸エチル１の混合溶媒を用いた）で精製し、(S)-2-
フェニルプロピオン酸(4- ヘキシルオキシフェニル) エ
ステルを782mg(2.4mmol)得た。収率は60% であった。マ
ススペクトルの測定結果を示す。 H-Ph-CH(CH3)-C(O)O-Ph-OC6H13 ＭＳ m/e 326(M+)Example 9 600 mg (4 mmol) of (S)-(+)-2-phenylpropionic acid, 714 mg (6 mmol) of thionyl chloride and 5 ml of tetrachloroethylene were charged, and several drops of N, N-dimethylaniline were added. And stirred at 25 ° C. for 8 hours. After evaporating the solvent and excess thionyl chloride under reduced pressure, a solution of 776 mg (4 mmol) of 4-hexyloxyphenol dissolved in 2 ml of toluene was added dropwise. Stirred. Then
10 ml of water was added, and after separation, the aqueous layer was extracted with ethyl acetate, washed with water and dried together with the oil layer, and the solvent was distilled off. The obtained crude product was subjected to thin-layer chromatography (developing solvent was hexane 5 Using a mixed solvent of ethyl acetate 1) to give (S) -2-
782 mg (2.4 mmol) of phenylpropionic acid (4-hexyloxyphenyl) ester was obtained. The yield was 60%. The measurement result of a mass spectrum is shown. H-Ph-CH (CH 3 ) -C (O) O-Ph-OC 6 H 13 MS m / e 326 (M +)

【００９６】[0096]

【化１１】 Embedded image

【００９７】実施例９と同様にして、以下の化合物を得
ることができる。 H-Ph-CH(CH3)-C(O)O-Ph-H CH3-Ph-CH(CH3)-C(O)O-Ph-CH3 C2H5-Ph-CH(CH3)-C(O)O-Ph-C2H5 C3H7-Ph-CH(CH3)-C(O)O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-C(O)O-Ph-C3H7 CH3O-Ph-CH(CH3)-C(O)O-Ph-C3H7 CH3O-Ph-CH(CH3)-C(O)O-Ph-OC6H13 CH3O-Ph-CH(CH3)-C(O)O-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-C(O)O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-C(O)O-Ph-C≡CCH3 CH3O-Ph-CH(CH3)-C(O)O-Ph-CF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-OCF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-F CH3O-Ph-CH(CH3)-C(O)O-Ph-Cl CH3O-Ph-CH(CH3)-C(O)O-Ph-C≡N CH3O-Ph-CH(CH3)-C(O)O-Ph(F)-F CH3O-Ph-CH(CH3)-C(O)O-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 9. H-Ph-CH (CH 3 ) -C (O) O-Ph-H CH 3 -Ph-CH (CH 3 ) -C (O) O-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3 ) -C (O) O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -C (O) O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph- CH (CH 3 ) -C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH ( CH 3 ) -C (O) O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH ( CH 3 ) -C (O) O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-C≡CCH 3 CH 3 O-Ph- CH (CH 3 ) -C (O) O-Ph-CF 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 )- C (O) O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-F CH 3 O-Ph-CH (CH 3 ) -C (O) O -Ph-Cl CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-C≡N CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph (F)- F CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph (FF) -F

【００９８】［実施例１０］実施例９において、4-ヘキ
シルオキシフェノールのかわりに、4-（4-プロピルフェ
ニル）フェノールを848mg(4mmol)用いる以外は実施例９
と同様に反応を行い、(S)-2-フェニルプロピオン酸(4'-
プロピルビフェニル-4- イル) エステルを860mg(2.5mmo
l)得た。収率は63% であった。マススペクトルの測定結
果を示す。 H-Ph-CH(CH3)-C(O)O-Ph-Ph-C3H7 ＭＳ m/e 344(M+)Example 10 Example 9 was repeated except that 848 mg (4 mmol) of 4- (4-propylphenyl) phenol was used instead of 4-hexyloxyphenol.
(S) -2-phenylpropionic acid (4'-
860 mg (2.5 mmo) of propylbiphenyl-4-yl) ester
l) Got it. The yield was 63%. The measurement result of a mass spectrum is shown. H-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-C 3 H 7 MS m / e 344 (M +)

【００９９】[0099]

【化１２】 Embedded image

【０１００】実施例１０と同様にして、以下の化合物を
得ることができる。 H-Ph-CH(CH3)-C(O)O-Ph-Ph-H CH3-Ph-CH(CH3)-C(O)O-Ph-Ph-CH3 C2H5-Ph-CH(CH3)-C(O)O-Ph-Ph-C2H5 C3H7-Ph-CH(CH3)-C(O)O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-OC6H13 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-C ≡CCH3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-CF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-OCF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-F CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-Cl CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph-C ≡N CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph(F)-F CH3O-Ph-CH(CH3)-C(O)O-Ph-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 10. H-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-H CH 3 -Ph-CH (CH 3 ) -C (O) O-Ph-Ph-CH 3 C 2 H 5 -Ph -CH (CH 3 ) -C (O) O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -C (O) O-Ph-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CH 3 ) -C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph- C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph- Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 )- C (O) O-Ph-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CH 3 )- C (O) O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 )- C (O) O-Ph-Ph-F CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph-C ≡N CH 3 O-Ph-CH (CH 3 ) -C (O) O-Ph-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -C (O ) O-Ph-Ph (FF) -F

【０１０１】［実施例１１］実施例９において、(S)-
(+)-2-フェニルプロピオン酸のかわりに、(S)-2-(4-メ
トキシフェニル)-3,3,3-トリフルオロプロピオン酸936m
g(4mmol)用いる以外は実施例９と同様に反応を行い、
(S)-2-(4- メトキシフェニル)-3,3,3-トリフルオロプロ
ピオン酸(4- ヘキシルオキシフェニル) エステルを782m
g(2.8mmol)得た。収率は70% であった。マススペクトル
の測定結果を示す。 CH3O-Ph-CH(CF3)-C(O)O-Ph-OC6H13 ＭＳ ｍ／ｅ ４１０（Ｍ＋）[Embodiment 11] In Embodiment 9, the (S)-
Instead of (+)-2-phenylpropionic acid, (S) -2- (4-methoxyphenyl) -3,3,3-trifluoropropionic acid 936m
The reaction was carried out in the same manner as in Example 9 except that g (4 mmol) was used,
782m of (S) -2- (4-methoxyphenyl) -3,3,3-trifluoropropionic acid (4-hexyloxyphenyl) ester
g (2.8 mmol) were obtained. The yield was 70%. The measurement result of a mass spectrum is shown. CH 3 O-Ph-CH ( CF 3) -C (O) O-Ph-OC 6 H 13 MS m / e 410 (M +)

【０１０２】[0102]

【化１３】 Embedded image

【０１０３】実施例１１と同様にして、以下の化合物を
得ることができる。 H-Ph-CH(CF3)-C(O)O-Ph-H CH3-Ph-CH(CF3)-C(O)O-Ph-CH3 C2H5-Ph-CH(CF3)-C(O)O-Ph-C2H5 C3H7-Ph-CH(CF3)-C(O)O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-C(O)O-Ph-C3H7 CH3O-Ph-CH(CF3)-C(O)O-Ph-C3H7 CH3O-Ph-CH(CF3)-C(O)O-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-C(O)O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-C(O)O-Ph-C≡CCH3 CH3O-Ph-CH(CF3)-C(O)O-Ph-CF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-OCF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-F CH3O-Ph-CH(CF3)-C(O)O-Ph-Cl CH3O-Ph-CH(CF3)-C(O)O-Ph-C≡N CH3O-Ph-CH(CF3)-C(O)O-Ph(F)-F CH3O-Ph-CH(CF3)-C(O)O-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 11. H-Ph-CH (CF 3 ) -C (O) O-Ph-H CH 3 -Ph-CH (CF 3 ) -C (O) O-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -C (O) O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -C (O) O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph- CH (CF 3 ) -C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH ( CF 3 ) -C (O) O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O- Ph-CH (CF 3 ) -C (O) O-Ph-C≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-CF 3 CH 3 O-Ph-CH ( CF 3 ) -C (O) O-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 )- C (O) O-Ph-F CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph- C≡N CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph (FF)- F

【０１０４】［実施例１２］実施例９において、(S)-
(+)-2-フェニルプロピオン酸のかわりに、(S)-2-(4-メ
トキシフェニル)-3,3,3-トリフルオロプロピオン酸936m
g(4mmol)用い、4-ヘキシルオキシフェノールのかわり
に、4-（4-プロピルフェニル）フェノールを848mg(4mmo
l)用いる以外は実施例９と同様に反応を行い、(S)-2-(4
- メトキシフェニル)-3,3,3-トリフルオロプロピオン酸
(4'-プロピルビフェニル-4- イル) エステルを782mg(2.
5mmol)得た。収率は63% であった。マススペクトルの測
定結果を示す。 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-C3H7 ＭＳ m/e 428(M+)[Embodiment 12] In Embodiment 9, (S)-
Instead of (+)-2-phenylpropionic acid, (S) -2- (4-methoxyphenyl) -3,3,3-trifluoropropionic acid 936m
g (4 mmol) and 848 mg (4 mmo) of 4- (4-propylphenyl) phenol instead of 4-hexyloxyphenol.
l) The reaction was carried out in the same manner as in Example 9 except that l) was used, and (S) -2- (4
-Methoxyphenyl) -3,3,3-trifluoropropionic acid
784 mg of (4'-propylbiphenyl-4-yl) ester (2.
5 mmol). The yield was 63%. The measurement result of a mass spectrum is shown. CH 3 O-Ph-CH ( CF 3) -C (O) O-Ph-Ph-C 3 H 7 MS m / e 428 (M +)

【０１０５】[0105]

【化１４】 Embedded image

【０１０６】実施例１２と同様にして、以下の化合物を
得ることができる。 H-Ph-CH(CF3)-C(O)O-Ph-H CH3-Ph-CH(CF3)-C(O)O-Ph-Ph-CH3 C2H5-Ph-CH(CF3)-C(O)O-Ph-Ph-C2H5 C3H7-Ph-CH(CF3)-C(O)O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-OC6H13 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-C ≡CCH3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-CF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-OCF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-F CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-Cl CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph-C ≡N CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph(F)-F CH3O-Ph-CH(CF3)-C(O)O-Ph-Ph(FF)-FThe following compounds can be obtained in the same manner as in Example 12. H-Ph-CH (CF 3 ) -C (O) O-Ph-H CH 3 -Ph-CH (CF 3 ) -C (O) O-Ph-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -C (O) O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -C (O) O-Ph-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CF 3 ) -C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-OC 6 H 13 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph- Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -C ( O) O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-F CH 3 O-Ph-CH (CF 3 ) -C (O) O -Ph-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph-C ≡N CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph -Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -C (O) O-Ph-Ph (FF) -F

【０１０７】［実施例１３］実施例９において、(S)-
(+)-2-フェニルプロピオン酸のかわりに、(S)-3-フェニ
ル酪酸656mg(4mmol)を用いる以外は実施例９と同様に反
応を行い、(S)-3-フェニル酪酸(4- ヘキシルオキシフェ
ニル) エステルを782mg(2.4mmol)得た。収率は60% であ
った。マススペクトルの測定結果を示す。 H-Ph-CH(CH3)-CH2C(O)O-Ph-OC6H13 ＭＳ m/e 340(M+)[Thirteenth Embodiment] In the ninth embodiment, the (S)-
The reaction was carried out in the same manner as in Example 9 except that 656 mg (4 mmol) of (S) -3-phenylbutyric acid was used instead of (+)-2-phenylpropionic acid. Hexyloxyphenyl) ester was obtained in an amount of 782 mg (2.4 mmol). The yield was 60%. The measurement result of a mass spectrum is shown. H-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-OC 6 H 13 MS m / e 340 (M +)

【０１０８】[0108]

【化１５】 Embedded image

【０１０９】実施例１３と同様にして、以下の化合物を
得ることができる。 H-Ph-CH(CH3)-CH2C(O)O-Ph-H CH3-Ph-CH(CH3)-CH2C(O)O-Ph-CH3 C2H5-Ph-CH(CH3)-CH2C(O)O-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2C(O)O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2C(O)O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-C ≡CCH3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-CF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-F CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Cl CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-C ≡N CH3O-Ph-CH(CH3)-CH2C(O)O-Ph(F)-F CH3O-Ph-CH(CH3)-CH2C(O)O-Ph(FF)-FIn the same manner as in Example 13, the following compounds can be obtained. H-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-H CH 3 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-CH 3 C 2 H 5 -Ph -CH (CH 3 ) -CH 2 C (O) O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph- C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-OC 6 H 13 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O- Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 )- CH 2 C (O) O-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-CF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 C (O) O-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 )- CH 2 C (O) O-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 C ( O) O-Ph-C ≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph (FF) -F

【０１１０】［実施例１４］実施例９において、(S)-
(+)-2-フェニルプロピオン酸のかわりに、(S)-3-フェニ
ル酪酸656mg(4mmol)を用い、4-ヘキシルオキシフェノー
ルのかわりに、4-（4-プロピルフェニル）フェノールを
848mg(4mmol) 用いる以外は実施例９と同様に反応を行
い、(S)-3-フェニル酪酸(4'-プロピルビフェニル-4- イ
ル) エステルを788mg(2.2mmol)得た。収率は55% であっ
た。マススペクトルの測定結果を示す。 H-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C3H7 ＭＳ m/e 358(M+)[Embodiment 14] In the ninth embodiment, (S)-
Instead of (+)-2-phenylpropionic acid, use 656 mg (4 mmol) of (S) -3-phenylbutyric acid, and replace 4- (4-propylphenyl) phenol with 4-hexyloxyphenol.
The reaction was carried out in the same manner as in Example 9 except that 848 mg (4 mmol) was used, to obtain 788 mg (2.2 mmol) of (S) -3-phenylbutyric acid (4′-propylbiphenyl-4-yl) ester. The yield was 55%. The measurement results of mass spectrum are shown. H-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-C 3 H 7 MS m / e 358 (M +)

【０１１１】[0111]

【化１６】 Embedded image

【０１１２】実施例１４と同様にして、以下の化合物を
得ることができる。 H-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-H CH3-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-CH3 C2H5-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C2H5 C3H7-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-OC6H13 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C≡CCH3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-CF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-OCF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-F CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-Cl CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph-C≡N CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph(F)-F CH3O-Ph-CH(CH3)-CH2C(O)O-Ph-Ph(FF)-FIn the same manner as in Example 14, the following compounds can be obtained. H-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-H CH 3 -Ph-CH (CH 3) -CH 2 C (O) O-Ph-Ph-CH 3 C 2 H 5 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph- Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 )- CH 2 C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-OC 6 H 13 CH 3 O-Ph- CH (CH 3) -CH 2 C (O) O-Ph-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CH 3) -CH 2 C (O) O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-C≡CCH 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C ( O) O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-F CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-Cl CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph-C≡N CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph (F) -F CH 3 O-Ph-CH (CH 3 ) -CH 2 C (O) O-Ph-Ph (FF) -F

【０１１３】［実施例１５］実施例９において、(S)-
(+)-2-フェニルプロピオン酸のかわりに、(S)-3-(4-メ
トキシフェニル)-4,4,4-トリフルオロ酪酸992mg(4mmol)
用いる以外は実施例９と同様に反応を行い、(S)-3-(4-
メトキシフェニル)-4,4,4-トリフルオロ酪酸(4- ヘキシ
ルオキシフェニル) エステルを890mg(2.1mmol)得た。収
率は53% であった。マススペクトルの測定結果を示す。 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-OC6H13 ＭＳ m/e 424(M+)[Embodiment 15] In Embodiment 9, the (S)-
Instead of (+)-2-phenylpropionic acid, (S) -3- (4-methoxyphenyl) -4,4,4-trifluorobutyric acid 992 mg (4 mmol)
The reaction was carried out in the same manner as in Example 9 except for using (S) -3- (4-
890 mg (2.1 mmol) of methoxyphenyl) -4,4,4-trifluorobutyric acid (4-hexyloxyphenyl) ester was obtained. The yield was 53%. The measurement result of a mass spectrum is shown. CH 3 O-Ph-CH ( CF 3) -CH 2 C (O) O-Ph-OC 6 H 13 MS m / e 424 (M +)

【０１１４】[0114]

【化１７】 Embedded image

【０１１５】実施例１５と同様にして、以下の化合物を
得ることができる。 H-Ph-CH(CF3)-CH2C(O)O-Ph-H CH3-Ph-CH(CF3)-CH2C(O)O-Ph-CH3 C2H5-Ph-CH(CF3)-CH2C(O)O-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2C(O)O-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2C(O)O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-C ≡CCH3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-CF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-F CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Cl CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-C ≡N CH3O-Ph-CH(CF3)-CH2C(O)O-Ph(F)-F CH3O-Ph-CH(CF3)-CH2C(O)O-Ph(FF)-FIn the same manner as in Example 15, the following compounds can be obtained. H-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-CH 3 C 2 H 5 -Ph -CH (CF 3 ) -CH 2 C (O) O-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph- C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-CH 2 OC 2 H 5 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-C ≡CCH 3 CH 3 O-Ph-CH (CF 3 )- CH 2 C (O) O-Ph-CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-C ≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O ) O-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph (FF) -F

【０１１６】［実施例１６］実施例９において、(S)-
(+)-2-フェニルプロピオン酸のかわりに、(S)-3-(4-メ
トキシフェニル)-4,4,4-トリフルオロ酪酸992mg(4mmol)
用い、4-ヘキシルオキシフェノールのかわりに、4-（4-
プロピルフェニル）フェノールを848mg(4mmol)用いる以
外は実施例９と同様に反応を行い、(S)-3-(4- メトキシ
フェニル)-4,4,4-トリフルオロ酪酸(4'-プロピルビフェ
ニル-4- イル) エステルを890mg(2.6mmol)得た。収率は
65% であった。マススペクトルの測定結果を示す。 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C3H7 ＭＳ ｍ／ｅ ４４２（Ｍ＋）[Embodiment 16] In Embodiment 9, the (S)-
Instead of (+)-2-phenylpropionic acid, (S) -3- (4-methoxyphenyl) -4,4,4-trifluorobutyric acid 992 mg (4 mmol)
Used, instead of 4-hexyloxyphenol, 4- (4-
(S) -3- (4-methoxyphenyl) -4,4,4-trifluorobutyric acid (4′-propylbiphenyl) was reacted in the same manner as in Example 9 except that 848 mg (4 mmol) of propylphenyl) phenol was used. -4-yl) 890 mg (2.6 mmol) of the ester were obtained. The yield is
65%. The measurement result of a mass spectrum is shown. CH 3 O-Ph-CH ( CF 3) -CH 2 C (O) O-Ph-Ph-C 3 H 7 MS m / e 442 (M +)

【０１１７】[0117]

【化１８】 Embedded image

【０１１８】実施例１６と同様にして、以下の化合物を
得ることができる。 H-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-H CH3-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-CH3 C2H5-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C2H5 C3H7-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C3H7 (CH3)2CHCH2-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C3H7 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-CH2OC2H5 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-CH2CH2CH=CHCH3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C≡CCH3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-CF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-OCF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-OCH2CF3 CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-F CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-Cl CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph-C≡N CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph(F)-F CH3O-Ph-CH(CF3)-CH2C(O)O-Ph-Ph(FF)-FIn the same manner as in Example 16, the following compounds can be obtained. H-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-H CH 3 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-CH 3 C 2 H 5 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-C 2 H 5 C 3 H 7 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph- Ph-C 3 H 7 (CH 3 ) 2 CHCH 2 -Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 )- CH 2 C (O) O-Ph-Ph-C 3 H 7 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-CH 2 OC 2 H 5 CH 3 O- Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-CH 2 CH 2 CH = CHCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph- Ph-C≡CCH 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-OCF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-OCH 2 CF 3 CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-F CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-Cl CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph-C≡N CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph (F) -F CH 3 O-Ph-CH (CF 3 ) -CH 2 C (O) O-Ph-Ph (FF) -F

【０１１９】［液晶組成物の調製例］メルク社製液晶組
成物（商品名：ＺＬＩ−１５６５）の９５重量％に、実
施例１で合成した式２３の化合物［(S)-(+)-2-フェニル
-1- プロピル-4- ヘキシルオキシフェニルエーテル］を
５重量％加えて液晶組成物（イ）を得た。また、ＺＬＩ
−１５６５の９９重量％に、式２３の化合物を１重量％
加えて液晶組成物（ニ）を得た。[Preparation Example of Liquid Crystal Composition] In 95% by weight of a liquid crystal composition (trade name: ZLI-1565) manufactured by Merck, the compound of formula 23 synthesized in Example 1 [(S)-(+)- 2-phenyl
-1-propyl-4-hexyloxyphenyl ether] was added in an amount of 5% by weight to obtain a liquid crystal composition (a). Also, ZLI
1 wt% of the compound of formula 23 to 99 wt% of -1565
In addition, a liquid crystal composition (d) was obtained.

【０１２０】［液晶組成物の比較調製例］ＺＬＩ−１５
６５の９５重量％にコレステリルノナノエートＣＮ（コ
レステリック骨格を有する化合物からなる市販のカイラ
ル剤）を５重量％加えた液晶組成物（ロ）、ＺＬＩ−１
５６５の９５重量％にＳ−８１１（市販のカイラル剤）
を５重量％加えた液晶組成物（ハ）を得た。Ｓ−８１１
の構造は、下記のとおりである。 CH3O-Ph-COO-Ph-COOCH(CH3)C6H13 [Comparative Preparation Example of Liquid Crystal Composition] ZLI-15
A liquid crystal composition (b) in which 5% by weight of cholesteryl nonanoate CN (a commercially available chiral agent comprising a compound having a cholesteric skeleton) is added to 95% by weight of 65, ZLI-1
S-811 (commercially available chiral agent) in 95% by weight of 565
Was added to obtain a liquid crystal composition (c). S-811
Is as follows. CH 3 O-Ph-COO-Ph-COOCH (CH 3 ) C 6 H 13

【０１２１】また、ＺＬＩ−１５６５の９９重量％にコ
レステリルノナノエートＣＮを１重量％加えた液晶組成
物（ホ）、ＺＬＩ−１５６５の９９重量％にＳ−８１１
を１重量％加えた液晶組成物（へ）を得た。Further, a liquid crystal composition (e) in which 1% by weight of cholesteryl nonanoate CN was added to 99% by weight of ZLI-1565, and S-811 was added to 99% by weight of ZLI-1565.
Was added to obtain a liquid crystal composition (H).

【０１２２】［動粘度の評価］液晶組成物（イ）、
（ロ）および（ハ）の動粘度を測定し、それぞれの動粘
度から式２３の化合物、コレステリルノナノエートＣＮ
（ＣＮと記す）、Ｓ−８１１の２５℃または０℃での動
粘度ν（単位：ｃＳｔ）を１００％外挿値として算出し
た。結果を表１に示す。[Evaluation of Kinematic Viscosity] The liquid crystal composition (a)
The kinematic viscosities of (b) and (c) were measured, and the compound of formula 23, cholesteryl nonanoate CN
The kinematic viscosity ν (unit: cSt) at 25 ° C. or 0 ° C. of S-811 was calculated as an extrapolated value of 100%. Table 1 shows the results.

【０１２３】［ヘリカルねじれ能の評価］液晶組成物
（ニ）、（ホ）および（ヘ）を用い、添加した式２３の
化合物、ＣＮ、Ｓ−８１１の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。結果を表１に示す。[Evaluation of Helical Twisting Ability] Using the liquid crystal compositions (d), (e) and (f), a helical pitch length p (unit: 25 ° C.) of the compound of the formula 23, CN, and S-811 was added. μm) was measured by the Cano wedge method. Table 1 shows the results.

【０１２４】[0124]

【表１】 [Table 1]

【０１２５】[0125]

【発明の効果】本発明の新規な光学活性化合物（式１）
は、優れた液晶組成物を提供しうる有用な化合物であ
る。該化合物は、ヘリカルねじれ能（helical twising
power)が大きく、かつ、低温から高温にわたり粘性が小
さいことから、液晶組成物に少量を添加しただけで、満
足な性能が得られ、かつ、液晶組成物は低粘性となる利
点がある。さらに本発明の該液晶組成物を用いた液晶電
気光学素子は、高速応答性を示しうる。また、粘性の温
度依存性が小さく、低温であっても低粘性であることか
ら、外的環境の変化があっても性能を維持できる利点も
ある。The novel optically active compound of the present invention (formula 1)
Is a useful compound that can provide an excellent liquid crystal composition. The compound has a helical twising ability.
power) is large and the viscosity is low from low temperature to high temperature. Therefore, satisfactory performance can be obtained only by adding a small amount to the liquid crystal composition, and the liquid crystal composition has an advantage of low viscosity. Further, a liquid crystal electro-optical element using the liquid crystal composition of the present invention can exhibit high-speed response. In addition, since the viscosity has low temperature dependence and is low in viscosity even at low temperatures, there is an advantage that the performance can be maintained even when there is a change in the external environment.

【図面の簡単な説明】[Brief description of the drawings]

【図１】本発明の実施例１で合成した化合物（式２３）
のＧＣ−ＭａｓｓスペクトルFIG. 1 shows a compound synthesized in Example 1 of the present invention (Formula 23).
GC-Mass spectrum of

【図２】本発明の実施例１で合成した化合物（式２３）
の 1Ｈ−ＮＭＲスペクトルFIG. 2 A compound synthesized in Example 1 of the present invention (Formula 23)
1 H-NMR spectrum of

【図３】本発明の実施例１で合成した化合物（式２３）
の13Ｃ−ＮＭＲスペクトルFIG. 3 shows a compound synthesized in Example 1 of the present invention (Formula 23).
13 C-NMR spectrum of

【図４】本発明の実施例１で合成した化合物（式２３）
のＩＲスペクトルFIG. 4 is a compound (Formula 23) synthesized in Example 1 of the present invention.
IR spectrum of

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｇ０２Ｆ 1/13 ５００ Ｇ０２Ｆ 1/13 ５００ // Ｃ０７Ｍ 7:00 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code FI G02F 1/13 500 G02F 1/13 500 // C07M 7:00

Claims (6)

【特許請求の範囲】[Claims] 【請求項１】下式１で表される光学活性化合物。 R1-A1-CHX-Y-A2-(A3)m-R2 ・・・式１ ただし、式１中の記号は、以下の意味を示す。 Ａ1 ：非置換の１，４−フェニレン基。 Ａ2 、Ａ3 ：相互に独立して、非置換の１，４−フェニ
レン基、１個以上のハロゲン原子が置換した１，４−フ
ェニレン基、非置換のトランス−１, ４−シクロヘキシ
レン基、または１個以上のハロゲン原子が置換したトラ
ンス−１, ４−シクロヘキシレン基。 Ｒ1 、Ｒ2 ：炭素数１〜１０の１価脂肪族炭化水素基、
炭素数１〜１０のフッ素化１価脂肪族炭化水素基、水素
原子、ハロゲン原子、またはシアノ基であり、炭素数１
〜１０の１価脂肪族炭化水素基または炭素数１〜１０の
フッ素化１価脂肪族炭化水素基である場合には、該基中
の炭素−炭素結合間にエーテル性の酸素原子が挿入され
ていてもよく、該基と、Ａ1 またはＡ3 とを連結する炭
素−炭素結合間にエーテル性の酸素原子が挿入されてい
てもよく、該基中の−ＣＨ2 −部分がカルボニル基に置
換されていてもよい。 Ｘ：−ＣＨ3 または−ＣＦ3 。 Ｙ：−ＣＯＯ−、−ＣＨ2 ＣＯＯ−、−ＣＨ2 Ｏ−、ま
たは−ＣＨ2 ＣＨ2 Ｏ−。 ｍ：０または１。1. An optically active compound represented by the following formula 1. R 1 -A 1 -CHX-YA 2- (A 3 ) m -R 2 Formula 1 where the symbols in the formula 1 have the following meanings. A 1 : an unsubstituted 1,4-phenylene group. A 2 , A 3 : independently of each other, an unsubstituted 1,4-phenylene group, a 1,4-phenylene group substituted by one or more halogen atoms, an unsubstituted trans-1,4-cyclohexylene group Or a trans-1,4-cyclohexylene group substituted by one or more halogen atoms. R 1 and R 2 : a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms;
A fluorinated monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, a hydrogen atom, a halogen atom, or a cyano group;
In the case of a monovalent aliphatic hydrocarbon group of 10 to 10 or a fluorinated monovalent aliphatic hydrocarbon group of 1 to 10 carbon atoms, an etheric oxygen atom is inserted between carbon-carbon bonds in the group. And an etheric oxygen atom may be inserted between the carbon-carbon bond connecting the group to A 1 or A 3, and the -CH 2 -moiety in the group may be a carbonyl group. It may be substituted. X: -CH 3 or -CF 3. Y: -COO -, - CH 2 COO -, - CH 2 O-, or -CH 2 CH 2 O-. m: 0 or 1. 【請求項２】Ａ2 が非置換の１，４−フェニレン基また
は１個以上のハロゲン原子が置換した１，４−フェニレ
ン基であり、かつ、ｍが０である請求項１記載の光学活
性化合物。2. The optical activity according to claim 1, wherein A 2 is an unsubstituted 1,4-phenylene group or a 1,4-phenylene group substituted with one or more halogen atoms, and m is 0. Compound. 【請求項３】Ａ2 およびＡ3 が、それぞれ、非置換の
１，４−フェニレン基または１個以上のハロゲン原子が
置換した１，４−フェニレン基であり、かつｍが１であ
る請求項１記載の光学活性化合物。3. A 2 and A 3 are each an unsubstituted 1,4-phenylene group or a 1,4-phenylene group substituted with one or more halogen atoms, and m is 1. 2. The optically active compound according to 1. 【請求項４】請求項１、２または３記載の光学活性化合
物を含む液晶組成物。4. A liquid crystal composition comprising the optically active compound according to claim 1, 2 or 3. 【請求項５】液晶組成物中に請求項１、２または３記載
の光学活性化合物を０．１〜１０重量％含む液晶組成
物。5. A liquid crystal composition comprising 0.1 to 10% by weight of the optically active compound according to claim 1, 2 or 3 in the liquid crystal composition. 【請求項６】請求項４または５記載の液晶組成物を用い
た液晶電気表示素子。6. A liquid crystal electric display device using the liquid crystal composition according to claim 4.
JP5645097A 1997-03-11 1997-03-11 Optically active compound and liquid crystal composition containing the same Pending JPH10251185A (en)

Priority Applications (1)

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JPH10251185A true JPH10251185A (en) 1998-09-22

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Country Link
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7108895B2 (en) 2001-02-08 2006-09-19 Seimi Chemical Co., Ltd. Liquid crystal composition containing an optically active compound and liquid crystal electro-optical element
JP2010275463A (en) * 2009-05-29 2010-12-09 Dic Corp Cholesteric liquid crystal composition for active matrix driving

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7108895B2 (en) 2001-02-08 2006-09-19 Seimi Chemical Co., Ltd. Liquid crystal composition containing an optically active compound and liquid crystal electro-optical element
JP2010275463A (en) * 2009-05-29 2010-12-09 Dic Corp Cholesteric liquid crystal composition for active matrix driving

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