(+/-)-3-O-(acetyl)-4-cyanobutanoic acid | 151061-75-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-3-O-(acetyl)-4-cyanobutanoic acid
• 英文别名: 3-Acetyloxy-4-cyanobutanoic acid
• CAS: 151061-75-5
• 化学式: C₇H₉NO₄
• 分子量: 171.153
• InChiKey: DAQILPSHPRRCQP-UHFFFAOYSA-N

物化性质

• 沸点：
  382.9±37.0 °C(predicted)
• 密度：
  1.258±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (+/-)-3-O-(acetyl)-4-cyanobutanoic acid 以100%的产率得到(+/-)-methyl-(3-O--4-cyano)-butanoate
  参考文献：
  名称：

  Stereoselective hydrolysis of nitriles and amides under mild conditions using a whole cell catalyst

  摘要：

  An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid. A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84%. Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.

  DOI：

  10.1016/s0957-4166(00)80215-3
• 作为产物：
  描述：

  β-Acetoxyglutaronitrile 反应 65.0h， 以45%的产率得到(+/-)-3-O-(acetyl)-4-cyanobutanoic acid
  参考文献：
  名称：

  Stereoselective hydrolysis of nitriles and amides under mild conditions using a whole cell catalyst

  摘要：

  An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid. A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84%. Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.

  DOI：

  10.1016/s0957-4166(00)80215-3

文献信息

• Crosby John A., Parratt Julian S., Turner Nicholas J., Tetrahedron, 3 (1992) N 12, S 1547-1550
  作者：Crosby John A., Parratt Julian S., Turner Nicholas J.

  DOI：——

  日期：——

表征谱图