3-methylbenzothioic S-acid | 50684-45-2

• 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-methylbenzothioic S-acid
• 英文别名: 3-Methylthiobenzoic acid；3-methylbenzenecarbothioic S-acid
• CAS: 50684-45-2
• 化学式: C₈H₈OS
• 分子量: 152.217
• InChiKey: KUUBHOLGHXMYGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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-methylbenzothioic S-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-methylbenzenecarbothioate
  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：

  间甲基苯甲酰氯 在 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 反应 3.5h， 生成 3-methylbenzothioic S-acid
  参考文献：
  名称：

  铑催化硫代酸向末端丙二烯的区域选择性加成：对映选择性获得支链烯丙基硫酯

  摘要：

  据报道，在手性支链烯丙基硫酯的原子经济合成中，铑催化的末端丙二烯与硫代酸的区域选择性和对映选择性氢硫醇化反应。通过使用铑( I )催化剂体系，末端丙二烯和硫代酸的多样性提供了相应的支链硫酯，具有优异的区域选择性、高收率和良好的对映选择性。该方法还探索了 Fmoc 保护的氨基硫代酸，用于非对映选择性合成相应的硫酯。

  DOI：

  10.1039/d1cc06470c

文献信息

• CORTICOSTEROID LINKED BETA-AGONIST COMPOUNDS FOR USE IN THERAPY
  申请人：Baker William R.

  公开号：US20090318396A1

  公开（公告）日：2009-12-24

  New chemical entities which comprise corticosteroids and phosphorylated β-agonists for use in therapy and compositions comprising and processes for preparing the same.

  新的化学实体包括皮质类固醇和磷酸化的β-激动剂，用于治疗以及包含这些化学实体的组合物和制备它们的方法。
• 2-(2,6-dichlorophenyl)-diarylimidazoles
  申请人：——

  公开号：US20030199691A1

  公开（公告）日：2003-10-23

  1 The invention is directed to compounds of formula (I), which are valuable therapeutics for the treatment of cancer and related diseases.

  这项发明涉及到式(I)的化合物，这些化合物对于治疗癌症和相关疾病非常有价值。
• Catalyst- and organic solvent-free synthesis of thioacids in water
  作者：Mohamed Elagawany、Lamees Hegazy、Bahaa Elgendy

  DOI：10.1016/j.tetlet.2019.06.061

  日期：2019.7

  acyl benzotriazoles and sodium hydrosulfide in water at room temperature. The new methodology features mild reaction conditions, high yields, short reaction times, and does not involve the use of organic solvents or bases. The reaction is eco-friendly, and the workup procedure is simple and does not require chromatographic separation.

  在室温下，由水中易得的酰基苯并三唑和氢硫化钠可高产率合成硫代酸和硫代氨基酸。新方法的特点是反应条件温和，收率高，反应时间短，并且不涉及有机溶剂或碱的使用。该反应是环境友好的，并且后处理步骤简单并且不需要色谱分离。
• Copper-Catalyzed Synthesis of Benzo[<i>b</i>]thiophenes and Benzothiazoles Using Thiocarboxylic Acids as a Coupling Partner
  作者：Hui Yu、Meishu Zhang、Yuzhe Li

  DOI：10.1021/jo401353w

  日期：2013.9.6

  copper-catalyzed approach to benzo[b]thiophene and benzothiazole derivatives using thiocarboxylic acids as a sulfur source has been developed. In the presence of CuI and 1,10-phen, and n-Pr3N as the base, (2-iodobenzyl)triphenylphosphonium bromide and (2-iodophenylimino)triphenylphosphorane reacted smoothly with thiocarboxylic acids to give benzo[b]thiophene and benzothiazole derivatives in good yields via

  已经开发出一种有效的铜催化方法，以硫代羧酸作为硫源，用于苯并[ b ]噻吩和苯并噻唑衍生物。在CuI和1,10-phen和n -Pr 3 N为碱的情况下，（2-碘苄基）三苯基溴化and和（2-碘苯基亚氨基）三苯基phosph与硫代羧酸平稳反应，生成苯并[ b ]噻吩和苯并噻唑通过顺序的Ullmann型C–S键耦合和Wittig缩合，可以得到高收率的衍生物。
• A Convenient Synthesis of<i>S</i>-Acyl Phenylselenosulfides
  作者：Takeshi Toru、Masanao Nishigaki、Takuya Seko、Toshiya Kanefusa、Eturô Maekawa

  DOI：10.1055/s-1985-31369

  日期：——

  S-Acyl arylselenosulfides 3, sulfur-selenium analogs of peroxoic esters, are prepared from thiocarboxylic acids 1 and N-phenylselenophthalimide (2).

  S-酰基芳基硒硫醚3，过氧酸酯的硫-硒类似物，由硫代羧酸1和N-苯基硒代邻苯二甲酰亚胺（2）制备。