(2S,4R)-1-(2-azido-5-methoxy-4-phenylmethoxybenzoyl)-4-hydroxy-N-methoxy-N-methylpyrrolidine-2-carboxamide | 1016557-25-7

• 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: (2S,4R)-1-(2-azido-5-methoxy-4-phenylmethoxybenzoyl)-4-hydroxy-N-methoxy-N-methylpyrrolidine-2-carboxamide
• CAS: 1016557-25-7
• 化学式: C₂₂H₂₅N₅O₆
• 分子量: 455.47
• InChiKey: BXTZUBMWVBCTML-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1-(2-azido-5-methoxy-4-phenylmethoxybenzoyl)-4-hydroxy-N-methoxy-N-methylpyrrolidine-2-carboxamide 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 以68%的产率得到(6aS,8R)-8-hydroxy-2-methoxy-3-phenylmethoxy-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
  参考文献：
  名称：

  A facile intramolecular azido/amido reductive cyclization approach: synthesis of pyrrolobenzodiazepines and their dimers

  摘要：

  A new synthetic pathway has been developed for the preparation of imine-containing pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) and their dimers. Selective reduction of aromatic azides as well as aliphatic amides in a single step leading to an intramolecular reductive cyclization process by employing LiAlH(4) or LiBH(4) provides the cyclized imines. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.004
• 作为产物：
  描述：

  C₂₀H₂₀N₄O₆ 、 二甲羟胺盐酸盐 在 N-甲基吗啉 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,4R)-1-(2-azido-5-methoxy-4-phenylmethoxybenzoyl)-4-hydroxy-N-methoxy-N-methylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  A facile intramolecular azido/amido reductive cyclization approach: synthesis of pyrrolobenzodiazepines and their dimers

  摘要：

  A new synthetic pathway has been developed for the preparation of imine-containing pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) and their dimers. Selective reduction of aromatic azides as well as aliphatic amides in a single step leading to an intramolecular reductive cyclization process by employing LiAlH(4) or LiBH(4) provides the cyclized imines. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.004