Methyl 3-[(cyanomethyl)amino]propanoate | 446822-47-5

• 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: Methyl 3-[(cyanomethyl)amino]propanoate
• 英文别名: methyl 3-(cyanomethylamino)propanoate
• CAS: 446822-47-5
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: LHYHUMYUAVSYTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 3-[(cyanomethyl)amino]propanoate 在 palladium on activated charcoal 锂硼氢 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 (2S,3S)-2-Cyano-3-(2-hydroxy-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  New strategies towards proline derivatives as conformationally constrained arginine analogues

  摘要：

  The cyano derivatives of 3-functionalized dehydroprolines led to arginine semi-constrained analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00424-0
• 作为产物：
  描述：

  3-氨基丙酸甲酯盐酸盐 、 氯乙腈 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以92%的产率得到Methyl 3-[(cyanomethyl)amino]propanoate
  参考文献：
  名称：

  Aminomethylation of lithiated nicotinamide: access to new pyridolactams

  摘要：

  New 2,3-dihydropyrrolopyridinones were conveniently prepared by trapping lithiated pyridine carboxamides, with highly reactive formimines. In this Letter, we report that a wide range of N-functionalised compounds can be synthesised in one step by this process, allowing the presence of ethers, acetals or ester moieties. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.109

文献信息

• Aminomethylation of lithiated nicotinamide: access to new pyridolactams
  作者：Emilie Prieur、Rabah Azzouz、Geoffrey Deguest、Corinne Fruit、Laurent Bischoff、Francis Marsais

  DOI：10.1016/j.tetlet.2007.11.109

  日期：2008.1

  New 2,3-dihydropyrrolopyridinones were conveniently prepared by trapping lithiated pyridine carboxamides, with highly reactive formimines. In this Letter, we report that a wide range of N-functionalised compounds can be synthesised in one step by this process, allowing the presence of ethers, acetals or ester moieties. (C) 2007 Elsevier Ltd. All rights reserved.
• New strategies towards proline derivatives as conformationally constrained arginine analogues
  作者：Nadia Pellegrini、Martine Schmitt、Sébastien Guery、Jean-Jacques Bourguignon

  DOI：10.1016/s0040-4039(02)00424-0

  日期：2002.4

  The cyano derivatives of 3-functionalized dehydroprolines led to arginine semi-constrained analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.