4-(4-bromophenyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine | 64820-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: 4-(4-bromophenyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine
• 英文别名: 2-phenyl-4-(4-bromophenyl)-2,3-dihydro-1,5-benzothiazepine；4-(4-bromo-phenyl)-2-phenyl-2,3-dihydro-benzo[b][1,4]thiazepine
• CAS: 64820-47-9
• 化学式: C₂₁H₁₆BrNS
• 分子量: 394.335
• InChiKey: DBUUTQFBKDPJHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯甲酸酐 、 4-(4-bromophenyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 6.0h， 以55.6%的产率得到3-benzoyl-2-(4-bromophenyl)-2,3-dihydro-2-styrylbenzothiazole
  参考文献：
  名称：

  Oxazepines and Thiazepines XXXVII [1]. A Simple and Convenient Procedure for the Preparation of 3-Acyl-2,3-dihydrobenzothiazoles by Ring Contraction of 2,4-Diaryl-2,3-dihydro-1,5-benzothiazepines under Acylating Conditions

  摘要：

  3-Acyl-2,3-dihydrobenzothiazoles 13-30 were prepared by ring contraction of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines 1-12 under acylating conditions. This procedure provides a general and efficient access to these benzothiazole derivatives.

  DOI：

  10.1007/pl00013498
• 作为产物：
  描述：

  2,3-dihydro-2,4-diphenyl-1,5-benzothiazepine 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 4-(4-bromophenyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine
  参考文献：
  名称：

  2,4-Diaryl-2,3-dihydrobenzo[b][1,4]thiazepines

  摘要：

  DOI：

  10.1007/bf00842834

文献信息

• A practical synthesis of 2,3-dihydro-1,5-benzothiazepines
  作者：Domenico C. M. Albanese、Nicoletta Gaggero、Meng Fei

  DOI：10.1039/c7gc02097j

  日期：——

  2,3-Dihydro-1,5-benzothiazepines have been obtained through a domino process involving a Michael addition of 2-aminothiophenols to chalcones, followed by in situ cyclization. Up to 98% chemical yields have been obtained at room temperature under essentially neutral conditions by using hexafluoro-2-propanol as an efficient medium.

  已经通过多米诺法获得了2，3-二氢-1，5-苯并硫氮杂s，该方法包括将2-氨基硫酚的迈克尔加成至查耳酮，然后进行原位环化。使用六氟-2-丙醇作为有效介质，在基本上中性的室温下，室温下可获得高达98％的化学收率。
• Magnesium Perchlorate as a New and Highly Efficient Catalyst for the Synthesis of 2,3-Dihydro-1,5-benzothiazepines
  作者：Asit Chakraborti、Gopal Khatik、Raj Kumar

  DOI：10.1055/s-2007-965892

  日期：2007.2

  Commercially available magnesium perchlorate has been found to be a highly efficient catalyst for the reaction of 1,3-diarylprop-2-enones with 2-aminothiophenol leading to the synthesis of 2,3-dihydro-1,5-benzothiazepines in high yields and in short times.

  商业化的过氯酸镁被发现是一种高效的催化剂，可以促使1,3-二芳基丙-2-酮与2-氨基噻吩醇的反应，从而在短时间内以高产率合成2,3-二氢-1,5-苯噻嗪。
• Catalyst-free synthesis of 2,3-dihydro-1,5-benzothiazepines in a renewable and biodegradable reaction medium
  作者：Neetu Yadav、Vijay B. Yadav、Mohd Danish Ansari、Hozeyfa Sagir、Ankit Verma、I. R. Siddiqui

  DOI：10.1039/c8nj05611k

  日期：——

  A clean and efficient strategy for the synthesis of benzothiazepines from chalcone and ortho-aminothiophenol has been reported.

  一种从查尔酮和邻氨基硫酚合成苯噻吩的清洁高效策略已被报道。
• Synthesis and Study of Catalytic Perspectives of DABCO Based Ionic Liquid for the Synthesis of 2,3-Dihydro-1,5-Benzothiazepines and 2-Phenylbenzothiazoles
  作者：Priyanka Pinate、Sangita Makone

  DOI：10.1007/s10562-022-04033-z

  日期：2023.4

  DABCO based ionic liquids through the comparison of [H2-DABCO][HSO4]2, [H2-DABCO][H2PO4]2, [H2-DABCO][ClO4]2, and [C4H10-DABCO][HSO4]2. The proposed method displayed several advantages over prior methods, including use of non-metal and inexpensive catalyst, shorter reaction times, green solvent media, moderate to excellent product yields, easy work-up, and recyclability of the ionic liquid for subsequent

  本研究合成、表征了一种新型 DABCO 基双阳离子酸性离子液体 [C 4 H 10 -DABCO][HSO 4 ] 2 ，并将其作为一种环保且可重复使用的催化剂成功应用于合成 2,3-二氢-1,5-苯并噻氮和 2-苯基苯并噻唑衍生物。本工作通过比较[H 2 -DABCO ][HSO 4 ] 2 , [H 2 -DABCO][H 2 PO 4 ]显示了阳离子和阴离子对基于DABCO的离子液体的催化适用性和防潮性能的影响] 2 , [H 2 -DABCO][ClO 4 ]2和[C 4 H 10 -DABCO][HSO 4 ] 2。所提出的方法显示出与现有方法相比的几个优点，包括使用非金属和廉价催化剂、反应时间更短、绿色溶剂介质、中等至优异的产品收率、易于后处理以及离子液体可回收用于后续反应而无需活动大大减少。 图形概要
• ‘On water’ synthesis of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines catalysed by sodium dodecyl sulfate (SDS)
  作者：Gaurav Sharma、Raj Kumar、Asit K. Chakraborti

  DOI：10.1016/j.tetlet.2008.04.146

  日期：2008.6

  An efficient synthesis of 1,3-diaryl-2,3-dihydro-1,5-benzothiazepines has been developed by the reaction of various 1,3-diaryl-2-propenones with 2-aminothiophenol in water under neutral conditions catalysed by SDS. Excellent chemoselectivity was observed for substrates possessing halogen atoms or nitro/alkoxy/thioalkyl groups which did not undergo competitive aromatic nucleophilic substitution of the halogen atoms or the nitro group, reduction of the nitro or the a,p-unsaturated carbonyl group, or dealkylation of the alkoxy/thioalkoxy groups. (C) 2008 Elsevier Ltd. All rights reserved.