2-methyl-2,4-di(4-fluorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine | 866818-05-5

• 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-methyl-2,4-di(4-fluorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine
• 英文别名: 2,4-bis(4-fluorophenyl)-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine；2-methyl-2,4-bis(4-fluorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine；2,4-Bis(4-fluorophenyl)-2-methyl-2,3-dihydro-1H-1,5-benzodiazepine；2,4-bis(4-fluorophenyl)-2-methyl-1,3-dihydro-1,5-benzodiazepine
• CAS: 866818-05-5
• 化学式: C₂₂H₁₈F₂N₂
• 分子量: 348.395
• InChiKey: KJXJTLZPVKUSJH-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  464.1±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-2,4-di(4-fluorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine 在 4-hydroxy-2,6-diphenyl-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide 、 diallyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 、 sodium sulfate 作用下， 以 氯仿 为溶剂， 反应 132.0h， 生成 、 、 (2S,4S)-2,4-bis(4-fluorophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine 、 (2S,4R)-2,4-bis(4-fluorophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine
  参考文献：
  名称：

  Dynamic kinetic asymmetric transfer hydrogenation of racemic 2,4-diaryl-2,3-dihydrobenzo[b][1,4]diazepines catalyzed by chiral phosphoric acids

  摘要：

  Dynamic kinetic Transfer hydrogenation reaction of 2-methyl-2,4-diaryl-2,3-dihydrobenzo[b][1,4]diazepines, using phosphoric acids as catalysts and Hantzsch ester as hydride source, has been studied. A 3,3'-H8-binol derived phosphoric acid has been identified the optimal chiral catalyst for this transformation, affording 1,3-diamine derivatives with up to 8/1 dr, 86% ee and 94% ee for the major and minor diastereomers, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.039
• 作为产物：
  描述：

  4-氟苯乙酮 、 邻苯二胺 在 ferrocene anchored activated carbon 作用下， 反应 8.0h， 以88%的产率得到2-methyl-2,4-di(4-fluorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine
  参考文献：
  名称：

  二茂铁锚定活性炭作为通过一锅环保条件合成 1,5-苯二氮卓类的多功能催化剂

  摘要：

  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。

  DOI：

  10.1039/d2ra00202g

文献信息

• Ceric Ammonium Nitrate (CAN) Promoted Efficient Synthesis of 1,5-Benzodiazepine Derivatives
  作者：Srinivas Adapa、Ravi Varala、Ramu Enugala、Sreelatha Nuvula

  DOI：10.1055/s-2006-939066

  日期：——

  Ceric ammonium nitrate was found to be an efficient reagent for the preparation of 1,5-benzodiazepine derivatives of a wide range of substituted o-phenylenediamines and electronically divergent ketones in moderate to excellent isolated yields (60-98%) under mild conditions using methanol as solvent at ambient temperature.

  发现硝酸铈铵是一种有效试剂，可在温和条件下使用甲醇以中等至极好的分离产率 (60-98%) 制备各种取代的邻苯二胺和电子发散酮的 1,5-苯二氮卓衍生物在环境温度下作为溶剂。
• Synergistic catalysis by an aerogel supported ionic liquid phase (ASILP) in the synthesis of 1,5-benzodiazepines
  作者：Rajanikant Kurane、Jagannath Jadhav、Sharanabasappa Khanapure、Rajashri Salunkhe、Gajanan Rashinkar

  DOI：10.1039/c3gc40592c

  日期：——

  An ionic liquid film of [Bmim]Cl containing an organometallic catalyst (Cp2ZrCl2) has been anchored on the porous matrix of an aerogel by adsorption interactions. The synthesized aerogel supported ionic liquid phase catalyst was successfully employed in the synthesis of medicinally relevant 1,5-benzodiazepines.

  含有有机金属催化剂（Cp2ZrCl2）的[Bmim]Cl离子液体膜通过吸附相互作用固定在气凝胶的多孔基质上。合成的负载型离子液体相催化剂气凝胶成功应用于具有药学相关性的1,5-苯二氮杂䓬的合成。
• 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。
• Efficient Method for the Synthesis of 1,5‐Benzodiazepine Derivatives Catalyzed by Monoammonium Salt of 12‐Tungstophosphoric Acid
  作者：B. Y. Giri、B. L. A. Prabavathi Devi、K. Vijaya Lakshmi、R. B. N. Prasad、N. Lingaiah、P. S. Sai Prasad

  DOI：10.1080/00397910600947999

  日期：2006.12

  salt of 12‐tungstophosphoric acid [(NH4)H2PW12O40] was found to be a practical, inexpensive, reusable, and efficient heterogeneous catalyst for the preparation of 1,5‐benzodiazepine derivatives of o‐phenylenediamine and ketones. The heteropolyacid‐based catalyst has the advantages of simple workup procedure, water insolubility with good activity, and high‐yielding reaction for the synthesis of 1,5‐benzodiazepine

  摘要 12-钨磷酸单铵盐 [(NH4)H2PW12O40] 是一种实用、廉价、可重复使用且高效的多相催化剂，用于制备邻苯二胺和酮的 1,5-苯二氮卓衍生物。该杂多酸基催化剂具有后处理简单、不溶于水、活性好、合成1,5-苯二氮卓衍生物反应收率高等优点。IICT 通讯第 060112 号。
• 一种1,5-苯并二氮杂卓类化合物的合成方法
  申请人：浙江工业大学

  公开号：CN110563658B

  公开（公告）日：2021-08-24

  本发明公开了一种制备1,5‑苯并二氮杂卓类化合物的方法，所述的方法具体按如下步骤进行：将金催化剂、添加剂、式II所示的炔烃、式III所示的邻苯二胺衍生物溶于有机溶剂中置于耐压反应管中，于25℃搅拌反应6～24小时，得到反应液经后处理得到式IV所示的1,5‑苯并二氮杂卓类化合物；所述的式I所式金催化剂、添加剂、式II所示炔烃、式III所示邻苯二胺衍生物的物质的量之比为0.01～0.07:0～0.1:2.0～3.0:1。本发明所述的方法使用双功能金催化剂，使反应在室温条件下进行，节约能源消耗；有催化剂用量少，产率高，底物普适性强，操作简便等优点。