2-(2-thienylthiomethyl)benzoic acid | 1211-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-thienylthiomethyl)benzoic acid
• 英文别名: 2--benzoesaeure；2-(2-Thienylthiomethyl)-benzoesaeure；2-thiophen-2-ylsulfanylmethyl-benzoic acid；Benzoic acid, 2-[(2-thienylthio)methyl]-；2-(thiophen-2-ylsulfanylmethyl)benzoic acid
• CAS: 1211-23-0
• 化学式: C₁₂H₁₀O₂S₂
• 分子量: 250.342
• InChiKey: HRMXQCCXQDMTHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-thienylthiomethyl)benzoic acid 在 sodium azide 、 氯甲酸乙酯 、 三乙胺 作用下， 生成 2-(Thiophen-2-ylsulfanylmethyl)-benzoyl azide
  参考文献：
  名称：

  Daich, Abdelali; Povazanec, Frantisek; Decroix, Bernard, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 8, p. 1911 - 1915

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl 2-(thiophen-2-ylsulfanylmethyl)benzoate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以1.14 g的产率得到2-(2-thienylthiomethyl)benzoic acid
  参考文献：
  名称：

  [EN] INHIBITORS OF SARS-COV-2
  [FR] INHIBITEURS DU SARS-COV-2

  摘要：

  Described herein are compounds, and methods for the treatment of coronavirus infection.

  公开号：

  WO2023122260A2

文献信息

• Antiaminic agents derived from thieno[2,3-c]-2-benzothiepin: 4-(1-Methyl-4-piperidylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin and some related compounds
  作者：Zdeněk Polívka、Miroslav Rajšner、Jan Metyš、Jiří Holubek、Emil Svátek、Miroslav Ryska、Miroslav Protiva

  DOI：10.1135/cccc19830623

  日期：——

  In the reaction of thieno[2,3c]-2-benzothiepin-4(9H)-one (VI) with 1-methyl-4-piperidylmagnesium chloride 7-(1-methyl-4-piperidyl)thieno[2,3-c]-2-benzothiepin-4(9H)-one (VIII) is formed in addition to the expected amino alcohol VII. The title compound I was obtained by the acid catalyzed dehydration of the pure alcohol VII. Compound I (pipethiadene) has outstanding antihistamine, antiserotonin, antireserpine and anticataleptic activity and was recommended to clinical trials as a potential antimigraine agent. For pharmacokinetic and metabolic studies there were prepared the NC²H₃ analogue of pipethiadene IV and further, as potential metabolites, the demethyl analogue III, S-oxide X, demethyl S-oxide XI, N-oxide XIII and N,S-dioxide XIV. The Witting reaction of the ketone VI with 3-dimethylaminopropylidenetriphenylphosphorane resulted in a mixture of geometric isomers of 4-(3-dimethylamino-propylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin with the strongly predominating Z-isomer XVI which was isolated from the mixture by crystallization of the hydrogen maleate. The mixture with the predominating Z-isomer XVI was converted by the treatment with 80% sulfuric acid and dilution with water to a mixture with the predominating E-isomer XV (dithiadene) which was isolated by crystallization of the hydrogen sulfate. Some further new thieno[2,3-c]-2-benzothiepin derivatives were synthesized as potential intermediates.

  在thieno[2,3c]-2-benzothiepin-4(9H)-one(VI)和1-甲基-4-哌啶基镁氯反应中，除了预期的氨基醇VII外，还形成了7-(1-甲基-4-哌啶基)thieno[2,3-c]-2-benzothiepin-4(9H)-one(VIII)。通过纯醇VII的酸催化脱水，得到了标题化合物I（pipethiadene）。化合物I具有出色的抗组胺、抗血清素、抗利血平和抗痉挛活性，并被推荐作为潜在的抗偏头痛药物进行临床试验。为了进行药代动力学和代谢研究，制备了pipethiadene的NC2H3类似物IV以及作为潜在代谢物的去甲基类似物III、S-氧化物X、去甲基S-氧化物XI、N-氧化物XIII和N，S-二氧化物XIV。ketoneVI与3-二甲基氨基丙烯基三苯基膦反应，得到4-(3-二甲基氨基丙烯基)-4,9-二氢thieno[2,3-c]-2-benzothiepin的几何异构体混合物，其中强烈占优势的是Z-异构体XVI，通过氢男酸盐结晶从混合物中分离出来。通过80%的硫酸处理和稀释水，将占优势的混合物转化为占优势的E-异构体XV（dithiadene），并通过硫酸氢盐结晶分离。还合成了一些新的thieno[2,3-c]-2-benzothiepin衍生物作为潜在的中间体。
• POLIVKA, Z.;RAJSNER, M.;METYS, J.;HOLUBEK, J.;SVATEK, E.;RYSKA, M.;PROTIV+, COLLECT. CZECH. CHEM. COMMUN., 1983, 48, N 2, 623-641
  作者：POLIVKA, Z.、RAJSNER, M.、METYS, J.、HOLUBEK, J.、SVATEK, E.、RYSKA, M.、PROTIV+

  DOI：——

  日期：——
• JILALE, ABDERRAHIM;DECROIX, BERNARD;MOREL, JEAN, CHEM. SCR., 27,(1987) N 3, 423-428
  作者：JILALE, ABDERRAHIM、DECROIX, BERNARD、MOREL, JEAN

  DOI：——

  日期：——