3-chlorothiobenzoic acid | 50684-49-6

• 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: 3-chlorothiobenzoic acid
• 英文别名: 3-chlorobenzenecarbothioic S-acid
• CAS: 50684-49-6
• 化学式: C₇H₅ClOS
• 分子量: 172.635
• InChiKey: CBZUINSNIXJMHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  18.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chlorothiobenzoic acid 在 potassium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.08h， 生成 S-benzamido 3-chlorobenzenecarbothioate
  参考文献：
  名称：

  Design, Synthesis, and Cardioprotective Effects of N-Mercapto-Based Hydrogen Sulfide Donors

  摘要：

  Hydrogen sulfide (H2S) is a signaling molecule which plays regulatory roles in many physiological and/or pathological processes. Therefore, regulation of H2S levels could have great potential therapeutic value. In this work, we report the design, synthesis, and evaluation of a class of N-mercapto (N-SH)-based H2S donors. Thirty-three donors were synthesized and tested. Our results indicated that controllable H2S release from these donors could be achieved upon structural modifications. Selected donors (NSHD-1, NSHD-2, and NSHD-6) were tested in cellular models of oxidative damage and showed significant cytoprotective effects. Moreover, NSHD-1 and NSHD-2 were also found to exhibit potent protective effects in a murine model of myocardial ischemia reperfusion (MI/R) injury.

  DOI：

  10.1021/acs.jmedchem.5b01033
• 作为产物：
  描述：

  3-氯苯甲酰氯 在 sodium hydrosulfide monohydrate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3-chlorothiobenzoic acid
  参考文献：
  名称：

  通过可见光促进的原子取代过程将硫代酸转化为羧酸

  摘要：

  已经开发了一种可见光促进的原子取代反应，用于以二甲亚砜 (DMSO) 作为氧源将硫代酸转化为羧酸，以超过 90% 的产率提供各种烷基和芳基羧酸。通过硫代酸和 DMSO 之间形成的氢键加合物的光化学反应，原子取代过程顺利进行。提出了涉及 DMSO 的质子耦合电子转移 (PCET) 以及同时产生硫基和羟基自由基是实现转化的关键步骤。

  DOI：

  10.1021/acs.orglett.2c00481

文献信息

• CONTROLLED CHEMICAL RELEASE OF HYDROGEN SULFIDE
  申请人：Xian Ming

  公开号：US20130253051A1

  公开（公告）日：2013-09-26

  Agents of formula: where R1 and R2 vary independently and are acyl, sulfonyl, phosphoryl, alkyl, substituted alkyl, halogen, aryl, arylalkyl, substituted aryl, heteroaryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, heterocycle, or heteroatoms; and R3 is H or a member of a ring structure which includes R2, are provided; as are agents of formula: where R1, R2 and R3 vary independently and: R1=OH, OR′, NHR′, NR′R″ (with R′ R″=alkyl, aryl, heteroaryl, etc); R 2 =acyl, alkyl, aryl, sulfonyl, etc; R3=alkyl, aryl, substituted aryl, heteroaryl, etc; and R4 and R5 are (independently) H, methyl or alkyl, substituted alkyl, aryl, substituted aryl, etc. Methods of using the agents to treat e.g. cardiovascular disease, stroke, shock, injuries caused by hypoxia, male erectile dysfunction, and Alzheimer's are provided.

  提供了公式代理人：其中R1和R2分别变化且独立，并且为酰基，磺酰基，磷酰基，烷基，取代烷基，卤素，芳基，芳基烷基，取代芳基，杂环芳基，烯基，取代烯基，炔基，取代炔基，环烷基，杂环，或杂原子; 而R3为H或包括R2的环结构的成员; 提供了公式代理人：其中R1，R2和R3独立变化且：R1 = OH，OR′，NHR′，NR′R″（其中R′ R″ = 烷基，芳基，杂环芳基等）; R2 = 酰基，烷基，芳基，磺酰基等; R3 = 烷基，芳基，取代芳基，杂环芳基等; 而R4和R5为（独立的）H，甲基或烷基，取代烷基，芳基，取代芳基等。提供了使用这些代理人治疗心血管疾病，中风，休克，缺氧引起的损伤，男性勃起功能障碍和阿尔茨海默病的方法。
• 10.1021/acs.joc.4c01087
  作者：Wang, Rui、Yuan, Jia-Long、Liang, Kun-Long、Hu, Ji-Yun、Fu, Qiang、Liang, Fu-Shun

  DOI：10.1021/acs.joc.4c01087

  日期：——

  An ambient-light-promoted stereospecific olefinic C(sp2)–S bond construction of thioacids and 1,1-diarylethenes has been demonstrated, affording various (Z)-vinyl thioesters in 51–85% yields under solvent- and catalyst-free conditions. Mechanistic studies indicated that the formation of thioacid–olefin complexes is responsible for generating a carbonyl thiyl radical and dioxygen in the air participates

  硫代酸和 1,1-二芳基乙烯的环境光促进的立体特异性烯属 C(sp 2 )–S 键结构已被证明，在无溶剂和无催化剂的情况下以 51–85% 的产率提供各种 ( Z )-乙烯基硫酯状况。机理研究表明，硫代酸-烯烃络合物的形成负责产生羰基硫基自由基，空气中的分子氧参与反应并充当无痕试剂。此外，代表性化合物3i的克级合成和聚集诱导发射特性已经证明了合成应用。
• 10.1021/acs.orglett.4c02232
  作者：Liu, Yunqi、Zhou, Xiyan、Li, Ruining、Sun, Zhankui

  DOI：10.1021/acs.orglett.4c02232

  日期：——

  gem-difluoroalkene moiety is frequently found in medicinal chemistry. From α-keton sulfides and thioic acids, we were able to develop a universal approach for the synthesis of γ,γ-difluoroallylic ketones and δ,δ-difluoroallylic ketones via a desulfurative/defluorinative alkylation process. We expect that this mild and efficient method will be complementary to other known strategies.

  偕二氟烯烃部分常见于药物化学中。从 α-酮硫化物和硫代酸，我们能够开发出一种通过脱硫/脱氟烷基化过程合成 γ,γ-二氟烯丙酮和 δ,δ-二氟烯丙酮的通用方法。我们期望这种温和而有效的方法将与其他已知策略形成补充。
• Kato, Shinzi; Oguri, Motohiro; Ishida, Masaru, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 12, p. 1585 - 1590
  作者：Kato, Shinzi、Oguri, Motohiro、Ishida, Masaru

  DOI：——

  日期：——
• Kato, Shinzi; Hattori, Eiji; Sato, Hiroyuki, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1981, vol. 36, # 7, p. 783 - 790
  作者：Kato, Shinzi、Hattori, Eiji、Sato, Hiroyuki、Mizuta, Masateru、Ishida, Masaru

  DOI：——

  日期：——