2,3-dihydro-2-methyl-2,4-dipropyl-1H-1,5-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: 2,3-dihydro-2-methyl-2,4-dipropyl-1H-1,5-benzodiazepine
• 英文别名: 2-methyl-2,4-dipropyl-2,3-dihydro-1H-1,5-benzodiazepine；2-methyl-2,4-dipropyl-2,3-dihydro-1H-benzo[b][1,4]diazepine；2-Methyl-2,4-dipropyl-2,3-dihydro-1H-benzo[b][1,4]diazepin；2-Methyl-2,4-dipropyl-1,3-dihydro-1,5-benzodiazepine
• 化学式: C₁₆H₂₄N₂
• 分子量: 244.38
• InChiKey: UOGZETKWCGLKDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2-methyl-2,4-dipropyl-1H-1,5-benzodiazepine 生成 丙烷 、 异己烯 、 alkaline earth salt of/the/ methylsulfuric acid 、 methane
  参考文献：
  名称：

  The Reaction of o-Phenylenediamines with Carbonyl Compounds. II. Aliphatic Ketones¹

  摘要：

  DOI：

  10.1021/ja01147a026
• 作为产物：
  描述：

  2-戊酮 、 邻苯二胺 在 silica gel-supported sulfuric acid 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以90%的产率得到2,3-dihydro-2-methyl-2,4-dipropyl-1H-1,5-benzodiazepine
  参考文献：
  名称：

  硅胶负载的硫酸催化合成1,5-苯并二氮杂卓衍生物

  摘要：

  二氧化硅凝胶支持硫酸已被发现是用于1,5-苯并二氮杂将来自合成的有效的催化剂在乙腈溶剂中的邻苯二胺和酮。该方法简单，有效，环境友好，收率更高。与经典反应条件相比，这种新方法始终具有在室温下具有出色的收率（80–97％）和较短的反应时间（30–150分钟）的优势。J.杂环化​​学，（2009）。

  DOI：

  10.1002/jhet.174

文献信息

• Silica gel-supported sulfuric acid catalyzed synthesis of 1,5-benzodiazepine derivatives
  作者：D. Shobha、M. Adharvana Chari、K. Mukkanti、K. H. Ahn

  DOI：10.1002/jhet.174

  日期：2009.9

  Silica gel-supported sulfuric acid has been found to be an efficient catalyst for the synthesis of 1,5-benzodiazepines from o-phenylenediamine and ketones in acetonitrile solvent. This method is simple, effective, and environmentally friendly and gives better yields. Compared to the classical reaction conditions, this new method consistently has the advantage of excellent yields (80–97%) and short

  二氧化硅凝胶支持硫酸已被发现是用于1,5-苯并二氮杂将来自合成的有效的催化剂在乙腈溶剂中的邻苯二胺和酮。该方法简单，有效，环境友好，收率更高。与经典反应条件相比，这种新方法始终具有在室温下具有出色的收率（80–97％）和较短的反应时间（30–150分钟）的优势。J.杂环化​​学，（2009）。
• Catalyst-free synthesis of benzodiazepines and benzimidazoles using glycerol as recyclable solvent
  作者：Catia S. Radatz、Rodrigo B. Silva、Gelson Perin、Eder J. Lenardão、Raquel G. Jacob、Diego Alves

  DOI：10.1016/j.tetlet.2011.05.142

  日期：2011.8

  We described herein the use of glycerol as solvent in the catalyst-free synthesis of benzodiazepines and benzimidazoles. This simple and efficient method furnishes the corresponding 1-H-1,5-benzodiazepines and 1,2-disubstituted benzimidazoles in good yields by the condensation of o-phenylenediamine with several ketones and aldehydes, respectively. In addition, glycerol can be easily re-utilized for

  我们在本文中描述了在无催化剂的苯并二氮杂卓和苯并咪唑的合成中甘油作为溶剂的用途。这种简单而有效的方法通过邻苯二胺分别与几种酮和醛缩合，以高收率提供了相应的1 - H -1,5-苯并二氮杂卓和1,2-二取代的苯并咪唑。另外，甘油可以容易地重新用于进一步的缩合反应多达四次而不会失去活性。
• Simultaneous reduction of the nitro group and the azide group in o -nitrophenylazide induced by the TiCl 4 /Sm system: a novel synthesis of 2,3-dihydro-1 H -1,5-benzodiazepines
  作者：Weihui Zhong、Yongmin Zhang、Xiaoyuan Chen

  DOI：10.1016/s0040-4039(00)01888-8

  日期：2001.1

  o-Nitrophenylazide was treated with the low-valent titanium reagent derived from the TiCl4/Sm system to produce the intermediate 2 in situ, which was a 'living' double-anion and reacted readily with ketones containing active methyl or methylene groups to afford 2,3-dihydro-1H-1,5-benzodiazepines in moderate to high yields under mild and neutral conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Zhong; Zhang; Chen, Journal of Chemical Research - Part S, 2000, # 11, p. 532 - 534
  作者：Zhong、Zhang、Chen

  DOI：——

  日期：——
• Ultrasound enhanced synthesis of 1,5-benzodiazepinic heterocyclic rings
  作者：Karla P. Guzen、Rodrigo Cella、Hélio A. Stefani

  DOI：10.1016/j.tetlet.2006.09.043

  日期：2006.11

  1,5-Benzodiazepines are synthesized by a reaction of o-phenylenediamines with a diketone or ketones series by ultrasound irradiation in presence of APTS. The condensation occurred in a mild condition with good to excellent yields. (c) 2006 Elsevier Ltd. All rights reserved.