3-amino-3-(4-methoxyphenyl)propanenitrile | 1270390-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-amino-3-(4-methoxyphenyl)propanenitrile
• CAS: 1270390-44-7
• 化学式: C₁₀H₁₂N₂O
• mdl: MFCD18701994
• 分子量: 176.218
• InChiKey: XUXIWRVFCJZXKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-3-(4-methoxyphenyl)propanenitrile 在 水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (3R)-3-amino-3-(4-methoxyphenyl)propanenitrile 、 (3S)-3-amino-3-(4-methoxyphenyl)propanenitrile 、 (3R)-3-amino-3-(4-methoxyphenyl)propanamide 、 (3S)-3-amino-3-(4-methoxyphenyl)propanamide
  参考文献：
  名称：

  Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870

  摘要：

  A range of beta-aminonitriles (3-amino-3-phenylpropanenitrile and derivatives) were synthesised by reaction of various benzonitriles with acetonitrile and subsequent reduction of the resulting acrylonitrile products. These compounds were hydrolysed to the corresponding amides using the nitrile biocatalytic activity of Rhodococccus rhodochrous ATCC BAA-870. Results showed that the nitrile hydratase enzyme was enantioselective for these compounds, in particular 3-amino-3-p-tolylpropanenitrile and 3-amino-3-(4-methoxyphenyl)propanenitrile and the corresponding amides (up to 85% in one case). The reactions were performed at pH 9.0 after initial attempts at pH 7.0 were unsuccessful, most likely as a result of protonation of the 3-amino group at the lower pH. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.12.005
• 作为产物：
  描述：

  3-amino-3-(4-methoxyphenyl)acrylonitrile 在 盐酸 、 sodium cyanoborohydride 、 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以53%的产率得到3-amino-3-(4-methoxyphenyl)propanenitrile
  参考文献：
  名称：

  Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870

  摘要：

  A range of beta-aminonitriles (3-amino-3-phenylpropanenitrile and derivatives) were synthesised by reaction of various benzonitriles with acetonitrile and subsequent reduction of the resulting acrylonitrile products. These compounds were hydrolysed to the corresponding amides using the nitrile biocatalytic activity of Rhodococccus rhodochrous ATCC BAA-870. Results showed that the nitrile hydratase enzyme was enantioselective for these compounds, in particular 3-amino-3-p-tolylpropanenitrile and 3-amino-3-(4-methoxyphenyl)propanenitrile and the corresponding amides (up to 85% in one case). The reactions were performed at pH 9.0 after initial attempts at pH 7.0 were unsuccessful, most likely as a result of protonation of the 3-amino group at the lower pH. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.12.005

文献信息

• 10.1021/acs.orglett.4c01673
  作者：Liu, Wei、Hou, Hao、Jing, Haochuan、Huang, Shiqing、Ou, Wei、Su, Chenliang

  DOI：10.1021/acs.orglett.4c01673

  日期：——

  β-Amino nitriles are important molecular scaffolds. Cyanoalkylation of imines is the most straightforward method for the construction of these scaffolds. In this study, we report the novel cyanoalkylation of imines via radical coupling enabled by a photoactive electron donor–acceptor complex. This strategy is characterized by mild conditions, broad reaction scopes, and high atom economy. The scalability

  β-氨基腈是重要的分子支架。亚胺的氰烷基化是构建这些支架的最直接的方法。在这项研究中，我们报道了通过光敏电子供体-受体复合物实现的自由基偶联实现亚胺的新型氰烷基化。该策略具有条件温和、反应范围广、原子经济性高等特点。该策略的可扩展性和实用性通过 40 g 连续流动系统得到了证明，从中获得了多种重要的药物相关分子。
• Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870
  作者：Varsha Chhiba、Moira L. Bode、Kgama Mathiba、Wendy Kwezi、Dean Brady

  DOI：10.1016/j.molcatb.2011.12.005

  日期：2012.4

  A range of beta-aminonitriles (3-amino-3-phenylpropanenitrile and derivatives) were synthesised by reaction of various benzonitriles with acetonitrile and subsequent reduction of the resulting acrylonitrile products. These compounds were hydrolysed to the corresponding amides using the nitrile biocatalytic activity of Rhodococccus rhodochrous ATCC BAA-870. Results showed that the nitrile hydratase enzyme was enantioselective for these compounds, in particular 3-amino-3-p-tolylpropanenitrile and 3-amino-3-(4-methoxyphenyl)propanenitrile and the corresponding amides (up to 85% in one case). The reactions were performed at pH 9.0 after initial attempts at pH 7.0 were unsuccessful, most likely as a result of protonation of the 3-amino group at the lower pH. (C) 2012 Elsevier B.V. All rights reserved.