3-O-(methoxyethoxymethyl)-glutaronitrile | 150966-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(methoxyethoxymethyl)-glutaronitrile
• 英文别名: 3-(2-Methoxyethoxymethoxy)pentanedinitrile
• CAS: 150966-83-9
• 化学式: C₉H₁₄N₂O₃
• 分子量: 198.222
• InChiKey: BKGXOSPCLCRWPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-(methoxyethoxymethyl)-glutaronitrile 在 二甲基溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 45.0h， 生成 methyl (S)-4-cyano-3-hydroxybutanoate
  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：

  3-羟基戊二腈 、 2-甲氧基乙氧基甲基氯 在 sodium hydride 作用下， 生成 3-O-(methoxyethoxymethyl)-glutaronitrile
  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

• Stereoselective hydrolysis of nitriles and amides under mild conditions using a whole cell catalyst
  作者：Timothy Beard、Mark A. Cohen、Julian S. Parratt、Nicholas J. Turner、John Crosby、Jock Moilliet

  DOI：10.1016/s0957-4166(00)80215-3

  日期：1993.6

  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.

表征谱图