2,4-Diisopropyl-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine

• 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: 2,4-Diisopropyl-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine
• 英文别名: 2-Methyl-2,4-di(propan-2-yl)-1,3-dihydro-1,5-benzodiazepine
• 化学式: C₁₆H₂₄N₂
• 分子量: 244.38
• InChiKey: OTNOKPBHTRZGQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 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：

  2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide 、 2,4-Diisopropyl-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine 反应 4.5h， 以72%的产率得到2,4-diisopropyl-2-methyl-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3-dihydro-1,5-benzodiazepine
  参考文献：
  名称：

  Yadav, Ashok K.; Kumar, Manoj; Yadav, Tripti, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 4, p. 461 - 468

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-2-丁酮 、 邻苯二胺 在 potassium aluminum sulfate 作用下， 反应 3.5h， 以87%的产率得到2,4-Diisopropyl-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine
  参考文献：
  名称：

  1,5-苯二氮卓类的明矾催化一锅法无溶剂合成

  摘要：

  明矾 [KAl(SO4)2∙12H2O] 被发现是一种高效、无毒、廉价且对环境无害的催化剂，用于合成 1,5-苯二氮卓类化合物，产率从良好到极好，从 1 摩尔在无溶剂条件下，邻苯二胺与 2 摩尔酮。

  DOI：

  10.1071/ch07316

文献信息

• USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20150376224A1

  公开（公告）日：2015-12-31

  The use of metal-accumulating plants for implementing chemical reactions especially catalytical reactions.

  金属积累植物用于实现化学反应，特别是催化反应的使用。
• Alum-Catalyzed One-Pot Solventless Synthesis of 1,5-Benzodiazepines
  作者：Deepali Mahajan、Tahira Naqvi、Rattan Lal Sharma、Kamal K. Kapoor

  DOI：10.1071/ch07316

  日期：——

  Alum [KAl(SO4)2∙12H2O] was found to be an efficient, non-toxic, cheap, and environmentally benign catalyst for the synthesis of 1,5-benzodiazepines, in good to excellent yields, from the condensation of 1 mole of o-phenylenediamine with 2 moles of ketone under solvent-free conditions.

  明矾 [KAl(SO4)2∙12H2O] 被发现是一种高效、无毒、廉价且对环境无害的催化剂，用于合成 1,5-苯二氮卓类化合物，产率从良好到极好，从 1 摩尔在无溶剂条件下，邻苯二胺与 2 摩尔酮。
• Room temperature ionic liquid promoted synthesis of 1,5-benzodiazepine derivatives under ambient conditions
  作者：D.V Jarikote、S.A Siddiqui、R Rajagopal、Thomas Daniel、R.J Lahoti、K.V Srinivasan

  DOI：10.1016/s0040-4039(03)00096-0

  日期：2003.2

  The reaction of o-phenylenediamines with both acyclic and cyclic ketones in the ionic liquid 1,3-di-n-butylimidazolium bromide afforded 1,5-benzodiazepines in excellent isolated yields in the absence of a catalyst at ambient temperature. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Molecular Iodine Catalyzed Highly Rapid Synthesis of 1,5‐Benzodiazepine Derivatives Under Mild Conditions
  作者：B. P. Bandgar、Sampada V. Bettigeri、Neeta S. Joshi

  DOI：10.1081/scc-120030695

  日期：2004.12.31

  Rapid reaction of o-phenylenediamines with both cyclic and acyclic ketones in the presence of catalytic amount of iodine afforded 1,5-benzodiazepine derivatives in excellent yields at room temperature.
• Anti-neuroinflammatory activity of 1,5-benzodiazepine derivatives
  作者：Sang Keun Ha、Donthabhaktuni Shobha、Eunjung Moon、Murugulla A. Chari、Kagga Mukkanti、Sung-Hoon Kim、Kwang-Hyun Ahn、Sun Yeou Kim

  DOI：10.1016/j.bmcl.2010.04.133

  日期：2010.7

  A series of 2,3-dihydro-1,5-benzodiazepines were synthesized and evaluated for anti-inflammatory effects in microglia cells. Among the 1,5-benzodiazepines tested, compound 3e strongly inhibited LPS-induced nitric oxide ( NO) production, with an IC50 value of 7.0 mu M in the microglia cells. Also, compound 3e significantly inhibited the enzymatic activity of inducible NO synthase ( iNOS) without changes in iNOS protein expression or NO scavenging activity. This result suggests that compound 3e showed anti-neuroinflammatory effects by suppressing iNOS enzyme activity. (C) 2010 Elsevier Ltd. All rights reserved.