JPS63295534A - Optically active ester compound - Google Patents
Optically active ester compoundInfo
- Publication number
- JPS63295534A JPS63295534A JP62130293A JP13029387A JPS63295534A JP S63295534 A JPS63295534 A JP S63295534A JP 62130293 A JP62130293 A JP 62130293A JP 13029387 A JP13029387 A JP 13029387A JP S63295534 A JPS63295534 A JP S63295534A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- optically active
- benzoic acid
- confirmed
- 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.)
- Granted
Links
- -1 ester compound Chemical class 0.000 title claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 22
- 150000001875 compounds Chemical class 0.000 abstract description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 12
- 239000005711 Benzoic acid Substances 0.000 abstract description 10
- 235000010233 benzoic acid Nutrition 0.000 abstract description 10
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 9
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract description 3
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000003287 optical effect Effects 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- 210000002858 crystal cell Anatomy 0.000 description 6
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 4
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- AZYTZQYCOBXDGY-UHFFFAOYSA-N 2-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=CC=N1 AZYTZQYCOBXDGY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- XIIIHRLCKLSYNH-UHFFFAOYSA-N 4-Hexyloxyphenol Chemical compound CCCCCCOC1=CC=C(O)C=C1 XIIIHRLCKLSYNH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UTIMESSLYFMSPO-UHFFFAOYSA-N 2-methylbutyl 3-[4-[(4-decoxyphenyl)methylideneamino]phenyl]prop-2-enoate Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C=NC1=CC=C(C=CC(=O)OCC(C)CC)C=C1 UTIMESSLYFMSPO-UHFFFAOYSA-N 0.000 description 1
- PGFNVWGMBZSAEW-ZDUSSCGKSA-N 4-[(6s)-6-methyloctoxy]benzoic acid Chemical compound CC[C@H](C)CCCCCOC1=CC=C(C(O)=O)C=C1 PGFNVWGMBZSAEW-ZDUSSCGKSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- NEHMKBQYUWJMIP-DICFDUPASA-N chloro(dideuterio)methane Chemical compound [2H]C([2H])Cl NEHMKBQYUWJMIP-DICFDUPASA-N 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は強誘電性液晶化合物として有用な、光学活性な
アルコキシ安息香酸アルコキシまたはアルキルフェニル
エステル化合物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an optically active alkoxy or alkylphenyl ester compound of alkoxybenzoate useful as a ferroelectric liquid crystal compound.
液晶表示素子の表示方式として現在広く実用化されてい
るものは、ねじれネマチック（ＴＮ型）および動的散乱
型（ＤＳ型）である、これらはネマチック液晶を主成分
としたネマチック液晶セルによる表示である。従来のネ
マチック液晶セルの短所のひとつに、応答速度が遅く、
たかだか数ｍ秒のオーダーの応答速度しか得られないと
いう事実があげられ、このことがネマチック液晶セルの
応用範囲をせばめる一因となっている。しかし、最近に
到ってスメクチック液晶セルを用いれば、より高度な応
答が得られるということがわかってきた。The currently widely used display systems for liquid crystal display elements are twisted nematic (TN type) and dynamic scattering type (DS type), which are displays using nematic liquid crystal cells that mainly contain nematic liquid crystal. be. One of the disadvantages of conventional nematic liquid crystal cells is slow response speed.
The fact that a response speed on the order of several milliseconds can be obtained at most is one of the factors that limits the range of applications of nematic liquid crystal cells. However, it has recently been found that a more sophisticated response can be obtained by using a smectic liquid crystal cell.
光学活性なスメクチック液晶の中には、強誘電性を示す
ものがあることが明らかになってきており、その利用に
関して大きな期待が寄せられつつある０強誘電性を示す
液晶すなわち強誘電性液晶としては、例えば、４− （
４−ｎ−デシルオキシベンジリデンアミノ）ケイ皮酸−
２−メチルブチルエステル（以下、ＤＯＢＡＭＢＣと略
記する。）が知られており、そのカイラルスメクチック
相（以下、ＳＣ＊相と略記する。）において、強誘電性
を示すことを特徴とするものである。It has become clear that some optically active smectic liquid crystals exhibit ferroelectric properties, and there are great expectations for their use. For example, 4-(
4-n-decyloxybenzylidene amino)cinnamic acid-
2-Methylbutyl ester (hereinafter abbreviated as DOBAMBC) is known, and is characterized by exhibiting ferroelectricity in its chiral smectic phase (hereinafter abbreviated as SC* phase). .
近年、ＤＯＢＡＭＢＣの薄膜セルにおいて、８秒オーダ
ーの高速応答性が見出されたことを契機に、強誘電性液
晶はその高速応答性を利用して液晶テレビ等のディスプ
レイ用のみならず、光プリンターヘッド、光フーリエ変
換素子、ライトパルプ等のオプトエレクトロニクス関連
素子の素材用にも使用可能な材料として注目を集めてい
る。In recent years, with the discovery of high-speed response on the order of 8 seconds in DOBAMBC's thin film cells, ferroelectric liquid crystals have been used not only for displays such as LCD televisions but also for optical printers. It is attracting attention as a material that can be used for optoelectronic devices such as heads, optical Fourier transform devices, and light pulp.
しかし、ＤＯＢＡＭＢＣはシッフ塩基を含むため化学的
に不安定であり実用に供するに到っていない。However, since DOBAMBC contains a Schiff base, it is chemically unstable and has not been put to practical use.
本発明の目的は以上の様な用途に使用し得る新規な光学
活性を有する化合物を提供することである。An object of the present invention is to provide a compound having novel optical activity that can be used for the above-mentioned purposes.
即ち、本発明は次の一般式で表される化合物を提供する
ものである。That is, the present invention provides a compound represented by the following general formula.
（式中、Ｒ，は水素原子または炭素原子数１ないしｌＯ
の直鎖アルキル基を示し、Ｘは水素原子または塩素原子
を示し、Ｒ３は炭素原子数１〜１８の直鎖アルキル基を
示し、ｍは３〜６を示し、ｎは０またはｌを示し、＊は
不斉炭素原子を示す。但し、Ｒ５及びＸが共に水素原子
であることはない、）以下、上記要旨をもってなる本発
明について更に詳細に説明する。(In the formula, R is a hydrogen atom or a carbon atom number of 1 to 10
represents a straight chain alkyl group, X represents a hydrogen atom or a chlorine atom, R3 represents a straight chain alkyl group having 1 to 18 carbon atoms, m represents 3 to 6, n represents 0 or l, * indicates an asymmetric carbon atom. However, R5 and X are not both hydrogen atoms.) The present invention having the above-mentioned summary will be explained in more detail below.
上記一般式で表される化合物は、例えば、４位に光学活
性なアルコキシ置換基を有する安息香酸と４−ｎ−アル
キルまたはアルコキシフェノールとを反応させる等の周
知のエステル化反応により、容易に合成することができ
る。The compound represented by the above general formula can be easily synthesized by a well-known esterification reaction such as reacting benzoic acid having an optically active alkoxy substituent at the 4-position with 4-n-alkyl or alkoxyphenol. can do.
かくして得られる本発明の上記一般式で表される化合物
は、Ｓｃ”相及び又はカイラルネマチック相（以下、Ｎ
″と略記する）を有しており、液晶材料として単独で使
用できる他、他の液晶化合物と混合して、液晶組成物の
一成分として用いることもできる。The compound represented by the above general formula of the present invention thus obtained has a Sc" phase and/or a chiral nematic phase (hereinafter, N
In addition to being able to be used alone as a liquid crystal material, it can also be mixed with other liquid crystal compounds and used as a component of a liquid crystal composition.
次に、本発明を実施例によって説明する。しかしながら
、本発明はこれら実施例によって限定されるものではな
い。Next, the present invention will be explained by examples. However, the present invention is not limited to these examples.
実施例１
〔α〕。−＋５．００＠（２５℃、Ｃ＝１、ＣＨＣｌ３
溶液）の（Ｒ） −４−（６”−クロロ−４゛−メチル
へキシロキシ）安息香酸１．３ｇ、 ４−ｎ−オクチル
フェノール１．０ｇ５Ｎ。Example 1 [α]. -+5.00@(25℃, C=1, CHCl3
solution) of (R)-4-(6''-chloro-4'-methylhexyloxy)benzoic acid 1.3 g, 4-n-octylphenol 1.0 g 5N.
Ｎ−ジシクロへキシルカルボジイミド１．１ｇ、４−ピ
ロリジノピリジン０．１ｇ及びジクロルメタン１５１ｉ
をとり、室温で３時間撹拌した。その後、ｎ−ヘキサン
３０１ｄを加え、室温で１０分間撹拌した。析出したジ
シクロヘキシル尿素をろ別し、ろ液を脱溶媒した。得ら
れた粗生成物をｎ−ヘキサン／ジエチルエーテル（９／
１）を展開溶媒として、シリカゲルカラムを用いて精製
した後エタノールから再結晶し、目的の（Ｒ） −４−
（６°−クロロ−４°−メチルへキシロキシ）安息香酸
−４−ｎ−オクチルフェニルエステルを得た。1.1 g of N-dicyclohexylcarbodiimide, 0.1 g of 4-pyrrolidinopyridine and 151i of dichloromethane
The solution was stirred at room temperature for 3 hours. Then, 301d of n-hexane was added and stirred at room temperature for 10 minutes. The precipitated dicyclohexylurea was filtered off, and the filtrate was desolvented. The obtained crude product was mixed with n-hexane/diethyl ether (9/
1) as a developing solvent and purified using a silica gel column, then recrystallized from ethanol to obtain the desired (R) -4-
(6°-chloro-4°-methylhexyloxy)benzoic acid-4-n-octylphenyl ester was obtained.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０５０ｃｍ−’ （ｖｗ）、 ２９００ｃｍ−’
（ｓ）、 ２８５０ｃｍ−’ （＋ｓ）、１７２０ｃ
ｍ−’ （ｖｓ）、 １６１０ｃｍ−’ （ｓ）、
１５１０ｃｍ−’ （ｓ）、１４６０ｃ ｃ凰 （ｍ
） 、 １２５０ｃｍ−’ （ｖｓ） 、 １２００ｃ
ｍ−’ （ｓ） 、１１６０ｃｍ−’（ｖｓ）、 １
０８１０８Ｏ’ （ｓ）、 ７２０ｃｍ−’ （
ｍ）また、得られた生成物の旋光度を次に示す。3050cm-' (vw), 2900cm-'
(s), 2850cm-' (+s), 1720c
m-' (vs), 1610cm-' (s),
1510cm-' (s), 1460c c 凰 (m
), 1250cm-' (vs), 1200c
m-' (s), 1160 cm-' (vs), 1
08108O' (s), 720cm-' (
m) Also, the optical rotation of the obtained product is shown below.
〔α〕Ｄ冨＋３．２１° （２５℃、Ｃ・１、ＣｌＣｌ
、溶液）この化合物を二枚のガラス板間に挟み、偏光顕
微鏡による相形態観察を行った結果、以下の相転移を確
認した。[α]D depth +3.21° (25℃, C・1, ClCl
, solution) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
実施例２
〔α〕。・＋８．０７° （２５℃、Ｃ−１、ＣＨＣｌ
５溶液）の（Ｒ）−４−（６°−クロロ−４”−メチル
オクトキシ）安息香酸１．５ｇ、 ４−ｎ−オクチルフ
ェノール１．０ｇ５Ｎ、Ｎ−ジシクロへキシルカルボジ
イミド１．１ｇ、４−ピロリジノピリジン０．１ｇ及び
ジクロルメタン２０ｄをとり、室温で３時間撹拌した。Example 2 [α].・+8.07° (25°C, C-1, CHCl
5 solution) of (R)-4-(6°-chloro-4''-methyloctoxy)benzoic acid 1.5 g, 4-n-octylphenol 1.0 g 5N, N-dicyclohexylcarbodiimide 1.1 g, 4- 0.1 g of pyrrolidinopyridine and 20 d of dichloromethane were taken and stirred at room temperature for 3 hours.
析出したジシクロヘキシル尿素をろ別し、ろ液を脱溶媒
した。得られた粗生成物を、ｎ−ヘキサン／ジエチルエ
ーテル（９３／７）を展開溶媒として、シリカゲルカラ
ムを用いて精製し、目的の（Ｒ） −４−（６’−クロ
ロ−４′−メチルオクトキシ）安息香酸−４−ｎ−オク
チルフェニルエステルを得た。The precipitated dicyclohexylurea was filtered off, and the filtrate was desolvented. The obtained crude product was purified using a silica gel column using n-hexane/diethyl ether (93/7) as a developing solvent to obtain the desired (R)-4-(6'-chloro-4'-methyl 4-n-octylphenyl octoxybenzoic acid ester was obtained.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０５０ｃｍ−’ （ｖｗ）、２９５０ｃｍ＋−’ （
ｓ）、２８７５ｃｍ−’ （ｍ）、１７３５ｃｍ−’
（ｓ）、１６１０ｃｎ＋−’ （ｓ）、１５８５ｃｍ−
’ （ｗ）、１５１５ｃｍ−’ （ｓ）、１４６５ｃ
ｎ＋−’ 軸）、１２６０ｃ＋ｓ−’ （ｖｓ）、１
２０５ｃｍ−’ （ｓ）、１１７５ｃ＋ｗ−’ （ｖｓ
）、１０７５ｃｍ−’ （ｓ）、１０２０ｃ＋＋＋−’
（ｓ）
また、得られた生成物の旋光度を次に示す。3050cm-' (vw), 2950cm+-' (
s), 2875cm-' (m), 1735cm-'
(s), 1610cn+-' (s), 1585cm-
' (w), 1515cm-' (s), 1465c
n+-' axis), 1260c+s-' (vs), 1
205cm-' (s), 1175c+w-' (vs
), 1075cm-' (s), 1020c+++-'
(s) Also, the optical rotation of the obtained product is shown below.
〔α〕。・＋５．４１″′（２５°Ｃ，Ｃ＝１、ＣＨＣ
ｌ３溶液）この化合物を二枚のガラス板間に挟み、偏光
顕微鏡による相形態観察を行った結果、以下の相転移を
確認した。[α].・+5.41″' (25°C, C=1, CHC
(13 solution) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
実施例３
〔α） ｏ ＝ ＋３．３７０ （２３℃、Ｃ＝１、Ｃ
Ｉ（Ｃ１３溶液）の（Ｒ） −４−（６’−クロロ−４
”−メチルノニロキシ）安息香酸１．６ｇ、 ４−ｎ−
へキシロキシフェノール１．０ ｇ 。Example 3 [α) o = +3.370 (23°C, C=1, C
(R)-4-(6'-chloro-4 of I (C13 solution)
"-Methylnonyloxy)benzoic acid 1.6 g, 4-n-
Hexyloxyphenol 1.0 g.
Ｎ、Ｎ−ジシクロへキシルカルボジイミド１．１ｇ、４
−ピロリジノピリジン０．１ｇ及びジクロルメタン２０
ｄをとり、室温で３時間撹拌した。析出したジシクロヘ
キシル尿素をろ別し、ろ液を脱溶媒した。N,N-dicyclohexylcarbodiimide 1.1g, 4
- 0.1 g of pyrrolidinopyridine and 20 g of dichloromethane
d was taken and stirred at room temperature for 3 hours. The precipitated dicyclohexylurea was filtered off, and the filtrate was desolvented.
得られた粗生成物を、ｎ−ヘキサン、／ジエチルエーテ
ル（９３／７）を展開溶媒として、シリカゲルカラムを
用いて精製し、目的の（Ｒ） −４−（６”−クロロ−
４゛−メチルノニロキシ）安息香酸−４−ｎ−へキシロ
キシフェニルエステルを得た。The obtained crude product was purified using a silica gel column using n-hexane/diethyl ether (93/7) as a developing solvent to obtain the desired (R)-4-(6''-chloro-
4'-Methylnonyloxy)benzoic acid-4-n-hexyloxyphenyl ester was obtained.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０５０ｃｍ−’ （ｖｗ）、 ２９５０ｃｍ−’
（ｓ）、 ２８５０ｃｍ−’ （ｓ＋）、１７２０ｃ
ｍ＋−’ （ｓ）、 １６００ｃｍ−’ （ｓ）、
１５００ｃｍ−’ （ｓ）、１４６０ｃｍ−’ （
ｍ）、１２５０ｃｎ＋−’ （ｓ）、１２００ｃａ＋−
’ （ｓ）、１１６０ｃｍ−’ （ｓ）、１０７１０
７Ｏ’ （ｓ）また、得られた生成物の旋光度を次に
示す。3050cm-' (vw), 2950cm-'
(s), 2850cm-' (s+), 1720c
m+-' (s), 1600cm-' (s),
1500cm-' (s), 1460cm-' (
m), 1250cn+-' (s), 1200ca+-
' (s), 1160cm-' (s), 10710
7O' (s) Also, the optical rotation of the obtained product is shown below.
〔α〕。＝ ＋２．５６° （２３°Ｃ，Ｃ・１、Ｃｌ
ＩＣ１ｉ溶液）この化合物を、ラビングにより配向処理
を施した厚さ２μｍのガラス透明電極セルに注入した後
５０°Ｃに加熱して等方性液体とした。[α]. = +2.56° (23°C, C・1, Cl
IC1i solution) This compound was injected into a glass transparent electrode cell with a thickness of 2 μm that had been subjected to an alignment treatment by rubbing, and then heated to 50° C. to form an isotropic liquid.
この液晶セルを直交ニコル下で±１５Ｖ、ＩＨｚの矩形
波を印加しながら冷却すると、１２．５°Ｃ以下で明瞭
なスイッチング動作が確認された。When this liquid crystal cell was cooled under crossed Nicol conditions while applying a ±15 V, IHz square wave, a clear switching operation was confirmed below 12.5°C.
また、偏光顕微鏡により相形態観察を行い、以下の相転
移を確認した。In addition, the phase morphology was observed using a polarizing microscope, and the following phase transition was confirmed.
実施例４
（Ｓ） −４−（４’−メチルへブチロキシ）安息香酸
１．２ｇ、４−ｎ−オクチルフェノール１．０ｇ、 Ｎ
、Ｎ−ジシクロへキシルカルボジイミド１．１ｇ、４−
ピロリジノピリジン０．１ｇ及びジクロルメタン１５Ｍ
１をとり、室温で３時間撹拌した。その後、ｎ−ヘキサ
ン３０ｉ１！１！を加え、室温で１０分間撹拌した。析
出したジシクロヘキシル尿素をろ別し、ろ液を脱溶媒し
た。得られた粗生成物をｎ−ヘキサン／ジエチルエーテ
ル（９６／４）を展開溶媒として、シリカゲルカラムを
用いて精製した後メタノールから再結晶し、目的の（Ｓ
）−４−（４’−メチルへブチロキシ）安息香酸−４−
〇−オクチルフェニルエステルを得た。Example 4 (S) -4-(4'-methylhebutyloxy)benzoic acid 1.2 g, 4-n-octylphenol 1.0 g, N
, N-dicyclohexylcarbodiimide 1.1g, 4-
0.1g of pyrrolidinopyridine and 15M of dichloromethane
1 was taken and stirred at room temperature for 3 hours. Then n-hexane 30i1!1! was added and stirred at room temperature for 10 minutes. The precipitated dicyclohexylurea was filtered off, and the filtrate was desolvented. The obtained crude product was purified using a silica gel column using n-hexane/diethyl ether (96/4) as a developing solvent, and then recrystallized from methanol to obtain the desired (S
)-4-(4'-methylhebutyloxy)benzoic acid-4-
〇-octylphenyl ester was obtained.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０２０ｃｍ−’ （ｖｗ）、２９００ｃｍ−’ （ｓ
）、２８４０ｃｍリ （ｎ＋）、１７２０ｃｍ−’ （
ｓ）、１６００ｃ＋ｗ−’ （ｓ）、１５００ｃｍ−’
（ｓ）、１４６０ｃｍ−’ （ｍ）、 １２５０ｃ
ｍ−’ （ｖｓ）、 １２００ｃｍ＋−’ （ｓ）、
１１６０ｃｍ−’ （ｖｓ）、１０７１０７Ｏ’ （ｍ
）また、得られた生成物の旋光度を次に示す。3020cm-' (vw), 2900cm-' (s
), 2840cmli (n+), 1720cm-' (
s), 1600c+w-' (s), 1500cm-'
(s), 1460cm-' (m), 1250c
m-' (vs), 1200cm+-' (s),
1160cm-' (vs), 107107O' (m
) Also, the optical rotation of the obtained product is shown below.
〔α］。・＋１．４９° （２５°Ｃ，Ｃ＝ｔ、ＣＨＣ
ｌ３溶液）この化合物を二枚のガラス板間に挟み、偏光
顕微鏡による相形態観察を行った結果、以下の相転移を
確認した。[α].・+1.49° (25°C, C=t, CHC
(13 solution) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
実施例５
４−ｎ−オクチルフェノールに代えて４−ｎ−へキシロ
キシフェノールを用いる他は実施例４と同様の操作によ
り、標記の化合物を合成した。Example 5 The title compound was synthesized in the same manner as in Example 4, except that 4-n-hexyloxyphenol was used in place of 4-n-octylphenol.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０５０ｃｍ−’ （ｖｗ）、２９００ｃ＋ｓ−’ （
ｓ）、２８５０ｃｍ−’ （ｍ）、１７２０ｃｎ−’
（ｓ）、１６００ｃｍ−’ （ｓ）、１５００ｃｍ−’
（ｓ）、１４７０ｃ＋＋＋−’ （ｍ）、１２５０ｃ
ｍ−’ （ｖｓ）、１２００ｃｍ−’ （ｓ）、１１７
０ｃｍ−’ （ｓ）、１０８０ｃｓ＋−’ （ｓ）また
、得られた生成物の旋光度を次に示す。3050cm-' (vw), 2900c+s-' (
s), 2850cm-' (m), 1720cn-'
(s), 1600cm-' (s), 1500cm-'
(s), 1470c+++-' (m), 1250c
m-' (vs), 1200cm-' (s), 117
0 cm-' (s), 1080 cs+-' (s) Also, the optical rotation of the obtained product is shown below.
〔α〕。・＋１．５０’ （２５℃、Ｃ＝１、ＣＩ（
Ｃ１ｉ溶液）この化合物を二枚のガラス板間に挟み、偏
光顕微鏡による相形態観察を行った結果、以下の相転移
を確認した。[α].・+1.50' (25℃, C=1, CI(
C1i solution) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
実施例６
（Ｓ） −４−（４°−メチルへブチロキシ）安息香酸
に代えて、（Ｓ）−４−（５°−メチルオクトキシ）安
息香酸を用いる他は実施例４と同様の操作により、標記
の化合物を合成した。Example 6 The same procedure as in Example 4 except that (S)-4-(5°-methyloctoxy)benzoic acid was used instead of (S)-4-(4°-methylhebutyloxy)benzoic acid. The title compound was synthesized.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０３０ｃｍ−’ （ｖｗ）、２９５０ｃ＋ｍ−’ （
ｓ）、２８５０ｃｍ−’ （ｍ）、１７３０ｃｍ−’
（ｓ）、１６００ｃ＋＊−’ （ｓ）、１５１０ｃｍ−
’ （ｓ）、１４６０ｃｍ−’ （ｍ）、１２５０ｃｓ
ｅ−’ （ｖｓ）、１２００ｃ＋ｗ−’ （ｓ）、１１
７０ｃｍ−’ （ｓ）、 １０７０ｃｍ＋−’ 軸
）また、得られた生成物の旋光度を次に示す。3030cm-' (vw), 2950c+m-' (
s), 2850cm-' (m), 1730cm-'
(s), 1600c+*-' (s), 1510cm-
' (s), 1460cm-' (m), 1250cs
e-' (vs), 1200c+w-' (s), 11
70 cm-' (s), 1070 cm+-' axis) Also, the optical rotation of the obtained product is shown below.
〔α〕。・＋０．５９＠（２５℃、Ｃ＝１、ＣｌＣｌ！
ｌＣｌ−の化合物を二枚のガラス板間に挟み、偏光顕微
鏡による相形態観察を行った結果、以下の相転移を確認
した。[α].・+0.59@(25℃, C=1, ClCl!
A lCl- compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
実施例７
（Ｓ）−４−（４’−メチルへブチロキシ）安息香酸に
代えて、（Ｓ） −４−（６’−メチルオクトキシ）安
息香酸を用いる他は実施例４と同様の操作により、標記
の化合物を合成した。Example 7 The same procedure as in Example 4 except that (S)-4-(6'-methyloctoxy)benzoic acid was used instead of (S)-4-(4'-methylhebutyloxy)benzoic acid. The title compound was synthesized.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０００ｃｍ−’ （ｖｗ）、 ２９００ｃｍ＋−’
、（ｓ）、 ２８５０ｃｍ−鳳 （ｍ）、１７３０
ｃｍ−’ （ｓ）、１６００ｃｍ−’ 軸）、１５００
ｃｍ−’ Ｃ＋＋）、１４６０ｃｍ−’ （ｍ）、
１２５０ｃｍ−’ （ｓ）、 １２００ｃｍ−’
（ＩＩ＋）、１１６０ｃｍ−’ （ｓ）、 １０７１
０７Ｏ’ （ｍ）また、得られた生成物の旋光度を次
に示す。3000cm-' (vw), 2900cm+-'
, (s), 2850cm-Otori (m), 1730
cm-' (s), 1600 cm-' axis), 1500
cm-' C++), 1460 cm-' (m),
1250cm-' (s), 1200cm-'
(II+), 1160cm-' (s), 1071
07O' (m) Also, the optical rotation of the obtained product is shown below.
（α） ｎ −＋０．９１° （２５℃、Ｃ，１、ＣＨ
Ｃｈ溶液）この化合物を、ラビングにより配向処理を施
した厚さ２μｍのガラス透明電極セルに注入した後７０
℃に加熱して等方性液体とした。(α) n −+0.91° (25°C, C, 1, CH
Ch solution) After injecting this compound into a glass transparent electrode cell with a thickness of 2 μm that had been subjected to an alignment treatment by rubbing,
It was heated to ℃ to make it an isotropic liquid.
この液晶セルを直交ニコル下で±１５Ｖ、ＩＨｚの矩形
波を印加しながら冷却すると、３６．５〜−５°Ｃの間
で明瞭なスイッチング動作が確認された。When this liquid crystal cell was cooled under crossed Nicol conditions while applying a ±15 V, IHz square wave, a clear switching operation was confirmed between 36.5 and -5°C.
また、偏光顕微鏡により相形態観察を行い、以下の相転
移を確認した。In addition, the phase morphology was observed using a polarizing microscope, and the following phase transition was confirmed.
Claims (1)
０の直鎖アルキル基を示し、Ｘは水素原子または塩素原
子を示し、Ｒ＿２は炭素原子数１〜１８の直鎖アルキル
基を示し、ｍは３〜６を示し、ｎは０または１を示し、
＊は不斉炭素原子を示す、但し、Ｒ＿１及びＸが共に水
素原子であることはない。）[Claims] An optically active ester compound represented by the following general formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 is a hydrogen atom or 1 or 1 carbon atom.
0 represents a straight chain alkyl group, X represents a hydrogen atom or a chlorine atom, R_2 represents a straight chain alkyl group having 1 to 18 carbon atoms, m represents 3 to 6, and n represents 0 or 1. ,
* indicates an asymmetric carbon atom, provided that R_1 and X are not both hydrogen atoms. )
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62130293A JPH0784417B2 (en) | 1987-05-27 | 1987-05-27 | Optically active ester compound |
| US07/164,878 US4866199A (en) | 1987-03-20 | 1988-03-08 | Optically active ester compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62130293A JPH0784417B2 (en) | 1987-05-27 | 1987-05-27 | Optically active ester compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63295534A true JPS63295534A (en) | 1988-12-01 |
| JPH0784417B2 JPH0784417B2 (en) | 1995-09-13 |
Family
ID=15030849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62130293A Expired - Lifetime JPH0784417B2 (en) | 1987-03-20 | 1987-05-27 | Optically active ester compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0784417B2 (en) |
-
1987
- 1987-05-27 JP JP62130293A patent/JPH0784417B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0784417B2 (en) | 1995-09-13 |
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