5-chloro-2-mercapto-benzoic acid methyl ester | 52948-10-4

• 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: 5-chloro-2-mercapto-benzoic acid methyl ester
• 英文别名: 5-Chlor-2-mercapto-benzoesaeure-methylester；methyl 5-chloro-2-mercaptobenzoate；methyl 5-chloro-2-sulfanylbenzoate
• CAS: 52948-10-4
• 化学式: C₈H₇ClO₂S
• 分子量: 202.661
• InChiKey: VRBWQNKOHVYWTK-UHFFFAOYSA-N

物化性质

• 熔点：
  45-47 °C
• 沸点：
  110-112 °C(Press: 0.5 Torr)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-2-mercapto-benzoic acid methyl ester 在 氢氧化钾 、 hydroxylamine-O-sulfonic acid 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 5-氯-1,2-苯异噻唑-3(2H)-酮
  参考文献：
  名称：

  A Facile Synthesis of 1,2-Benzisothiazolin-3-ones from Thiosalicylates

  摘要：

  Synthesis of 1,2-benzisothiazolin-3-ones by cyclization of 2-sulfenamoylbenzoates, which were prepared from amination of thiosalicylates by hydroxylamine-O-sulfonic acid, was examined. Although treatment of methyl 2-sulfenamoylbenzoate on heating gave unexpected 2-(2-methoxycarbonylphenylthio)-1,2-benzisothiazolin-3-one, the treatment with base at room temperature afforded 1,2-benzisothiazolin-3-one in a good yield.

  DOI：

  10.3987/com-99-8706
• 作为产物：
  描述：

  5-氯-2-巯基苯甲酸 在 盐酸 作用下， 生成 5-chloro-2-mercapto-benzoic acid methyl ester
  参考文献：
  名称：

  163.氧杂蒽酮和噻吨酮。第二部分 噻吨氧基，9-蒽胺和9-噻吨胺的衍生物

  摘要：

  DOI：

  10.1039/jr9510000757

文献信息

• 5-methylthio-3-hydroxybenzo [b]thiophene-2-carboxamide derivatives as
  申请人：Merck & Co., Inc.

  公开号：US04800211A1

  公开（公告）日：1989-01-24

  3-Hydroxybenzo[b]thiophene-2-carboxamide derivatives have been prepared by: (1) treating a substituted 2-halobenzoate with a thioacetamide. (2) treating a substituted thiosalicylate with an appropriately substituted haloacetamide; and (3) further synthetic modification of compounds prepared above. These compounds have been found to be effective inhibitors of both cyclooxygenase and lipoxygenase and thereby useful in the treatment of pain, fever, inflammation, arthritic conditions, asthma, allergic disorders, skin diseases, cardiovascular disorders, psoriasis, inflammatory bowel disease, glaucoma or other prostaglandins and/or leukotriene mediated diseases.

  3-羟基苯并[b]噻吩-2-甲酰胺衍生物已通过以下方法制备：(1)用硫代乙酰胺处理取代的2-卤代苯甲酸酯。(2)用适当取代的卤代乙酰胺处理取代的硫代水杨酸酯；以及(3)对上述制备的化合物进行进一步的合成修饰。已发现这些化合物对环氧化酶和脂氧合酶均具有有效抑制作用，因此在治疗疼痛、发热、炎症、关节炎、哮喘、过敏性疾病、皮肤病、心血管疾病、银屑病、炎症性肠病、青光眼或其他前列腺素和/或白三烯介导的疾病治疗中具有用处。
• Über Dibenzo-thiazepin-Derivate und ihre pharmakologische Wirkung
  作者：R. Jaques、A. Rossi、E. Urech、H. J. Bein、K. Hoffmann

  DOI：10.1002/hlca.19590420422

  日期：——

  The synthesis and pharmacological activity of basically substituted dibenzothiazepines are described. They possess interesting antihistamine and antiserotonine activity. By varying the substituents in the benzene nuclei, and by a suitable choice the basic side chains, the specifity and activity of some derivatives could be increased considerably, especially with the dibenzothiazepinones.

  描述了基本取代的二苯并硫氮杂s的合成和药理活性。它们具有有趣的抗组胺药和抗血清素活性。通过改变在苯核的替代物，并且通过合适的选择的碱性侧链，一些衍生物的特异性和活性，可以显着地增加，特别是与dibenzothiazepinones。
• HETEROCYCLIC DERIVATIVE HAVING INHIBITORY ACTIVITY ON TYPE-I 11 DATA-HYDROXYSTEROID DEHYDROGENASE
  申请人：Itai Akiko

  公开号：US20100234363A1

  公开（公告）日：2010-09-16

  Disclosed is a compound which is useful as an 11β-hydroxysteroid dehydrogenase type 1 inhibitor. A compound represented by the formula: its pharmaceutically acceptable salt, or a solvate thereof, wherein X is O or S, a broken line and a wavy line represent the presence or the absence of a bond, (i) when a broken line represents the presence of a bond, a wavy line represents the absence of a bond, R 2 and R 3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, (ii) when a broken line represents the absence of a bond, a wavy line represents the presence of a bond, R 1 and R 4 are each independently hydrogen, halogen or the like, R 2 and R 3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, and R 5 and R 6 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like.

  本发明涉及一种化合物，可用作11β-羟基类固醇脱氢酶1型抑制剂。化合物的表示式如下：其药学上可接受的盐或其溶剂化物，其中X为O或S，一条断线和一条波浪线分别表示键的存在或不存在，(i) 当断线表示键的存在时，波浪线表示键的不存在，R2和R3各自独立地表示氢、卤素、氰基、羟基、羧基、可选取代的烷基、可选取代的烯基、可选取代的炔基或类似物，(ii) 当断线表示键的不存在时，波浪线表示键的存在，R1和R4各自独立地表示氢、卤素或类似物，R2和R3各自独立地表示氢、卤素、氰基、羟基、羧基、可选取代的烷基、可选取代的烯基、可选取代的炔基或类似物，而R5和R6各自独立地表示氢、可选取代的烷基、可选取代的烯基、可选取代的炔基或类似物。
• Tandem S_N2 Nucleophilic Substitution/Phospho-Dieckmann Reaction: One-Step Synthesis of 2-Phosphonyl-3-hydroxybenzo[<i>b</i>]thiophenes
  作者：Yuan Li、Jiamei Shen、Yawei Shen、Yanfeng Li、Kai Luo、Lei Wu

  DOI：10.1021/acs.joc.3c01526

  日期：2023.10.6

  A novel and efficient tandem SN2 nucleophilic substitution/Dieckmann condensation reaction of α-iodomethyl phosphine oxide with methyl thiosalicylate derivatives has been developed by using NaOH as a base, which enables the expeditious synthesis of 2-phosphonyl-3-hydroxybenzo[b]thiophene derivatives in moderate to high yields under simple conditions. This research provides not only a convenient method

  以NaOH为碱，开发了α-碘甲基氧化膦与硫代水杨酸甲酯衍生物的新型高效串联S N 2 亲核取代/迪克曼缩合反应，可快速合成2-膦酰基-3-羟基苯并[ b ]在简单的条件下以中等到高产率合成噻吩衍生物。该研究不仅为苯并[ b ]噻吩的2位和3位官能化提供了一种简便的方法，而且还提供了新的有机磷分子。此外，从所得的2-膦酰基-3-羟基苯并[ b ]噻吩中获得了几种新的膦酰基取代的苯并[ b ]噻吩。
• HETEROCYCLIC DERIVATIVE HAVING INHIBITORY ACTIVITY ON TYPE-I 11 -HYDROXYSTEROID DEHYDROGENASE
  申请人：Institute Of Medicinal Molecular Design, Inc.

  公开号：EP2208728A1

  公开（公告）日：2010-07-21

  Disclosed is a compound which is useful as an 11β-hydroxysteroid dehydrogenase type 1 inhibitor. A compound represented by the formula: its pharmaceutically acceptable salt, or a solvate thereof, wherein X is O or S, a broken line and a wavy line represent the presence or the absence of a bond, (i) when a broken line represents the presence of a bond, a wavy line represents the absence of a bond, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, (ii) when a broken line represents the absence of a bond, a wavy line represents the presence of a bond, R1 and R4 are each independently hydrogen, halogen or the like, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, and R5 and R6 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like.

  本发明公开了一种可用作 11β- 羟基类固醇脱氢酶 1 型抑制剂的化合物。 一种由式表示的化合物： 其药学上可接受的盐或其溶液，其中 X 是 O 或 S，折线和波浪线代表键的存在或不存在、 (i) 断线表示有键，波浪线表示无键、 R2 和 R3 各自独立地为氢、卤素、氰基、羟基、羧基、任选取代的烷基、任选取代的烯基、任选取代的炔基或类似物、 (ii) 断线表示无键，波浪线表示有键、 R1 和 R4 各自独立地为氢、卤素或类似物、 R2 和 R3 各自独立地为氢、卤素、氰基、羟基、羧基、任选取代的烷基、任选取代的烯基、任选取代的炔基或类似物，以及 R5 和 R6 各自独立地为氢、任选取代的烷基、任选取代的烯基、任选取代的炔基或类似物。