5-methyl-4-phenyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine

• 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: 5-methyl-4-phenyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine
• 英文别名: 5-methyl-4-phenyl-5,6-dihydro-4H-benzo[f]pyrrolo[1,2-a][1,4]diazepine；5-Methyl-4-phenyl-4,6-dihydropyrrolo[1,2-a][1,4]benzodiazepine
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: NOMJDCAKQPJFCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丙炔酸甲酯 、 5-methyl-4-phenyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 以56%的产率得到methyl 6-methyl-9-phenyl-6,9-dihydro-5H-pyrrolo[1,2-a][1,6]benzodiazonine-8-carboxylate
  参考文献：
  名称：

  Transformations of 4-arylpyrrolo[1,2-a][1,4]benzodiazepines in three-component reactions with activated alkynes and СН, NH, SH, and ОН acids

  摘要：

  Three-component reactions of tetrahydropyrrolo[1,2-a][1,4] benzodiazepines with methyl propiolate or acetylacetylene and CH, NH, SH, and OH acids were studied in various solvents. The reaction direction is assumed to depend on the nucleophilicity of anion, formed through deprotonation of acid by the anionic center of initial Michael-type zwitterion.

  DOI：

  10.1007/s10593-015-1751-0
• 作为产物：
  描述：

  2-(1-吡咯基)苄胺 在 sodium tetrahydroborate 、 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 水 、 丙酮 、 乙腈 为溶剂， 反应 5.59h， 生成 5-methyl-4-phenyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine
  参考文献：
  名称：

  Synthesis of pyrrolo[1,2-a][1,6]benzodiazonines from pyrrolo[1,2-a][1,4]benzodiazepines and alkynes containing electron-acceptor substituents

  摘要：

  It has been established that the reaction of pyrrolo[1,2-a][1,4]benzodiazepines with activated alkynes gives pyrrolo[1,2-a][1,6]benzodiazonines as the products of diazepine ring expansion. In the case of pyrrolo[1,2-a][1,4]benzodiazepine, substituted with formyl group at the pyrrole ring, both expansion and cleavage of the diazepine fragment can occur.

  DOI：

  10.1007/s10593-013-1340-z

文献信息

• Transformation of 4-Substituted Tetrahydro-Pyrrolobenzodiazepines in a Three-Component Reaction With Methyl Propiolate and Indole
  作者：L. G. Voskressensky、T. N. Borisova、M. I. Babakhanova、A. A. Titov、T. M. Chervyakova、R. A. Novikov、A. V. Butin、V. N. Khrustalev、A. V. Varlamov

  DOI：10.1007/s10593-014-1431-5

  日期：2014.3

  The three-component reaction of 4-phenyl-, p-methoxyphenyl-, and thienylpyrrolo[1,2-a][1,4]benzo-diazepines with methyl propiolate and indole in dichloromethane proceeds through opening of the diazepine ring. The major transformation products isolated are substituted pyrroles, namely, 1-(2-aminomethylphenyl)-5-(arylmethyl)-2-(indol-1(3)-yl)pyrroles and 1-(2-aminomethylphenyl)-2-aryl-(indol-3-yl)-methylpyrroles

  4-二苯基，对甲氧基苯基和噻吩并吡咯并[1,2- a ] [1,4]苯并二氮杂卓与丙酸甲酯和吲哚在二氯甲烷中的三组分反应通过打开二氮杂pine环而进行。分离的主要转化产物是取代的吡咯，即1-（2-氨基甲基苯基）-5-（芳基甲基）-2-（吲哚-1（3）-基）吡咯和1-（2-氨基甲基苯基）-2-芳基-（吲哚-3-基）-甲基吡咯。
• Synthesis of pyrrolo[1,2-a][1,6]benzodiazonines from pyrrolo[1,2-a][1,4]benzodiazepines and alkynes containing electron-acceptor substituents
  作者：L. G. Voskressensky、T. N. Borisova、M. I. Babakhanova、T. M. Chervyakova、A. A. Titov、A. V. Butin、T. A. Nevolina、V. N. Khrustalev、A. V. Varlamov

  DOI：10.1007/s10593-013-1340-z

  日期：2013.10

  It has been established that the reaction of pyrrolo[1,2-a][1,4]benzodiazepines with activated alkynes gives pyrrolo[1,2-a][1,6]benzodiazonines as the products of diazepine ring expansion. In the case of pyrrolo[1,2-a][1,4]benzodiazepine, substituted with formyl group at the pyrrole ring, both expansion and cleavage of the diazepine fragment can occur.
• Transformations of 4-arylpyrrolo[1,2-a][1,4]benzodiazepines in three-component reactions with activated alkynes and СН, NH, SH, and ОН acids
  作者：Leonid G. Voskressensky、Tatiana N. Borisova、Mar’yana I. Babakhanova、Tatiana M. Chervyakova、Alexander A. Titov、Roman A. Novikov、Flavien Toze、Ti Tuyet Anh Dang、Aleksey V. Varlamov

  DOI：10.1007/s10593-015-1751-0

  日期：2015.7

  Three-component reactions of tetrahydropyrrolo[1,2-a][1,4] benzodiazepines with methyl propiolate or acetylacetylene and CH, NH, SH, and OH acids were studied in various solvents. The reaction direction is assumed to depend on the nucleophilicity of anion, formed through deprotonation of acid by the anionic center of initial Michael-type zwitterion.