(2S)-1-(2-azidobenzoyl)-N-methoxy-N-methylpyrrolidine-2-carboxamide | 1016557-03-1

• 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)-1-(2-azidobenzoyl)-N-methoxy-N-methylpyrrolidine-2-carboxamide
• CAS: 1016557-03-1
• 化学式: C₁₄H₁₇N₅O₃
• 分子量: 303.321
• InChiKey: VRPGALLHLOKEBV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-1-(2-azidobenzoyl)-N-methoxy-N-methylpyrrolidine-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以65%的产率得到(11aS)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-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：

  二甲羟胺盐酸盐 、 (2S)-N-(2-azidobenzoyl)pyrrolidine-2-carboxylic acid 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)-1-(2-azidobenzoyl)-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

文献信息

• A One-Pot Azido Reductive Tandem Mono-N-Alkylation Employing Dialkylboron Triflates: Online ESI-MS Mechanistic Investigation
  作者：Nagula Shankaraiah、Nagula Markandeya、Vunnam Srinivasulu、Kokkonda Sreekanth、Ch. Sanjeeva Reddy、Leonardo S. Santos、Ahmed Kamal

  DOI：10.1021/jo200931m

  日期：2011.9.2

  mono-N-alkylation of both aromatic and aliphatic azides using dialkylboron triflates as alkylating agents has been examined under standardized reaction conditions. This methodology after optimization has been employed toward the syntheses of various secondary alkyl as well as aryl amines, including the synthesis of N10-butylated pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones via in situ azido reductive-cyclization

  在标准反应条件下，已经研究了使用二烷基硼三氟甲磺酸酯作为烷基化剂的芳香族和脂肪族叠氮化物的有效一锅还原串联单-N-烷基化反应。优化后的该方法已用于合成各种仲烷基以及芳基胺，包括合成N10丁基化吡咯并[2,1- c通过原位叠氮基还原环化过程得到] [1,4]苯并二氮杂-5,11-二酮。该协议特别吸引人，它提供了一种环境友好且实用的方法，可用于从有机叠氮化物进行单N-烷基化而无需使用有毒催化剂或腐蚀性烷基化剂。另外，已经研究了机理方面，并且通过ESI-MS / MS在线监测反应来拦截和表征了与该选择性转化有关的中间体。
• A facile intramolecular azido/amido reductive cyclization approach: synthesis of pyrrolobenzodiazepines and their dimers
  作者：Ahmed Kamal、N. Shankaraiah、N. Markandeya、K. Laxma Reddy、Ch. Sanjeeva Reddy

  DOI：10.1016/j.tetlet.2008.01.004

  日期：2008.2

  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.