2-methyl-2,4-di(thiophen-2',2''-yl)-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-methyl-2,4-di(thiophen-2',2''-yl)-2,3-dihydro-1H-benzo[b][1,4]diazepine
• 英文别名: 2-methyl-2,4-di(thiophen-2-yl)-2,3-dihydro-1H-benzo-[b][1,4]diazepine；2-methyl-2,4-di(thiophen-2-yl)-2,3-dihydro-1H-benzo[b][1,4]diazepine；2-methyl-2,4-bis(thiophen-2-yl)-2,3-dihydro-1H-1,5-benzodiazepine；2,4-bis(2-thiophenyl)-2-methyl-2,3-dihydro-1H-1,5-benzodiazepine；2-methyl-2,4-di(2-thienyl)-2,3-dihydro-1H-1,5-benzodiazepine；2-methyl-2,4-dithiophen-2-yl-1,3-dihydro-1,5-benzodiazepine
• 化学式: C₁₈H₁₆N₂S₂
• 分子量: 324.47
• InChiKey: MBCNBYULGGXJNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.9
• 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(thiophen-2',2''-yl)-2,3-dihydro-1H-benzo[b][1,4]diazepine 、 二乙基二氯化锡 以 苯 为溶剂， 反应 2.0h， 以40%的产率得到[2-methyl-2,4-di(thiophen-2',2''-yl)-2,3-dihydro-1H-benzo[b][1,4]diazepine][Et₂SnCl₃]
  参考文献：
  名称：

  A new benzodiazepine molecule and its interactions with diorganotin(IV)chlorides

  摘要：

  2-Methyl-2,4-di-thiophen-2',2 ''-yl-2,3-dihydro-1H-benzo[b][1,4]diazepine (L) has been synthesized through condensation of phenylene-1,2-diamine and 2-acetylthiophene, and its reactions with dialkyltin(IV)dichlorides have been studied. Two salts formulated as (LH)[R2SnCl3] (R = Et, 1; R = Me, 2) have been isolated. L and 1 were structurally characterized. The conformation of the benzodiazepine L, changes in 1 due to H-bonds formation. [Et2SnCl3](-) is one of the rare examples of five coordinated tin(IV) species and has distorted trigonal bipyramidal geometry. H-bonding interactions, in 1, lead to the formation of supramolecular helices. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.09.055
• 作为产物：
  描述：

  2-乙酰基噻吩 、 邻苯二胺 在 三聚氯氰 作用下， 以 甲醇 为溶剂， 反应 26.0h， 以96%的产率得到2-methyl-2,4-di(thiophen-2',2''-yl)-2,3-dihydro-1H-benzo[b][1,4]diazepine
  参考文献：
  名称：

  在温和条件下高效TTC催化的1,5-苯并二氮杂pine衍生物的合成。

  摘要：

  2,4,6-三氯-1,3,5-三嗪（TCT）有效地催化1,2-二胺与各种可烯醇化的酮之间的缩合反应，从而以良好或优异的收率得到1,5-苯并二氮杂pine。简单和温和的反应条件，使用廉价的催化剂以及易于后处理和分离是该方法的显着特征。

  DOI：

  10.3390/molecules13092313

文献信息

• A Green Synthesis of 1,5-Benzodiazepines using Reusable-Heterogeneous Silica Sulfuric Acid Catalyst under Solvent-Free Conditions and their Antileukemic Activity
  作者：Kachigere B. Harsha、Chandagirikoppal V. Kavitha、Toreshettahally R. Swaroop、Shobith Rangappa、Kanchugarakoppal S. Rangappa

  DOI：10.14233/ajchem.2021.23103

  日期：——

  ketones containg α-hydrogen atoms by means of simple cyclocondensation via sp3 C-H activation promoted by an efficient heterogeneous silica sulfuric acid catalyst. Eco-friendliness, good yields, easy workup, reusable catalyst, short reaction times, high atom economy and solvent-free conditions are the noteworthy features of this protocol. These benzodiazepines are chosen for the evaluation of antiproliferative

  1,5-苯并二氮杂卓衍生物很容易由邻苯二胺和含有 α-氢原子的酮通过简单的环缩合，通过有效的非均相二氧化硅硫酸催化剂促进的 sp3 CH 活化来组装。该方案的显着特点是生态友好、收率高、后处理简单、催化剂可重复使用、反应时间短、原子经济性高和无溶剂条件。选择这些苯二氮卓类药物来评估针对不同白血病细胞系的抗增殖活性。在所研究的化合物中，3g 是针对所有测试的细胞系的最佳抗增殖剂。此外，目前的初步分析表明，化合物 3g 磷酸化 ERK1/2 并诱导 K562 细胞中 G1 期阻滞
• 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）。
• The facile syntheses of 2,3-dihydro-1H-1,5-benzodiazepines and their ribofuranosides
  作者：Renuka Jain、Tripti Yadav、Manoj Kumar、Ashok K. Yadav

  DOI：10.1002/jhet.365

  日期：——

  The facile syntheses of 2,3‐dihydro‐1H‐benzodiazepines containing heterocyclic moieties and their ribofuranosides have been accomplished in ionic liquids at ambient temperature. The characterization of all these compounds has been done unambiguously by IR, 1H NMR, 13C NMR, GC‐MS spectroscopy, and elemental analysis. J. Heterocyclic Chem., (2010).

  含有杂环基团的2,3-二氢-1H-苯并二氮杂及其核呋喃糖苷的简便合成已在环境温度下的离子液体中完成。通过IR，1 H NMR，13 C NMR，GC-MS光谱和元素分析明确地完成了所有这些化合物的表征。J.杂环化​​学。（2010）。
• NBS as an efficient catalyst for the synthesis of 1,5-benzodiazepine derivatives under mild conditions
  作者：Chun-Wei Kuo、Shivaji V. More、Ching-Fa Yao

  DOI：10.1016/j.tetlet.2006.09.128

  日期：2006.11

  Various biologically important 1,5-benzodiazepine derivatives were efficiently synthesized in excellent yields using catalytic amounts of NBS (10 mol %). This inexpensive, nontoxic, and readily available catalyst efficiently catalyzes the condensation of several aromatic as well as aliphatic ketones with substituted o-phenylenediamines.

  使用催化量的NBS（10 mol％），以优异的产率有效地合成了各种生物学上重要的1,5-苯并二氮杂pine衍生物。这种廉价，无毒且易于获得的催化剂有效地催化了几种芳香族以及脂肪族酮与取代的邻苯二胺的缩合。
• Efficient TCT-catalyzed Synthesis of 1,5-Benzodiazepine Derivatives under Mild Conditions
  作者：Chun-Wei Kuo、Chun-Chao Wang、Veerababurao Kavala、Ching-Fa Yao

  DOI：10.3390/molecules13092313

  日期：——

  2,4,6-Trichloro-1,3,5-triazine (TCT) efficiently catalyzed the condensation reactions between 1,2-diamines and various enolizable ketones to afford 1,5-benzodiazepines in good to excellent yields. Simple and mild reaction conditions, the use of a cheap catalyst and easy workup and isolation are notable features of this method.

  2,4,6-三氯-1,3,5-三嗪（TCT）有效地催化1,2-二胺与各种可烯醇化的酮之间的缩合反应，从而以良好或优异的收率得到1,5-苯并二氮杂pine。简单和温和的反应条件，使用廉价的催化剂以及易于后处理和分离是该方法的显着特征。