(2R,11aS)-2-Hydroxy-8-methyl-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (2R,11aS)-2-Hydroxy-8-methyl-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one
• 英文别名: (6aS,8R)-8-hydroxy-3-methyl-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: OQNRFLWYRIFMAA-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以56%的产率得到(2R,11aS)-2-Hydroxy-8-methyl-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-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

文献信息

• Efficient solid-phase synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepine antitumour antibiotics
  作者：Ahmed Kamal、G.Suresh Kumar Reddy、K.Laxma Reddy、Sadagopan Raghavan

  DOI：10.1016/s0040-4039(02)00188-0

  日期：2002.3

  The solid-phase synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepine (PBD) imines and biologically important pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones on Wang resin using a reduction/cyclization procedure is reported.

  DNA相互作用的吡咯并[2,1- c ] [1,4]苯并二氮杂（PBD）亚胺和生物学上重要的吡咯并[2,1- c ] [1,4]苯并二氮杂5,11-二酮的固相合成据报道，使用还原/环化程序对王树脂进行了分析。
• 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.