methyl 5-chloro-2-sulfenamoylbenzoate | 256947-58-7

• 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: methyl 5-chloro-2-sulfenamoylbenzoate
• 英文别名: Methyl 2-aminosulfanyl-5-chlorobenzoate
• CAS: 256947-58-7
• 化学式: C₈H₈ClNO₂S
• 分子量: 217.676
• InChiKey: XAPWSDQGIWRURN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-chloro-2-sulfenamoylbenzoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以75%的产率得到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-chloro-2-mercapto-benzoic acid methyl ester 在 氢氧化钾 、 hydroxylamine-O-sulfonic acid 作用下， 以 水 为溶剂， 反应 0.5h， 以70%的产率得到methyl 5-chloro-2-sulfenamoylbenzoate
  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

文献信息

• Sythesis of 2-(2-Alkoxycarbonylphenylthio)-1,2-benzisothiazolin-3-ones from 2-Sulfenamoylbenzoates
  作者：Masao Shimizu、Toshiyuki Takagi、Motonari Shibakami、Yasuo Gama、Isao Shibuya

  DOI：10.3987/com-00-9046

  日期：——

  The mechanism of formation of 2-(2-alkoxycarbonylphenyl-thio)-1,2-benzisothiazolin-3-ones, which were obtained by the heating of 2-sulfenamoylbenzoates, was investigated. It appears that transamination occurred on the sulfur atom of a 2-sulfenamoylbenzoate between the amino group and the 1,2-benzisothiazolin-3-one, which formed by the cyclization of methyl 2-sulfenamoylbenzoate after heating, to give 2-(2-methoxycarbonylphenylthio)-1,2-benzisothiazolin-3-ones. Several types of 2-sulfenyl-1,2-benzisothiazolin-3-ones were synthesized from the 2-sulfenamoylbenzoates.
• A Facile Synthesis of 1,2-Benzisothiazolin-3-ones from Thiosalicylates
  作者：Masao Shimizu、Hisashi Kikumoto、Takeo Konakahara、Yasuo Gama、Isao Shibuya

  DOI：10.3987/com-99-8706

  日期：——

  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.