ethyl 2-sulfenamoylbenzoate | 256947-56-5

• 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: ethyl 2-sulfenamoylbenzoate
• 英文别名: Benzoic acid, 2-(aminothio)-, ethyl ester；ethyl 2-aminosulfanylbenzoate
• CAS: 256947-56-5
• 化学式: C₉H₁₁NO₂S
• 分子量: 197.258
• InChiKey: DWHWPWKPSDLMNS-UHFFFAOYSA-N

物化性质

• 沸点：
  331.2±44.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  ethyl 2-sulfenamoylbenzoate 以 甲醇 、 甲苯 为溶剂， 反应 8.0h， 生成 ethyl 2-[N-(p-methylphenyl)sulfenamoyl]benzoate
  参考文献：
  名称：

  The synthesis and reaction of N-sulfenyl heterocycles: development of effective sulfenylating reagents

  摘要：

  Various N-sulfenyl heterocycles were synthesized by transamination of sulfenamides using a chlorine gas-free method. The N-sulfenyl heterocycles behaved as sulfenylating reagents of anilines; N-sulfenylbenzimidazoles were the most effective. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.015
• 作为产物：
  描述：

  ethyl 2-mercaptobenzoate 在 hydroxylamine-O-sulfonic acid 作用下， 生成 ethyl 2-sulfenamoylbenzoate
  参考文献：
  名称：

  N-磺基吡咯的合成与反应

  摘要：

  图形摘要 摘要 N-亚磺酰吡咯是通过 N-未取代的次磺酰胺与 1,4-二羰基化合物（如己烷-2,5-二酮或 2,5-二甲氧基四氢呋喃）缩合合成的。作为亲核试剂的伯胺不会攻击 N-亚苯基吡咯中 NS 键的硫原子，这与其他 N-亚苯基杂环不同。

  DOI：

  10.1080/10426507.2015.1036991

文献信息

• Synthesis of 1,2-Benzisothiazolin-3-one by Transamination of Sulfenamides
  作者：Masao Shimizu、Ayanobu Takeda、Hidenori Fukazawa、Yoshimoto Abe、Isao Shibuya

  DOI：10.3987/com-03-9809

  日期：——

  N-Substituted sulfenamoylbenzoates were synthesized by transamination of N-unsubstituted sulfenamoylbenzoates with amines. The reaction did not always proceed by simple amine exchange between the amines and ammonia on thesulfur atom of the sulfenamides. In reactions with aliphatic amines, the sulfenamides cyclized to form N-substituted 1,2-benzisothiazolin-3-ones. The synthesis of 1,2-benzisothiazolin-3-ones

  N-取代的次磺酰基苯甲酸酯通过N-未取代的次磺酰基苯甲酸酯与胺的转氨作用合成。反应并不总是通过胺和亚磺酰胺硫原子上的氨之间的简单胺交换来进行。在与脂肪胺的反应中，亚磺酰胺环化形成 N-取代的 1,2-苯并异噻唑啉-3-酮。还通过 2-巯基苯甲酰胺的 S-胺化研究了通过分子内氨基转移合成 1,2-苯并异噻唑啉-3-酮。
• Sulfenylation of arenes and olefins with acidic sulfenamides
  作者：Masao Shimizu、Shin-ya Suzuki、Shinji Tanaka、Wataru Ando、Norio Sakai

  DOI：10.1080/10426507.2019.1603724

  日期：2019.7.3

  Abstract Sulfenylation of electron-rich arenes was carried out with N-unsubstituted sulfenamides in the presence of Brønsted or Lewis acids. α-Methylstyrene as an olefin was also sulfenylated with acidic sulfenamides, and a sulfur substituent was introduced on the methyl group. Intramolecular sulfenylation proceeded for allyl 2-sulfenamoylbenzoate derivatives, and sulfur containing seven-membered heterocycles

  摘要 在布朗斯台德酸或路易斯酸存在下，用 N-未取代的次磺酰胺对富电子芳烃进行磺酰化。作为烯烃的α-甲基苯乙烯也用酸性次磺酰胺进行了磺基化，并在甲基上引入了硫取代基。2-亚磺酰基苯甲酸烯丙酯衍生物进行分子内亚磺酰化，得到含硫的七元杂环化合物。图形概要
• 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.
• 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.
• JP2001019684A
  申请人：——

  公开号：JP2001019684A

  公开（公告）日：2001-01-23