3-acetoxy-butyronitrile | 54529-88-3

• 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: 3-acetoxy-butyronitrile
• 英文别名: 3-Acetoxy-butyronitril；β-Acetoxy-buttersaeure-nitril；β-Acetoxy-butyronitril；2-Cyano-1-methylethyl acetate；1-cyanopropan-2-yl acetate
• CAS: 54529-88-3
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: AJKBXPHAHZIXMA-UHFFFAOYSA-N

物化性质

• 沸点：
  210.0±23.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  3-acetoxy-butyronitrile 以35%的产率得到
  参考文献：
  名称：

  ITOH, TOSHIYUKI;TAKAGI, YUMIKO;NISHIYAMA, SHIGENORI, J. ORG. CHEM., 56,(1991) N, C. 1521-1524

  摘要：

  DOI：
• 作为产物：
  描述：

  乙烯酮 、 4-(乙酰氧基)-丁腈 生成 3-acetoxy-butyronitrile
  参考文献：
  名称：

  US2383137

  摘要：

  公开号：

文献信息

• 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。
• 3-Hydroxycarboxylic acid production and use in branched polymers
  申请人：——

  公开号：US20020039770A1

  公开（公告）日：2002-04-04

  This invention relates to a process for the preparation of a 3-hydroxycarboxylic acid from a 3-hydroxynitrile. More specifically, 3-hydroxyvaleronitrile is converted to 3-hydroxyvaleric acid in high yield at up to 100% conversion, using as an enzyme catalyst 1) nitrile hydratase activity and amidase activity or 2) nitrilase activity of a microbial cell. 3-Hydroxyvaleric acid is used as a substitute for &egr;-caprolactone in the preparation of highly branched copolyester.

  本发明涉及一种由 3-羟基腈制备 3-羟基羧酸的工艺。 更具体地说，3-羟基戊腈转化为 3-羟基戊酸的产率很高，转化率可达 100%，使用的酶催化剂为 1) 腈水解酶活性和酰胺酶活性或 2) 微生物细胞的腈酶活性。 在制备高支化共聚聚酯时，3-羟基戊酸可用作&egr;-己内酯的替代品。
• 3-hydroxycarboxylic acid production and use in branched polymers
  申请人：——

  公开号：US20030170837A1

  公开（公告）日：2003-09-11

  This invention relates to a process for the preparation of a 3-hydroxycarboxylic acid from a 3-hydroxynitrile. More specifically, 3-hydroxyvaleronitrile is converted to 3-hydroxyvaleric acid in high yield at up to 100% conversion, using as an enzyme catalyst 1) nitrile hydratase activity and amidase activity or 2) nitrilase activity of a microbial cell. 3-Hydroxyvaleric acid is used as a substitute for &egr;-caprolactone in the preparation of highly branched copolyester.

  本发明涉及一种由 3-羟基腈制备 3-羟基羧酸的工艺。更具体地说，3-羟基戊腈转化为 3-羟基戊酸的产率很高，转化率可达 100%，使用的酶催化剂为 1) 腈水解酶活性和酰胺酶活性或 2) 微生物细胞的腈酶活性。在制备高支化共聚聚酯时，3-羟基戊酸可用作&egr;-己内酯的替代品。
• Enhanced enantioselectivity of an enzymatic reaction by the sulfur functional group. A simple preparation of optically active .beta.-hydroxy nitriles using a lipase
  作者：Toshiyuki Itoh、Yumiko Takagi、Shigenori Nishiyama

  DOI：10.1021/jo00004a033

  日期：1991.2

  The enantioselectivity of a lipase-catalyzed hydrolysis was improved by varying the acyl residue into the sulfur functional one, i.e. the beta-(phenylthio)- or beta-(methylthio)acetoxy group, from acetate or valerate to realize satisfactory resolution of beta-hydroxy nitriles using lipase P (Pseudomonas sp.).
• 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.