4-cyanobutanoic acid ammonium salt

• 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: 4-cyanobutanoic acid ammonium salt
• 英文别名: Azane;4-cyanobutanoic acid；azane;4-cyanobutanoic acid
• 化学式: C₅H₇NO₂*H₃N
• 分子量: 130.147
• InChiKey: PDGOWVXNRNSXNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-cyanobutanoic acid ammonium salt 在 镍 ammonium hydroxide 、 氢气 作用下， 以 水 为溶剂， 70.0 ℃ 、3.45 MPa 条件下， 反应 3.5h， 以74%的产率得到哌啶酮
  参考文献：
  名称：

  Chemoenzymic Production of Lactams from Aliphatic α,ω-Dinitriles

  摘要：

  Five- and six-membered ring lactams have been prepared by first converting an aliphatic alpha,omega-dinitrile to an omega-cyanocarboxylic acid ammonium salt, using a microbial cell catalyst having an aliphatic nitrilase activity (Acidovorax: facilis 72W, ATCC 55746) or a combination of nitrile hydratase and amidase activities (Comamonas testosteroni 5-MGAM-4D, ATCC 55744). The omega-cyanocarboxylic acid ammonium salt was then directly converted to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate omega-cyanocarboxylic acid or omega-aminocarboxylic acid. Only one of two possible lactam products was produced from alpha-alkyl-substituted alpha,omega-dinitriles, where the nitrilase of A. facilis 72W regioselectively hydrolyzed only the omega-cyano group to produce a single cyanocarboxylic acid ammonium salt in greater than 98% yield.

  DOI：

  10.1021/jo9804386
• 作为产物：
  描述：

  戊二腈 反应 4.0h， 以7.7%的产率得到戊二酸铵
  参考文献：
  名称：

  Chemoenzymic Production of Lactams from Aliphatic α,ω-Dinitriles

  摘要：

  Five- and six-membered ring lactams have been prepared by first converting an aliphatic alpha,omega-dinitrile to an omega-cyanocarboxylic acid ammonium salt, using a microbial cell catalyst having an aliphatic nitrilase activity (Acidovorax: facilis 72W, ATCC 55746) or a combination of nitrile hydratase and amidase activities (Comamonas testosteroni 5-MGAM-4D, ATCC 55744). The omega-cyanocarboxylic acid ammonium salt was then directly converted to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate omega-cyanocarboxylic acid or omega-aminocarboxylic acid. Only one of two possible lactam products was produced from alpha-alkyl-substituted alpha,omega-dinitriles, where the nitrilase of A. facilis 72W regioselectively hydrolyzed only the omega-cyano group to produce a single cyanocarboxylic acid ammonium salt in greater than 98% yield.

  DOI：

  10.1021/jo9804386