[benzyl[(1S,2R)-2-chloro-1-methyl-2-phenylethyl]amino]acetonitrile | 613688-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [benzyl[(1S,2R)-2-chloro-1-methyl-2-phenylethyl]amino]acetonitrile
• 英文别名: 2-[benzyl-[(1R,2S)-1-chloro-1-phenylpropan-2-yl]amino]acetonitrile
• CAS: 613688-63-4
• 化学式: C₁₈H₁₉ClN₂
• 分子量: 298.815
• InChiKey: HTZBMYIYJCRVSY-YJBOKZPZSA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  414.2±40.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [benzyl[(1S,2R)-2-chloro-1-methyl-2-phenylethyl]amino]acetonitrile 在 2-hydroxybenzotriazol 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 85.0h， 生成 methyl (2S)-2-[[(2R,3S,4S)-1-benzyl-4-methyl-3-phenylazetidine-2-carbonyl]amino]propanoate
  参考文献：
  名称：

  Synthesis of enantiopure azetidine 2-carboxylic acids and their incorporation into peptides

  摘要：

  Enantiopure azetidine 2-carboxylic acids were prepared by hydrolysis of the corresponding 2-cyano azetidines, without ring cleavage of the azetidine or epimerization. The produced amino acids, which are conformationally constrained analogues of phenylalanine. can be cleanly debenzylated and used for the synthesis of tripeptides. In the course of the synthesis of new enantiopure 2-cyano azetidines through intramolecular alkylation of a metallated amino nitrile, it was found that the involved anionic cyclisation can be thermodynamically controlled, thus enhancing its diastereoselectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00493-2
• 作为产物：
  描述：

  NH-benzyl-(1R,2S)-norephedrine 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 13.0h， 生成 [benzyl[(1S,2R)-2-chloro-1-methyl-2-phenylethyl]amino]acetonitrile
  参考文献：
  名称：

  Synthesis of enantiopure azetidine 2-carboxylic acids and their incorporation into peptides

  摘要：

  Enantiopure azetidine 2-carboxylic acids were prepared by hydrolysis of the corresponding 2-cyano azetidines, without ring cleavage of the azetidine or epimerization. The produced amino acids, which are conformationally constrained analogues of phenylalanine. can be cleanly debenzylated and used for the synthesis of tripeptides. In the course of the synthesis of new enantiopure 2-cyano azetidines through intramolecular alkylation of a metallated amino nitrile, it was found that the involved anionic cyclisation can be thermodynamically controlled, thus enhancing its diastereoselectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00493-2

文献信息

• N-Cyanomethyl-β-chloroamines: a convenient source of aziridinium ions
  作者：François Couty、Gwilherm Evano、Damien Prim

  DOI：10.1016/j.tetlet.2005.02.016

  日期：2005.3

  N-Cyanomethyl-β-chloroamines smoothly react with a range of alcohols or amines to give regio- and stereoselectively 1,2-aminoethers or 1,2-diamines. The reaction proceeds through the formation of an intermediate aziridinium ion. The N-cyanomethyl group can then be cleaved easily.

  N-氰甲基-β-氯胺能与多种醇或胺平稳反应，生成区域和立体选择性的1,2-氨基醚或1,2-二胺。反应通过形成中间体叠氮鎓离子而进行。该Ñ氰基可以很容易地切割。
• Alkylation of indoles by aziridinium ions: new rapid access to tetrahydro-β-carbolines (THBCs)
  作者：Laurence Menguy、Cheikh Lo、Jérôme Marrot、François Couty

  DOI：10.1016/j.tet.2014.05.009

  日期：2014.7