JPS63190839A - Optically active alcohol compound - Google Patents
Optically active alcohol compoundInfo
- Publication number
- JPS63190839A JPS63190839A JP2378587A JP2378587A JPS63190839A JP S63190839 A JPS63190839 A JP S63190839A JP 2378587 A JP2378587 A JP 2378587A JP 2378587 A JP2378587 A JP 2378587A JP S63190839 A JPS63190839 A JP S63190839A
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- optically active
- compound
- give
- reduced
- 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 alcohol compound Chemical class 0.000 title claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 230000003287 optical effect Effects 0.000 abstract description 5
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 4
- 230000002152 alkylating effect Effects 0.000 abstract description 3
- 239000003317 industrial substance Substances 0.000 abstract description 3
- 238000011914 asymmetric synthesis Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 abstract description 2
- 229930003633 citronellal Natural products 0.000 abstract description 2
- 235000000983 citronellal Nutrition 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 230000001766 physiological effect Effects 0.000 abstract description 2
- GJWSUKYXUMVMGX-UHFFFAOYSA-N (+)-(R)-citronellic acid Natural products OC(=O)CC(C)CCC=C(C)C GJWSUKYXUMVMGX-UHFFFAOYSA-N 0.000 abstract 2
- GJWSUKYXUMVMGX-SECBINFHSA-N (R)-citronellic acid Chemical compound OC(=O)C[C@H](C)CCC=C(C)C GJWSUKYXUMVMGX-SECBINFHSA-N 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NZOFMZZOPRFZFQ-UHFFFAOYSA-N 6-chloro-4-methylnonan-1-ol Chemical compound CCCC(Cl)CC(C)CCCO NZOFMZZOPRFZFQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DLQHGKLSSXKYGH-UHFFFAOYSA-N 6-chloro-4-methylhexan-1-ol Chemical compound ClCCC(C)CCCO DLQHGKLSSXKYGH-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000156978 Erebia Species 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本発明は特定の光学活性アルコール化合物に関し、詳し
くは、不斉炭素を存する４−メチル−６−クロロアルカ
ノール化合物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a specific optically active alcohol compound, and more particularly to a 4-methyl-6-chloroalkanol compound containing an asymmetric carbon.
メチル分岐を有するアルコール化合物は、化粧品、医薬
の中間原料等の種々の工業薬品として有用であり、特に
、光学活性アルコール化合物は、液晶化学物質用中間体
として近年特に注目を集めている。例えば、アルコキシ
フェニルピリミジン化合物、アルコキシ安息香酸誘導体
等は強誘電性スメクチ・７り液晶化学物質として知られ
ている。Alcohol compounds having a methyl branch are useful as various industrial chemicals such as intermediate raw materials for cosmetics and pharmaceuticals, and in particular, optically active alcohol compounds have recently attracted particular attention as intermediates for liquid crystal chemicals. For example, alkoxyphenylpyrimidine compounds, alkoxybenzoic acid derivatives, and the like are known as ferroelectric liquid crystal chemical substances.
これらの液晶化合物におけるアルコキシ基としては、２
−メチルブトキシあるいは６−メチルオクトキシ等の比
較的炭素数の小さいアルコールがら誘導されるアルコキ
シ基が知られているが、これらの化合物は使用可能温度
範囲が適切でない等の問題を有しており、実用上満足し
えるものではなかった。The alkoxy group in these liquid crystal compounds is 2
- Alkoxy groups derived from alcohols with a relatively small number of carbon atoms such as methylbutoxy or 6-methyloctoxy are known, but these compounds have problems such as an inappropriate usable temperature range. , which was not practically satisfactory.
本発明者等は、メチル分岐を有する光学活性アルコール
化合物について検討を重ねた結果、次の−ｍ式（Ｉ）で
表される化合物が優れた光学活性を有していることを見
出した。As a result of repeated studies on optically active alcohol compounds having a methyl branch, the present inventors found that a compound represented by the following -m formula (I) has excellent optical activity.
ＨＯ（ＣＨｚ）：＋ ＣＨＣＨｚ−Ｃ１ｌ Ｒ（１）
ＣＨ，ｃ＋
（式中、Ｒは水素原子または炭素原子数１〜１８の直鎖
アルキル基を示し、＊は不斉炭素を示す。）本発明の光
学活性アルコールは、工業薬品として重要な物質である
。例えば、上記の液晶化合物用の中間体以外にも、光学
分割剤あるいは不斉合成の助剤として有用であり、また
種々の生理活性も期待される。HO (CHz): + CHCHz-C1l R(1)
CH, c+ (In the formula, R represents a hydrogen atom or a linear alkyl group having 1 to 18 carbon atoms, and * represents an asymmetric carbon.) The optically active alcohol of the present invention is an important substance as an industrial chemical. be. For example, in addition to the above intermediates for liquid crystal compounds, they are useful as optical resolution agents or auxiliary agents for asymmetric synthesis, and are also expected to have various physiological activities.
以下本発明について更に詳細に説明する。The present invention will be explained in more detail below.
Ｒで示されるアルキル基としては、メチル、エチル、プ
ロピル、ブチル、ペンチル、ヘキシル、ヘプチル、オク
チル、ノニル、デシル、ウンデシル、ドデシル、トリデ
シル、テトラデシル、ヘキサデシル及びオクタデシル基
があげられる。Examples of the alkyl group represented by R include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl and octadecyl groups.
従って、上記一般式（１）で表される化合物としては、
６−クロロ−４−メチルヘキサノール、６−クロロ−４
−メチルオクタツール、６−クロロ−４−メチルノナノ
ール、６−クロロ−４−メチルデカノール、６−クロロ
−４−メチルドデカノール、６−クロロ−４−メチルオ
クタデカノール等があげられる。Therefore, as a compound represented by the above general formula (1),
6-chloro-4-methylhexanol, 6-chloro-4
-Methyloctatool, 6-chloro-4-methylnonanol, 6-chloro-4-methyldecanol, 6-chloro-4-methyldodecanol, 6-chloro-4-methyloctadecanol, and the like.
これらの化合物は、例えば、（Ｒ）−（Ｉ）−シトロネ
ル酸またはこれをアルキル化することによって得られる
（Ｒ） −２，６−シメチルー８−オキソアルケン−２
を還元する方法、あるいは光学活性な３．７−ジメチル
−６−オクテナールまたはこれをアルキル化することに
よって得られる光学活性な２．６−シメチルー８−オキ
ソアルケン−２を還元する方法によって得られる光学活
性な２．６−シメチルー８−ヒドロキシアルケン−２を
クロル化して２，６−シメチルー８−クロロアルケン−
２を製造し、次いで酸化、還元することによって製造す
ることができる。These compounds are, for example, (R)-(I)-citronel acid or (R)-2,6-dimethyl-8-oxoalkene-2 obtained by alkylating it.
or optically active 3,7-dimethyl-6-octenal or optically active 2,6-dimethyl-8-oxoalkene-2 obtained by alkylating it. Active 2,6-dimethyl-8-hydroxyalkene-2 is chlorinated to form 2,6-dimethyl-8-chloroalkene-2.
It can be produced by producing 2, followed by oxidation and reduction.
以下、本発明を実施例によって具体的に説明する。しか
し、本発明はこれらの実施例によって制限されるもので
はない。Hereinafter, the present invention will be specifically explained with reference to Examples. However, the present invention is not limited to these examples.
実施例１
■二叉ユ旦ニ↓二り土盈オえ叉Ｊ二ｙ■査戊（１１２，
６−シメチルー８−ヒドロキシデセン−２の合成１８．
２ ｇの光学活性な２，６−シメチルー８−オキソデセ
ン−２をエタノール５０ｍ７に？容解し、室７品で１９
ｇの水素化ホウ素ナトリウムを５分を要して加えた後、
室温で２時間攪拌した。Example 1 ■ Two-pronged Yutan ↓ Two-pronged Earth Oe-sha J2y ■ Examination (112,
Synthesis of 6-dimethyl-8-hydroxydecene-2 18.
2 g of optically active 2,6-dimethyl-8-oxodecene-2 in 50 m7 of ethanol? Comprehensive, 19 in 7 dishes
After adding g of sodium borohydride over 5 minutes,
The mixture was stirred at room temperature for 2 hours.
反応混合物を充分に濃縮後、５０ｕ／の水を加え、ジエ
チルエーテルで抽出し、飽和食塩水で洗浄後乾燥した。After sufficiently concentrating the reaction mixture, 50 u/h of water was added, extracted with diethyl ether, washed with saturated brine, and dried.
溶媒を溜去した後蒸溜し、沸点７９〜８０”ｃ ／ １
ｍｍ１１ｇの溜升として１５．５ ｇの２．６−シメ
チルー８−ヒドロキシデセン−２を得た。Distilled after removing the solvent, boiling point 79-80"c/1
15.5 g of 2.6-dimethyl-8-hydroxydecene-2 was obtained as a distillate of 11 g mm.
（２）２ 、６−シメチルー８−クロロデセン−２の合
成１３．８ ｇの２．６−シメチルー８−ヒドロキシデ
セン−２を７５ＤＩ７の四塩化炭素に溶解し、トリフェ
ニルホスフィン２１．０ ｇを加え、還流下に３時間攪
拌した。(2) Synthesis of 2,6-dimethyl-8-chlorodecene-2 13.8 g of 2,6-dimethyl-8-hydroxydecene-2 was dissolved in 75DI7 carbon tetrachloride, and 21.0 g of triphenylphosphine was added. , and stirred under reflux for 3 hours.
溶媒を溜去した後ヘキサンで抽出し、ヘキサンを溜去し
た後蒸溜し、沸点１１８〜１２０℃／１６ａ＋ｍＨｇの
溜升として６６９ｇの２．６−シメチルー８−クロロデ
セン−２を得た。After the solvent was distilled off, the mixture was extracted with hexane, and after the hexane was distilled off, it was distilled to obtain 669 g of 2.6-dimethyl-8-chlorodecene-2 as a distillate with a boiling point of 118-120°C/16a+mHg.
（３）６−クロロ−４−メチルオクタツールの合成無水
メタノール及び無水ジクロロメタン各１００−をとり、
ここに６．９ｇの２．６−シメチルー８−クロロデセン
−２を溶解した。これを−４０℃に冷却し０．０４ ｇ
／ ｌのオゾンを含有する酸素を１２０１７時間の速
度で３０分間吹き込んだ。窒素ガスを吹き込み過剰のオ
ゾンを除去した後、同温度で水素化ホウ素ナトリウム４
．２ｇを加え、１時間を要して室温まで昇温し、室温で
さらに１時間攪拌した。(3) Synthesis of 6-chloro-4-methyloctatool Take 100% each of anhydrous methanol and anhydrous dichloromethane,
6.9 g of 2,6-dimethyl-8-chlorodecene-2 was dissolved therein. Cool this to -40℃ and weigh 0.04 g
Oxygen containing 1/l of ozone was blown in for 30 minutes at a rate of 12017 hours. After removing excess ozone by blowing nitrogen gas, sodium borohydride 4 was added at the same temperature.
．． 2 g was added, the temperature was raised to room temperature over 1 hour, and the mixture was further stirred at room temperature for 1 hour.
−夜放置後、反応液にトルエン１００ｍ７を加え、５％
塩酸２００ｍ／中にあけ、室温で１時間攪拌した。-After standing overnight, add 100m7 of toluene to the reaction solution and add 5%
The mixture was poured into 200ml of hydrochloric acid and stirred at room temperature for 1 hour.
トルエン層をとり、飽和食塩水で洗浄した後乾燥した。The toluene layer was taken, washed with saturated brine, and then dried.
トルエンを溜去した後蒸溜し、沸点６９〜７０℃１０．
１１１Ｉｎ＋Ｈｇの溜升として、３．２ｇの目的物であ
る６−クロロ−４−メチルオクタツールを得た。After removing toluene, it is distilled to a boiling point of 69-70℃10.
3.2 g of the target product, 6-chloro-4-methyloctatool, was obtained as a distillate of 111In+Hg.
Ｉ Ｒ（ｃｓ＋−’）
３３２５ （ｓ）、２９００ （ｓ）、１４５５ （ｓ
）、１３８０ （ｍ）、１０５５ （ｓ）、６１０ （
ｍ）
Ｈ−Ｎ Ｍ Ｒ（ＣＣ１４）
６４．０３ （ｓ： ＩＩＩ、 ＯＨ）、３．８０ （
町１）１． Ｃ１１−ＣＩ）、３．４３ （ｔ、 Ｊ＝
６Ｈｚ；２１＋、 ＣＨｚ−０）、２．００〜１．０６
（ｍ； ９Ｈ，ＣＨ２及びＣＨ）、０．９６ （ｔ、
Ｊ、６１１□； ３ｔｌ、 Ｃ１ｌ＋）、０．８５
（ｄ、 Ｊ＝５Ｈｚ； ３１１． ＣＨ３）比旋光度
（α） Ｄ＝ ＋０．７５°（２８℃、Ｃ＝ １ 、
ＣｌｌＣｌ：ｌ溶液）実施例２
エニ３リョと−にノ」ソとＬ±ノ二ソリ針叙戊２．６−
シメチルー８−オキソデセン−２に代え、光学活性な２
．６−シメチルー８−オキソウンデセン−２を用いる他
は実施例１と全く同様の操作により、沸点７１〜７２℃
１０．１ ｍｍ１１ｇの溜升として目的物である、６−
クロロ−４−メチルノナノールを得た。I R(cs+-') 3325 (s), 2900 (s), 1455 (s
), 1380 (m), 1055 (s), 610 (
m) H-NMR (CC14) 64.03 (s: III, OH), 3.80 (
Town 1) 1. C11-CI), 3.43 (t, J=
6Hz; 21+, CHz-0), 2.00-1.06
(m; 9H, CH2 and CH), 0.96 (t,
J, 611□; 3tl, C1l+), 0.85
(d, J=5Hz; 311. CH3) Specific optical rotation (α) D= +0.75° (28°C, C=1,
CllCl:l solution) Example 2 Any 3 Ryo and - Ni no' So and L ± No 2 sori needle setting 2.6-
Instead of dimethyl-8-oxodecene-2, optically active 2
．． The boiling point was 71 to 72°C by the same procedure as in Example 1 except that 6-dimethyl-8-oxoundecene-2 was used.
The target object, 6-
Chloro-4-methylnonanol was obtained.
ｌ Ｒ（ｃｍ−’）
３３２５ （ｓ）、２９５０ （ｓ）、１４６０ （ｓ
）、１３８０ （ｍ）、１０６０ （ｓ）、６０５ （
ｍ）
ＦＩ −Ｎ Ｍ Ｒ（ＣＣ１，）
δ ４．００ Ｃｍ； １１． ＣＩ−ＣＩ）、３．５
８ （ｔ、 Ｊ＝６Ｈｚ； ２Ｈ，Ｃｌ１ｇ−０）、２
．７７ （ｂｒ−ｓ； ＩＩ（、０ｆｆ）、１．９３〜
１．１０ （ｍ； ＩＩＨ，Ｃ１ｂ及びＣ１１）、０．
９３ （ｔ、 ｄ＝６１１ｚ； ３Ｈ，Ｃ１１３）、０
．９２ （ｄ、 Ｊ・５Ｈｚ； ３ｔＬ Ｃ１ｌ：ｌ）
比旋光度
〔α〕 。−−１，７５° （２７℃、 Ｃ＝ ２
、ＣｌｌＣｌ：ｌ ン容液）実施例３
」−クロロ−４−メチルヘキサノール９合成２．６−シ
メチルー８−オキソデセン−２に代え、光学活性な３，
７−ジメチル−６−オクテナールを用いる他は実施例１
と全く同様の操作により標記の化合物を合成した。ただ
し、目的物は酢酸エチル／ｎ−ヘキサン（２５／７５）
を展開溶媒として、シリカゲルカラムクロマトグラフィ
ーにより精製した。l R(cm-') 3325 (s), 2950 (s), 1460 (s
), 1380 (m), 1060 (s), 605 (
m) FI -N M R (CC1,) δ 4.00 Cm; 11. CI-CI), 3.5
8 (t, J=6Hz; 2H, Cl1g-0), 2
．． 77 (br-s; II (,0ff), 1.93~
1.10 (m; IIH, C1b and C11), 0.
93 (t, d=611z; 3H, C113), 0
．． 92 (d, J・5Hz; 3tL C1l:l)
Specific optical rotation [α]. --1,75° (27℃, C=2
, CClCl:l) Example 3 -Chloro-4-methylhexanol 9 Synthesis 2.In place of 6-dimethyl-8-oxodecene-2, optically active 3,
Example 1 except that 7-dimethyl-6-octenal is used.
The title compound was synthesized in exactly the same manner as above. However, the target product is ethyl acetate/n-hexane (25/75)
The product was purified by silica gel column chromatography using as a developing solvent.
Ｔ Ｒ（ｃｍ−’）
３３４０ （ｓ）、２９２５ （ｓ）、１４５０ （ｓ
）、１３８０ （ｍ）、１０５５ （ｓ）、６５０ （
ｍ）
ＨＮ Ｍ Ｒ（ＣＣ１ａ）
６３．４５ （ｔ、 Ｊ＝６Ｈ，； ２＋１． ＣＨ２
−０）、３．４５ Ｄ、 Ｊ＝６１１□； ２Ｈ，Ｃ１
１ｚ−ＣＩ）、３．１３ （ｓ； Ｉｌｌ、 ０１ｌ）
、２．００〜１．１０ （ｍ； ＩＨ，Ｃ１ｌ□及びＣ
）ｌ）、０．８８ （ｄ、 Ｊ・５．５Ｈｚ： ３１１
． Ｃ１ｈ）比旋光度
〔α〕。＝−３，７６°（２７℃、Ｃ＝ ２ 、ＣＨＣ
ｌ３溶液）特許出願人 アデカ・アーガス化学株式会社
ＪソT R (cm-') 3340 (s), 2925 (s), 1450 (s
), 1380 (m), 1055 (s), 650 (
m) HN M R (CC1a) 63.45 (t, J=6H,; 2+1. CH2
-0), 3.45 D, J=611□; 2H, C1
1z-CI), 3.13 (s; Ill, 01l)
, 2.00-1.10 (m; IH, C1l□ and C
)l), 0.88 (d, J・5.5Hz: 311
．． C1h) Specific rotation [α]. =-3,76° (27°C, C=2, CHC
l3 solution) Patent applicant: ADEKA ARGUS CHEMICAL CO., LTD.
Claims (1)
物。 ▲数式、化学式、表等があります▼（ I ） （式中、Ｒは水素原子または炭素原子数１〜１８の直鎖
アルキル基を示し、＊は不斉炭素を示す。）[Claims] An optically active alcohol compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R represents a hydrogen atom or a straight-chain alkyl group having 1 to 18 carbon atoms, and * represents an asymmetric carbon.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2378587A JPH0660114B2 (en) | 1987-02-04 | 1987-02-04 | Optically active alcohol compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2378587A JPH0660114B2 (en) | 1987-02-04 | 1987-02-04 | Optically active alcohol compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63190839A true JPS63190839A (en) | 1988-08-08 |
| JPH0660114B2 JPH0660114B2 (en) | 1994-08-10 |
Family
ID=12119979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2378587A Expired - Fee Related JPH0660114B2 (en) | 1987-02-04 | 1987-02-04 | Optically active alcohol compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0660114B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5174080A (en) * | 1990-02-22 | 1992-12-29 | Shimizu Construction Co., Ltd. | Column and beam connecting assembly |
| US5218802A (en) * | 1990-01-16 | 1993-06-15 | Shimizu Construction Co., Ltd. | Column and beam connecting assembly |
-
1987
- 1987-02-04 JP JP2378587A patent/JPH0660114B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5218802A (en) * | 1990-01-16 | 1993-06-15 | Shimizu Construction Co., Ltd. | Column and beam connecting assembly |
| US5174080A (en) * | 1990-02-22 | 1992-12-29 | Shimizu Construction Co., Ltd. | Column and beam connecting assembly |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0660114B2 (en) | 1994-08-10 |
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