2-(4-fluorophenyl)-4-phenyl-2,3-dihydro-1,5-benzothiazepine | 86602-75-7

• 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: 2-(4-fluorophenyl)-4-phenyl-2,3-dihydro-1,5-benzothiazepine
• 英文别名: 2-(4-fluorophenyl)-4-phenyl-2,3-dihydrobenzo[b][1,4]thiazepine
• CAS: 86602-75-7
• 化学式: C₂₁H₁₆FNS
• 分子量: 333.429
• InChiKey: PUWCSGVVXVNRMY-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103 °C
• 沸点：
  467.2±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)：
  5.2
• 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：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-4-phenyl-2,3-dihydro-1,5-benzothiazepine 、 phenylhydroxamoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以37%的产率得到3a,4-dihydro-1,3a-diphenyl-5-(4-fluorophenyl)-5H-<1,2,4>oxadiazolo<5,4-d><1,5>benzothiazepine
  参考文献：
  名称：

  5H-[1,2,4]Oxadiazolo[5,4-d][1,5]benzothiazepines as anticonvulsant agents in DBA/2 mice

  摘要：

  A series of 3a,4-dihydro-5H-[1,2,4]oxadiazolo[5,4-d] [1,5]benzothiazepines have been synthesized by 1,3-dipolar cycloaddition reaction of benzonitriloxide to the C=N double bond of 1,5-benzothiazepine derivatives, and the stereochemical features of compounds obtained have been determined by NMR spectroscopy. The results of evaluation of their activity in preventing seizures induced by audiogenic stimulation in DBA/2 mice are also reported and discussed. The 5-(4-bromophenyl)1,3-diphenyl derivative 3b, the most active compound of the series, is over 20 times more active than the parent benzothiazepine Ib and shows an activity comparable to clobazam and better than desmethylclobazam.

  DOI：

  10.1016/0223-5234(96)88311-5
• 作为产物：
  描述：

  苯乙酮 在 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 2-(4-fluorophenyl)-4-phenyl-2,3-dihydro-1,5-benzothiazepine
  参考文献：
  名称：

  Synthesis, characterization, in vitro cholinesterase and hRBCs hemolysis assay and computational evaluation of novel 2,3,4,5-tetrahydrobenzothiazepine appended α-aminophosphonates

  摘要：

  DOI：

  10.1016/j.bioorg.2021.105397

文献信息

• An Improved Procedure for the Synthesis of 1,5-Benzothiazepines Using Ceric Ammonium Nitrate (CAN)
  作者：Asha V. Chate、Ratnadeep S. Joshi、Priyanka G. Mandhane、Charansingh H. Gill

  DOI：10.5012/jkcs.2011.55.5.776

  日期：2011.10.20

  A mild and efficient procedure for the synthesis of various 1,5-benzothiazepines were developed. This method provides an easy access for preparation of 1,5-benzothiazepine derivatives in the presence of 10 mol% catalyst of CAN under ultrasonic irradiation. This method provided clean conversion, mild reaction condition, no use of toxic solvent and shorter reaction time compared to other reported method.

  开发了一种温和且高效的合成多种1,5-苯并噻嗪的程序。该方法在超声波照射下使用10mol%的CAN催化剂，提供了制备1,5-苯并噻嗪衍生物的简便途径。与已报道的其他方法相比，该方法提供了清晰的转化、温和的反应条件，无需使用有毒溶剂，并且反应时间更短。
• 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。
• Microwave Assisted Synthesis of 1,5-Benzothiazepines Using Greener Reaction Medium
  作者：Sanjay S. Kotalwar、Amol D. Kale、Ram B. Kohire、Vasant B. Jagrut

  DOI：10.14233/ajchem.2019.21716

  日期：2019.4.15

  An efficient and eco-friendly synthesis of 1,5-benzothiazepines has been developed by the reaction of various 2-propen-1-ones with 2-aminothiophenol using microwave irradiation in greener reaction medium, glycerol. The clean reaction conditions, shorter reaction time, high yields and non-toxic, biodegradable reaction medium manufactured from renewable sources are unique features of this method.

  通过使用微波辐射在更环保的反应介质甘油中，将各种2-丙烯酮与2-氨基噻吩反应，开发了一种高效、环保的1,5-苯并噻吩合成方法。该方法的独特特点包括清洁的反应条件、较短的反应时间、高产率以及使用可再生来源制造的无毒、可生物降解的反应介质。
• ‘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.
• Synthesis, characterization, in vitro cholinesterase and hRBCs hemolysis assay and computational evaluation of novel 2,3,4,5-tetrahydrobenzothiazepine appended α-aminophosphonates
  作者：Sarfaraz Shaikh、Pratik Dhavan、Jasmin Uparkar、Pinky Singh、S.P. Vaidya、B.L. Jadhav、M.M.V. Ramana

  DOI：10.1016/j.bioorg.2021.105397

  日期：2021.11