8'-methyl-1',2',3',4',10',11a'-hexahydrospiro[cyclohexane-1,11'-dibenzo[b,e][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: 8'-methyl-1',2',3',4',10',11a'-hexahydrospiro[cyclohexane-1,11'-dibenzo[b,e][1,4]diazepine]
• 英文别名: 11-spirocyclocyclohexane-2,3,4,10,11,11a-hexahydro-8-methyl-1H-dibenzo[b,e][1,4]diazepine；11-spirocyclohexane-2,3,4,10,11,11a-hexahydro-8-methyl-1H-dibenzo[b,e][1,4]diazepine；3-Methylspiro[5,6a,7,8,9,10-hexahydrobenzo[b][1,4]benzodiazepine-6,1'-cyclohexane]
• 化学式: C₁₉H₂₆N₂
• 分子量: 282.429
• InChiKey: YDRJUXLPUMAWCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 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 、 8'-methyl-1',2',3',4',10',11a'-hexahydrospiro[cyclohexane-1,11'-dibenzo[b,e][1,4]diazepine] 反应 4.0h， 以90%的产率得到(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(8'-methyl-1',3',4',11a'-tetrahydrospiro[cyclohexane-1,11'-dibenzo[b,e][1,4]diazepin]-10'(2'H)-yl)tetrahydrofuran-3,4-diyl dibenzoate
  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：

  环己酮 、 3,4-二氨基甲苯 在 三氟乙酸 作用下， 反应 12.0h， 以89%的产率得到8'-methyl-1',2',3',4',10',11a'-hexahydrospiro[cyclohexane-1,11'-dibenzo[b,e][1,4]diazepine]
  参考文献：
  名称：

  Investigation of Various Organocatalysts for Improved and Efficient One Pot Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines Under Solvent-Free Condition

  摘要：

  通过邻苯二胺与 a，b-不饱和羰基化合物的一锅三组份缩合反应，合成了一系列 2，3-二氢-1H-1，5-苯并二氮杂卓衍生物，并研究了各种布氏有机酸作为催化剂的效果。在筛选出的各种有机酸中，三氟乙酸是一种多功能催化剂，在无溶剂条件下，相应产物的收率从良好到极佳（84-94 %）。

  DOI：

  10.14233/ajchem.2014.16440

文献信息

• Indium(III) Bromide: A Novel and Efficient Reagent for the Rapid Synthesis of 1,5-Benzodiazepines under Solvent-Free Conditions
  作者：J. S. Yadav、B. V. Reddy、S. Praveenkumar、K. Nagaiah

  DOI：10.1055/s-2004-834939

  日期：——

  o-Phenylenediamines (OPDA) undergo rapid condensation with ketones having hydrogens at the α-position in the presence of 10 mol% indium(III) bromide under extremely mild reaction conditions to afford the corresponding 1,5-benzodiazepines in excellent yields with high selectivity. The remarkable features of this new procedure are high conversions, short reaction times, cleaner reaction profiles, high

  在极其温和的反应条件下，在 10 mol% 溴化铟 (III) 的存在下，邻苯二胺 (OPDA) 与在 α 位具有氢的酮快速缩合，以优异的收率和高选择性得到相应的 1,5-苯二氮卓类化合物. 这种新方法的显着特点是转化率高、反应时间短、反应曲线更清晰、不对称酮的区域选择性高、无溶剂条件以及简单的实验和后处理程序。该方法适用于富电子和缺电子邻苯二胺。
• A New and Efficient Procedure for Synthesis of 1,5-Benzodiazepine Derivatives in Solution and under Solvent-Free Conditions
  作者：Khodayar Gholivand、Karim Zare、Hadi Jafari、Hadi Adibi

  DOI：10.1002/cjoc.201190239

  日期：2011.6

  Borax/phosphorous oxychloride (BPO) efficiently catalyzes the preparation of 1,5‐benzodiazepine derivatives of o‐phenylenediamines and ketones in solvent‐free and solution conditions. The reaction proceeds efficiently under ambient conditions giving excellent yields of the products. This new protocol allows the recycling of catalyst with no loss in its potency.

  硼砂/三氯氧化磷（BPO）在无溶剂和溶液条件下有效催化邻苯二胺和酮的1,5-苯二氮杂卓衍生物的制备。该反应在环境条件下有效地进行，从而得到优异的产物收率。该新方案允许催化剂的回收而不会损失其效力。
• Highly Efficient Zinc Oxide Nanoparticles Catalyzed Green Synthesis of 1,5-Benzodiazepines under Solvent-Free Path
  作者：Yuhao Zhao、Xuejie Yu、Manpreet Saini、Yanxu Ma、Rajesh K. Singh

  DOI：10.14233/ajchem.2014.18319

  日期：——

  An efficient and simple environment-friendly method for the preparation of substituted 1,5-benzodiazepines as biologically interesting compounds under heterogenous catalyst is described. The one-pot multicomponent condensation of o-phenylene-diamine and substituted ketones catalyzed by zinc oxide nanoparticles (ZnO NPs) under microwave under solvent-free condition has been developed. The present protocol provides a green and improved pathway for the synthesis of 1,5-benzodiazepines in terms of excellent yields, short reaction times and reusability of catalyst.

  本研究介绍了一种在异源催化剂作用下制备具有生物活性的取代 1,5-苯并二氮杂卓的高效、简便、环保的方法。在微波无溶剂条件下，开发了氧化锌纳米颗粒（ZnO NPs）催化邻苯二胺和取代酮的单锅多组分缩合反应。本方案为合成 1,5-苯并二氮杂卓提供了一条绿色的改进途径，具有产率高、反应时间短和催化剂可重复使用等优点。
• Ferrocene anchored activated carbon as a versatile catalyst for the synthesis of 1,5-benzodiazepines <i>via</i> one-pot environmentally benign conditions
  作者：Suman Kusuma、Komal N. Patil、Puneethkumar M. Srinivasappa、Nitin Chaudhari、Ajay Soni、Walid Nabgan、Arvind H. Jadhav

  DOI：10.1039/d2ra00202g

  日期：——

  1,5-Benzodiazepine is considered as one of the central moieties in the core unit of most drug molecules.

  1,5-苯二氮卓被认为是大多数药物分子核心单元的中心部分之一。
• 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.