[benzyl[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]amino]acetonitrile | 613688-62-3

• 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-hydroxy-1-methyl-2-phenylethyl]amino]acetonitrile
• 英文别名: 2-[benzyl-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]amino]acetonitrile
• CAS: 613688-62-3
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: KXLLGEKCJDGYBG-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [benzyl[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]amino]acetonitrile 在 2-hydroxybenzotriazol 、 三甲基氯硅烷 、 氯化亚砜 、 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 、 甲醇 、 二氯甲烷 为溶剂， 反应 110.08h， 生成 (S)-2-[((2R,3S,4S)-4-Methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester
  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 、 溴乙腈 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以97%的产率得到[benzyl[(1S,2R)-2-hydroxy-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