dibenzothiophene-2-carboxylic acid | 20928-05-6

• 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: dibenzothiophene-2-carboxylic acid
• 英文别名: dibenzothiophene-3-carboxylic acid；2-Dibenzothiophenecarboxylic acid；Dibenzothiophen-2-carbonsaeure；Dibenzo[b,d]thiophene-2-carboxylic acid；2-Carboxy-dibenzothiophen
• CAS: 20928-05-6
• 化学式: C₁₃H₈O₂S
• 分子量: 228.271
• InChiKey: FESBZBHBDLEBID-UHFFFAOYSA-N

物化性质

• 熔点：
  253 °C
• 沸点：
  468.0±18.0 °C(Predicted)
• 密度：
  1.429±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dibenzothiophene-2-carboxylic acid 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以74%的产率得到3-苯基苯甲酸
  参考文献：
  名称：

  Desulfurization of benzo- and dibenzothiophenes with nickel boride

  摘要：

  Nickel boride, prepared from the reduction of nickel chloride hexahydrate with sodium borohydride in methanol-tetrahydrofuran, reduces benzothiophenes to alkylbenzenes and dibenzothiophenes to biphenyls. The reaction is rapid at or below room temperature and does not require protection from the atmosphere. Best results are obtained when the nickel boride is generated in situ in the presence of the sulfur compound. Hydroxyl, carboxyl, ester, and amino groups are unaffected while chloro, bromo, and nitro substituents are also reduced under these conditions. A short-lived intermediate, possibly a nickel hydride species, appears to be required in the desulfurization. Complexation of the substrate to the nickel boride surface, followed by stepwise reduction of the two C-S bonds, occurs. The faster disappearance of dibenzothiophene containing the lighter S-32 isotope compared to that with S-34 (k(S-32)/k(S-34) = 1.005 to 1.006) suggests that C-S bond cleavage is the rate-determining step.

  DOI：

  10.1021/jo00033a017
• 作为产物：
  描述：

  2-乙酰基二苯并噻吩 在 1,4-二氧六环 、 碘 、 potassium iodide 作用下， 生成 dibenzothiophene-2-carboxylic acid
  参考文献：
  名称：

  DIBENZOTHIOPHENE: ORIENTATION AND DERIVATIVES

  摘要：

  DOI：

  10.1021/jo01219a003

文献信息

• Substituted 7-aza[2.2.1]bicycloheptanes for the treatment of disease
  申请人：——

  公开号：US20030105089A1

  公开（公告）日：2003-06-05

  The invention provides compounds of Formula I: 1 which may be in the form of pharmaceutical acceptable salts or compositions, are useful in treating diseases or conditions in which &agr;7 nicotinic acetylcholine receptors (nAChRs) are known to be involved.

  这项发明提供了Formula I的化合物： 1 这些化合物可以是药用可接受的盐或组合物的形式，对治疗涉及α7尼古丁型乙酰胆碱受体(nAChRs)的疾病或症状是有用的。
• Oxidative α-C–C Bond Cleavage of 2° and 3° Alcohols to Aromatic Acids with O₂ at Room Temperature via Iron Photocatalysis
  作者：Zongnan Zhang、Guoxiang Zhang、Ni Xiong、Ting Xue、Junjie Zhang、Lu Bai、Qinyue Guo、Rong Zeng

  DOI：10.1021/acs.orglett.1c00556

  日期：2021.4.16

  cleavage of unfunctionalized secondary (2°) and tertiary alcohols (3°) is essential for valorization of macromolecules and biopolymers. We developed a blue-light-driven iron catalysis for aerobic oxidation of 2° and 3° alcohols to acids via α-C–C bond cleavages at room temperature. The first example of oxygenation of the simple tertiary alcohols was reported. The iron catalyst and blue light play critical

  未官能化的仲醇（2°）和叔醇（3°）的选择性α-CC键断裂对于大分子和生物聚合物的增值至关重要。我们开发了一种蓝光驱动的铁催化剂，用于在室温下通过α-CC键断裂将2°和3°醇有氧氧化为酸。报道了简单叔醇氧化的第一个例子。铁催化剂和蓝光起着至关重要的作用，可以使醇类形成高反应性的O自由基，并随后发生两次α-CC键断裂。
• CO₂ activation by electrogenerated divalent samarium for aryl halide carboxylation
  作者：Sakna Bazzi、Gaëtan Le Duc、Emmanuelle Schulz、Corinne Gosmini、Mohamed Mellah

  DOI：10.1039/c9ob01752f

  日期：——

  The reductive carboxylation of aryl halides has been investigated using a samarium electrode as a sacrificial anode to yield the corresponding benzoic acids, providing a smooth strategy for CO2 activation. Carboxylation occurred after an efficient reduction of carbon dioxide mediated by an electrogenerated Sm(ii)-complex acting as a strong monoelectronic reductive reagent.

  已经研究了使用a电极作为牺牲阳极来生成芳基卤化物的还原羧化反应，以产生相应的苯甲酸，从而为CO2活化提供了一种平稳的策略。在由电生成的Sm（ii）络合物充当强单电子还原剂的介导的二氧化碳的有效还原之后，发生了羧化反应。
• Cyclic sulphur compounds triazolyl substituted phenoxathin 10, 10
  申请人：Burroughs Wellcome Co.

  公开号：US04145350A1

  公开（公告）日：1979-03-20

  Certain tricyclic sulphone compounds each of which is substituted in the 1-, 2-, 3- or 4-position by a carboxyl or (5-tetrazolyl) group and each of which is optionally substituted in the 5-, 6-, 7- or 8-position by a second carboxyl or (5-tetrazolyl) group or a substituent selected from cyano, halogen, nitro, alkyl, alkoxy, acyl, amino, acylamino, thioalkyl, alkylsulphinyl and alkylsulphonyl, as well as salts, and optionally substituted esters and amides of the carboxyl substituted compounds and alkyl derivatives of the tetrazolyl substituted compounds, are useful for the relief or prophylaxis of allergic conditions.

  某些三环磺酰化合物，其中每个化合物在1-、2-、3-或4-位被羧酸或（5-四唑基）基替代，且每个化合物在5-、6-、7-或8-位可选择被第二个羧酸或（5-四唑基）基或从氰基、卤素、硝基、烷基、烷氧基、酰基、氨基、酰胺基、硫代烷基、烷基磺酰基和烷基磺酰基中选择的取代基替代，以及羧酸取代化合物和四唑基取代化合物的烷基衍生物的盐，可选择的酯和酰胺，对于缓解或预防过敏症状是有用的。
• Cyclic sulphur compounds
  申请人：Burroughs Wellcome Co.

  公开号：US04177257A1

  公开（公告）日：1979-12-04

  Certain tricyclic sulphone compounds each of which is substituted in the 1-,2-,3- or 4-position by a carboxyl or (5-tetrazolyl) group and each of which is optionally substituted in the 5-,6-,7- or 8-position by a second carboxyl or (5-tetrazolyl) group or a substituent selected from cyano, halogen, nitro, alkyl, alkoxy, acyl, amino, acylamino, thioalkyl, alkylsulphinyl and alkylsulphonyl, as well as salts, and optionally substituted esters and amides of the carboxyl substituted compounds and alkyl derivatives of the tetrazolyl substituted compounds, are useful for the relief or prophylaxis of allergic conditions.

  某些三环磺酰化合物，其中每个在1-,2-,3-或4-位被羧基或（5-四唑基）基取代，每个在5-,6-,7-或8-位可选地被第二个羧基或（5-四唑基）基或从氰基，卤素，硝基，烷基，烷氧基，酰基，氨基，酰胺基，硫代烷基，烷基磺酰基和烷基磺酰基中选择的取代基所取代，以及羧基取代化合物和四唑基取代化合物的烷基衍生物的盐，可选地取代的酯和酰胺，对于缓解或预防过敏症状是有用的。