3-Chloro-benzo[b]thiophene-2-carboxylic acid [1-phenyl-meth-(E)-ylidene]-hydrazide | 144604-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-Chloro-benzo[b]thiophene-2-carboxylic acid [1-phenyl-meth-(E)-ylidene]-hydrazide
• 英文别名: N-(benzylideneamino)-3-chloro-1-benzothiophene-2-carboxamide
• CAS: 144604-95-5
• 化学式: C₁₆H₁₁ClN₂OS
• 分子量: 314.795
• InChiKey: RGUIALPNHIAJNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Chloro-benzo[b]thiophene-2-carboxylic acid [1-phenyl-meth-(E)-ylidene]-hydrazide 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以72%的产率得到2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Convenient preparation of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles promoted by Dess–Martin reagent

  摘要：

  2,5-Disubstituted 1,3,4-oxadiazoles have been conveniently prepared by oxidative cyclization of N-acyl-N'-aryliden-hydrazines promoted by all excess or Dess-Martin periodinane under Mild conditions (23 examples, up to 92% isolated yields). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.054
• 作为产物：
  描述：

  3-氯苯并ób]噻酚-2-羰酰氯 在 一水合肼 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 3-Chloro-benzo[b]thiophene-2-carboxylic acid [1-phenyl-meth-(E)-ylidene]-hydrazide
  参考文献：
  名称：

  由苯并[b]噻吩衍生的恶二唑、噻二唑和三唑的合成。

  摘要：

  在这项工作中，3-氯-2-氯羰基苯并[b]噻吩(1)由肉桂酸制备，然后转化为酰肼2。偶氮甲碱3a-e由相应的芳基醛和酰肼2制备。化合物2与甲酸反应得到N-甲酰酰肼4，其与五氧化二磷或五硫化二磷在二甲苯中回流，得到相应的2-(3-氯-1-苯并噻吩-2-基)-1,3,4 -恶二唑(5)和2-(3-氯-1-苯并噻吩-2-基)-1,3,4-噻二唑(6)。1-氨基硫脲 7 与 NaOH 反应导致闭环，得到 5-(3-氯-1-苯并噻吩-2-基)-4H-三唑-3-硫醇 (8)，将其转化为多种衍生物 9-12 2与异硫氰酸苯酯和NaOH反应得到5-(3-氯-1-苯并噻吩-2-基)-4-(苯基)-4H-1,2,4-三唑-3-硫醇(14)。

  DOI：

  10.3390/10091161

文献信息

• Novel Benzo[b]thienylhydrazine and 1,3,4-Oxadiazole Derivatives as Potential Antidepressant Agents
  作者：Omaima M. Aboulwafa、Mona A. E. El-Metwalli

  DOI：10.1002/ardp.19923250915

  日期：——

  series of benzo[b]thiophene derivatives bearing various hydrazone, hydrazine and 1,3,4‐oxadiazole moieties were synthesized as potential antidepressant agents. 22 Compounds were evaluated for their in vitro inhibitory effect on monoamine oxidase enzyme (MAO) type A. Several compounds inhibited MAO stronger than pargyline hydrochloride. Maximum inhibitions of 83% and 90% were observed with 1‐benzyl‐2

  合成了三个具有各种腙、肼和 1,3,4-恶二唑部分的新型苯并 [b] 噻吩衍生物作为潜在的抗抑郁药。评估了 22 种化合物对 A 型单胺氧化酶 (MAO) 的体外抑制作用。几种化合物对 MAO 的抑制作用强于盐酸帕吉林。1-苄基-2-(3-氯苯并[b]噻吩基-2-羰基)肼(24)和1-[2-(4-氯苯基)乙基]-2-的最大抑制率为83%和90% (3-氯苯并[b]噻吩基-2-羰基)肼(35)。
• Synthesis of Oxadiazoles, Thiadiazoles and Triazoles Derived from Benzo[b]thiophene
  作者：A. Sharba、R. Al-Bayati、M. Aouad、N. Rezki

  DOI：10.3390/10091161

  日期：——

  In this work 3-chloro-2-chlorocarbonylbenzo[b]thiophene (1) was prepared from cinnamic acid and then converted into the acid hydrazide 2. The azomethines 3a-e were prepared from the corresponding aryl aldehydes and the acid hydrazide 2. Treatment of compound 2 with formic acid gave the N-formyl acid hydrazide 4, which upon refluxing with phosphorous pentoxide or phosphorous pentasulphide in xylene

  在这项工作中，3-氯-2-氯羰基苯并[b]噻吩(1)由肉桂酸制备，然后转化为酰肼2。偶氮甲碱3a-e由相应的芳基醛和酰肼2制备。化合物2与甲酸反应得到N-甲酰酰肼4，其与五氧化二磷或五硫化二磷在二甲苯中回流，得到相应的2-(3-氯-1-苯并噻吩-2-基)-1,3,4 -恶二唑(5)和2-(3-氯-1-苯并噻吩-2-基)-1,3,4-噻二唑(6)。1-氨基硫脲 7 与 NaOH 反应导致闭环，得到 5-(3-氯-1-苯并噻吩-2-基)-4H-三唑-3-硫醇 (8)，将其转化为多种衍生物 9-12 2与异硫氰酸苯酯和NaOH反应得到5-(3-氯-1-苯并噻吩-2-基)-4-(苯基)-4H-1,2,4-三唑-3-硫醇(14)。
• Convenient preparation of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles promoted by Dess–Martin reagent
  作者：Cristian Dobrotă、Codruţa C. Paraschivescu、Ioana Dumitru、Mihaela Matache、Ion Baciu、Lavinia L. Ruţă

  DOI：10.1016/j.tetlet.2009.02.054

  日期：2009.4

  2,5-Disubstituted 1,3,4-oxadiazoles have been conveniently prepared by oxidative cyclization of N-acyl-N'-aryliden-hydrazines promoted by all excess or Dess-Martin periodinane under Mild conditions (23 examples, up to 92% isolated yields). (C) 2009 Elsevier Ltd. All rights reserved.
• Rakesh, Chawla; Anshu, Arora; Parameswaran, Manoj Kumar, Acta poloniae pharmaceutica, 2010, vol. 67, # 3, p. 247 - 253
  作者：Rakesh, Chawla、Anshu, Arora、Parameswaran, Manoj Kumar、Sharma, Prabodh Chander、Michael, Sukumar、Ravi, Thengungal Kochupappy

  DOI：——

  日期：——