(S)-acetoxybutyronitrile | 134527-00-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-acetoxybutyronitrile
• 英文别名: [(2S)-1-cyanopropan-2-yl] acetate
• CAS: 134527-00-7
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: AJKBXPHAHZIXMA-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-(+)-3-羟基丁腈 、 乙酰氯 在 吡啶 作用下， 生成 (S)-acetoxybutyronitrile
  参考文献：
  名称：

  Enhanced Enantioselectivity of the Lipase-Catalyzed Hydrolysis by the Addition of a Catalytic Amount of an Amino Alcohol

  摘要：

  研究发现，L-甲硫醇（L-MetOH）是一种能有效提高脂肪酶催化解水反应对映选择性的添加剂。实验发现，L-MetOH促进了(R)-3-乙酰氧基丁腈（1）的酶催化解水反应，而抑制了(S)-1的反应。

  DOI：

  10.1246/bcsj.64.624

文献信息

• Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis
  作者：Toshiyuki Itoh、Koichi Mitsukura、Wipa Kanphai、Yumiko Takagi、Hiroshi Kihara、Hiroshi Tsukube

  DOI：10.1021/jo971288m

  日期：1997.12.1

  Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the-reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomethyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.
• Enhanced reaction rate and enantioselectivity in lipase-catalyzed hydrolysis by addition of a crown ether
  作者：Toshiyuki Itoh、Yuji Hiyama、Akio Betchaku、Hiroshi Tsukube

  DOI：10.1016/s0040-4039(00)77639-8

  日期：1993.4

  Both reaction rate and enantioselectivity in a lipase-catalyzed hydrolysis of beta-acetoxybutyronitrile were significantly enhanced by addition of hydroxymethyl-12-crown-4.
• Crown Ethers as Regulators of Enzymatic Reactions:  Enhanced Reaction Rate and Enantioselectivity in Lipase-Catalyzed Hydrolysis of 2-Cyano-1-methylethyl Acetate
  作者：Toshiyuki Itoh、Yumiko Takagi、Takako Murakami、Yuji Hiyama、Hiroshi Tsukube

  DOI：10.1021/jo951598+

  日期：1996.1.1

  Both reaction rate and enantioselectivity in lipase-catalyzed hydrolysis of 2-cyano-1-methylethyl acetate were significantly changed by addition of some crown ethers. Although various crown ethers accelerated the reaction rate, the enantioselectivity greatly depended on the nature of each one. Among 27 crown ethers and 5 polyethers tested, benzo-crown, armed azacrown, and thiacrown ethers offered high enantioselectivity of the lipase-catalyzed hydrolysis. Hydrophobicity and chirality of the crown ether did not affect the hydrolysis behavior, but its concentration greatly influenced enantioselectivity. Two hundred fifty or more times the crown ether, molarity based on the enzyme, was required to attain satisfactorily high reaction rate and enantioselectivity.
• Enhanced Enantioselectivity of the Lipase-Catalyzed Hydrolysis by the Addition of a Catalytic Amount of an Amino Alcohol
  作者：Toshiyuki Itoh、Eri Ohira、Yumiko Takagi、Shigenori Nishiyama、Kaoru Nakamura

  DOI：10.1246/bcsj.64.624

  日期：1991.2

  l-Methioninol (l-MetOH) was discovered to be an effective additive for improving the enantioselectivity of lipase-catalyzed hydrolysis. It was found that l-MetOH accelerated the enzyme-catalyzed hydrolysis of (R)-3-acetoxybutyronitrile (1) and inhibited that of (S)-1.

  研究发现，L-甲硫醇（L-MetOH）是一种能有效提高脂肪酶催化解水反应对映选择性的添加剂。实验发现，L-MetOH促进了(R)-3-乙酰氧基丁腈（1）的酶催化解水反应，而抑制了(S)-1的反应。