新規光学活性カルボン酸の調製とらせん誘起剤への利用 Preparation of Novel Optically Active Carboxylic Acids and Application as Chiral Dopants for Nematic Liquid Crystals

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Chiral 2-phenylpropanoic acid derivatives and 2-methylchroman-2-carboxylic acid derivatives were prepared as new chiral dopants for nematic liquid crystals. The optically active (<I>S</I>) -2- (4-butylphenyl) propanoic acid was prepared from (<I>S</I>) -2-propanoic acid chloride and butylbenzene using an analogous method employed for the synthesis of ibuprofen. Their helical twisting power (HTP) was determined and the relationship with their functional groups and flexible terminal structures was studied. (<I>S</I>) -1- [4- (<I>trans</I>-4-Butylcyclohexyl) phenyl] -2-phenylpropane-1-one showed a large HTP value 20.4 μm<SUP>-1</SUP> (MHTP = 5.50 μ<SUP>-1</SUP>mol<SUP>-1</SUP>kg).<BR>The HTP was also studied for 2-methylchroman-2-carboxylic acid derivatives having a chiral center in the cyclic structure. The starting material, 6-benzyloxy-2-methylchroman-2-carboxylic acid, was prepared and resolved by a diastereomeric salt formation method. Its ethyl ester showed a good HTP value 11.2 μm<SUP>-1</SUP> (MHTP = 3.65 μm<SUP>-1</SUP> mol<SUP>-1</SUP> kg) showing the rigid cyclic structure having a benzyl group at the 6-position was also effective for chiral induction.

収録刊行物

  • 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN

    有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 64(10), 1032-1040, 2006-10-01

    The Society of Synthetic Organic Chemistry, Japan

参考文献:  28件中 1-28件 を表示

  • <no title>

    野平博之編著

    光学活性体その有機工業化学, 1989

    被引用文献1件

  • Synthesis and Application of Chiral Liquid Crystals

    PAULUTH D.

    Chirality in Industry II, 263, 1997

    被引用文献1件

  • <no title>

    KUBALL H.-G.

    Mol. Cryst. Liq. Cryst. 261, 205, 1995

    被引用文献1件

  • <no title>

    GOODBY J. W.

    J. Mater. Chem. 1, 307, 1991

    被引用文献1件

  • <no title>

    KUBALL H.-G.

    Mol. Cryst. Liq. Cryst. 261, 205, 1995

    被引用文献1件

  • <no title>

    STUTZER C.

    Liq. Cryst. 21, 557, 1996

    被引用文献1件

  • <no title>

    AOKI Y.

    Bull. Chem. Soc. Jpn. 74, 2219, 2001

    被引用文献1件

  • <no title>

    KUSUMOTO T.

    Ferroelectrics 148, 153, 1993

    被引用文献1件

  • <no title>

    TAKEHARA S.

    Ferroelectrics 148, 195, 1993

    被引用文献1件

  • <no title>

    SHITARA H.

    Chem. Lett., 1998

    被引用文献1件

  • <no title>

    SHITARA H.

    Bull. Chem. Soc. Jpn. 73, 259, 2000

    被引用文献1件

  • <no title>

    岡野光治編

    液晶, 1991

    被引用文献1件

  • <no title>

    吉野勝美

    液晶とディスプレ応用の基礎, 1994

    被引用文献1件

  • <no title>

    高西陽一

    液晶 5(2), 122, 2001

    被引用文献1件

  • <no title>

    松村清利

    応用物理, 1974

    被引用文献1件

  • <no title>

    液晶若手研究会編

    液晶材料研究の基礎と新展開, 1998

    被引用文献1件

  • <no title>

    VERTOGEN G.

    Thermotropic Liquid Crystals, Fundamentals, 1988

    被引用文献1件

  • <no title>

    NYSTROM R. F.

    J. Am. Chem. Soc. 80, 2896, 1958

    被引用文献1件

  • <no title>

    WEST C. T.

    J. Org. Chem. 38, 2675, 1972

    被引用文献1件

  • <no title>

    CANO R.

    Bull. Soc. Franc. Mineralog. Crystallogr. 91, 20, 1968

    被引用文献1件

  • <no title>

    西村

    特開平7-97380, 1995

    被引用文献1件

  • <no title>

    NISHIKAWA J.

    Nippon Kagaku Kaishi, 1979

    被引用文献1件

  • <no title>

    BURGESS E. M.

    J. Org. Chem. 38, 26, 1973

    被引用文献1件

  • <no title>

    GOODBY J. W.

    Mol. Cryst. Liq. Cryst. 292, 245, 1997

    被引用文献2件

  • <no title>

    AOKI Y.

    Mol. Cryst. Liq. Cryst. 346, 35, 2000

    被引用文献7件

  • <no title>

    AOKI Y.

    Mol. Cryst. Liq. Cryst. 346, 35, 2000

    被引用文献7件

  • <no title>

    PICCOLO O.

    J. Org. Chem. 52, 10, 1987

    被引用文献2件

  • <no title>

    CLAREMON D. A.

    Tetrahedron Lett. 29, 2155, 1988

    被引用文献1件

各種コード

  • NII論文ID(NAID)
    10018311570
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    ART
  • ISSN
    00379980
  • NDL 記事登録ID
    8536439
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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