1-(Cyanomethyl)propyl acetate | 154524-64-8

• 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: 1-(Cyanomethyl)propyl acetate
• 英文别名: 1-cyanobutan-2-yl acetate
• CAS: 154524-64-8
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: JCVZTBWPZRMHQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(Cyanomethyl)propyl acetate 在 1,4,8,11-四硫杂环十四烷 、 Lipase PS 作用下， 以 吡啶 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.0h， 生成 (R)-1-(cyanomethyl)propyl acetate
  参考文献：
  名称：

  Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

  摘要：

  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.

  DOI：

  10.1021/jo971288m
• 作为产物：
  描述：

  3-羟基戊腈 、 乙酰氯 以 吡啶 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(Cyanomethyl)propyl acetate
  参考文献：
  名称：

  Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

  摘要：

  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.

  DOI：

  10.1021/jo971288m

文献信息

• INHIBITORS OF SERINE PROTEASES
  申请人：Cottrell Kevin M.

  公开号：US20110182856A1

  公开（公告）日：2011-07-28

  The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt thereof. These compounds inhibit serine protease, particularly the hepatitis C virus NS3-NS4A protease.

  本发明涉及式(I)化合物或其药学上可接受的盐。这些化合物抑制丝氨酸蛋白酶，特别是丙型肝炎病毒NS3-NS4A蛋白酶。
• NOVEL ACETOACETYL-CoA REDUCTASE AND PROCESS FOR PRODUCING OPTICALLY ACTIVE ALCOHOL
  申请人：KANEKA CORPORATION

  公开号：EP1688480A2

  公开（公告）日：2006-08-09

  An object of the present invention is to provide a simple and easy process for producing optically active alcohols, specifically, a (R)-3-hydroxypentanenitrile, optically active 3-hydroxybutanoic esters, and optically active 1-phenylethanol derivatives, and to provide a novel enzyme useful for producing the above optically active alcohols, particularly a (R)-3-hydroxypentanenitrile. The present invention provides a novel acetoacetyl-CoA reductase capable of asymmetrically reducing a 3-ketopentanenitrile to produce a (R)-3-hydroxypentanenitrile having an optical purity of 99%e.e. or more; and a process for allowing the novel enzyme or a known acetoacetyl-CoA reductase to act on each of the 3-ketopentanenitrile, an acetoacetic ester, and a 1-phenylethanone derivative to produce a corresponding optically active alcohol.

  本发明的目的是提供一种生产光学活性醇，特别是(R)-3-羟基戊腈、光学活性3-羟基丁酸酯和光学活性1-苯乙醇衍生物的简单易行的工艺，并提供一种用于生产上述光学活性醇，特别是(R)-3-羟基戊腈的新型酶。 本发明提供了一种新型乙酰乙酰-CoA还原酶，它能够不对称地还原3-酮戊腈，生成光学纯度为99%e.e.或更高的(R)-3-羟基戊腈；还提供了一种工艺，使该新型酶或已知的乙酰乙酰-CoA还原酶作用于3-酮戊腈、乙酰乙酸酯和1-苯乙酮衍生物中的每一种，生成相应的光学活性醇。
• Novel acetoacetyl-coa reductase and process for producing optically active alcohol
  申请人：Kawano Shigeru

  公开号：US20070037263A1

  公开（公告）日：2007-02-15

  An object of the present invention is to provide a simple and easy process for producing optically active alcohols, specifically, a (R)-3-hydroxypentanenitrile, optically active 3-hydroxybutanoic esters, and optically active 1-phenylethanol derivatives, and to provide a novel enzyme useful for producing the above optically active alcohols, particularly a (R)-3-hydroxypentanenitrile. The present invention provides a novel acetoacetyl-CoA reductase capable of asymmetrically reducing a 3-ketopentanenitrile to produce a (R)-3-hydroxypentanenitrile having an optical purity of 99% e.e. or more; and a process for allowing the novel enzyme or a known acetoacetyl-CoA reductase to act on each of the 3-ketopentanenitrile, an acetoacetic ester, and a 1-phenylethanone derivative to produce a corresponding optically active alcohol.
• US8455497B2
  申请人：——

  公开号：US8455497B2

  公开（公告）日：2013-06-04