2,4-dibutyl-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-dibutyl-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine
• 英文别名: 2,4-dibutyl-2,3-dihydro-2-methyl-1H-1,5-benzodiazepine；2-methyl-2,4-dibutyl-2,3-dihydro-1H-1,5-benzodiazepine；2,4-Dibutyl-2-methyl-1,3-dihydro-1,5-benzodiazepine
• 化学式: C₁₈H₂₈N₂
• 分子量: 272.434
• InChiKey: YMMXEAGRWYVZIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-己酮 、 1-叠氮基-2-硝基苯 在 三氢化钐 、 四氯化钛 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到2,4-dibutyl-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)01888-8

文献信息

• Chitosan-supported Fe3O4 nanoparticles: a magnetically recyclable heterogeneous nanocatalyst for the syntheses of multifunctional benzimidazoles and benzodiazepines
  作者：Ali Maleki、Nakisa Ghamari、Maryam Kamalzare

  DOI：10.1039/c3ra47366j

  日期：——

  An environmentally benign and clean biopolymer-based heterogeneous nanocatalyst was prepared and its properties and morphology were characterized using scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX) and X-ray diffraction (XRD). Then, its catalytic activity was investigated in two important organic reactions. In these reactions, efficient and selective syntheses of 1,2-disubstituted benzimidazole and 1,5-benzodiazepine derivatives were carried out using 1,2-diamines and aldehydes or ketones in the presence of a catalytic amount of magnetically recoverable chitosan-supported iron oxide nanoparticles (Fe3O4/chitosan), as a biodegradable nanocomposite, in ethanol at ambient temperature in high yields. The Fe3O4/chitosan nanocatalyst can be recovered easily and reused without any significant loss of the catalytic activity.

  制备了一种环境友好且清洁的生物聚合物基异质纳米催化剂，并通过扫描电子显微镜（SEM）、能量色散X射线光谱（EDX）和X射线衍射（XRD）对其性质和形态进行了表征。随后，研究了其在两种重要有机反应中的催化活性。在这些反应中，使用1,2-二胺和醛或酮在催化量的可磁回收壳聚糖支持铁氧化物纳米颗粒（Fe3O4/壳聚糖）的存在下，在室温下的乙醇中高效且选择性地合成了1,2-取代的苯并咪唑和1,5-苯并二氮杂卓衍生物。 /壳聚糖纳米催化剂可以轻松回收并重复使用，且没有显著的催化活性损失。
• Selective synthesis of benzimidazoles and benzodiazepines catalyzed by Brønsted Acid/ base-cooperative Titanocene dichloride
  作者：Mengyuan Zhuang、Li Tu、Ya Wu、Yajun Jian、Yanyan Wang、Weiqiang Zhang、Huaming Sun、Ziwei Gao

  DOI：10.1016/j.mcat.2022.112181

  日期：2022.5

  o-phenylenediamine and carbonyl compounds by Brønsted acid/base assisted titanocene dichloride. Mechanism research including NMR and ESI-MS analyses and control experiments elucidated the new catalytic species formed by Cp2TiCl2 and the combination of titanocene Lewis acid with Brønsted acid/base was responsible for selective transformations of aldehyde and ketone with o-phenylenediamine into benzimidazole

  苯并咪唑和苯二氮卓类化合物是由邻苯二胺和羰基化合物通过布朗斯台德酸/碱辅助二氯化二茂钛选择性合成的。包括 NMR 和 ESI-MS 分析和控制实验在内的机理研究阐明了由 Cp 2 TiCl 2形成的新催化物质，二茂钛路易斯酸与布朗斯台德酸/碱的组合负责将醛和酮与邻苯二胺选择性转化为苯并咪唑和苯二氮卓类药物。
• Zhong; Zhang; Chen, Journal of Chemical Research - Part S, 2000, # 11, p. 532 - 534
  作者：Zhong、Zhang、Chen

  DOI：——

  日期：——
• Gold(I)-Catalyzed Synthesis of 1,5-Benzodiazepines Directly from <i>o</i>-Phenylenediamines and Alkynes
  作者：Jianqiang Qian、Yunkui Liu、Jianhai Cui、Zhenyuan Xu

  DOI：10.1021/jo300543n

  日期：2012.5.4

  A unique gold(I)-catalyzed highly atom-economic synthesis of 1,5-benzodiazepines directly from o-phenylenediamines and alkynes has been achieved for the first time.
• Terminal alkynes as keto-methyl equivalent toward one pot synthesis of 1,5-benzodiazepine derivatives under catalysis of Hg(OTf)2
  作者：Gourhari Maiti、Utpal Kayal、Rajiv Karmakar、Rudraksha N. Bhattacharya

  DOI：10.1016/j.tetlet.2012.01.036

  日期：2012.3

  Mercuric triflate catalyzes the reaction between 1,2-diaminobenzene and terminal alkynes to afford 2,4-disubstituted 2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine in an excellent yield. The terminal alkynes function as a source of keto-methyl equivalent. (C) 2012 Elsevier Ltd. All rights reserved.