N-(2-methoxycarbonylbenzenesulfenyl)benzimidazole | 658702-70-6

• 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: N-(2-methoxycarbonylbenzenesulfenyl)benzimidazole
• 英文别名: Methyl 2-(benzimidazol-1-ylsulfanyl)benzoate
• CAS: 658702-70-6
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: ARGRKMILAJOKBV-UHFFFAOYSA-N

物化性质

• 熔点：
  167-169 °C
• 沸点：
  470.0±47.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-methoxycarbonylbenzenesulfenyl)benzimidazole 、 甲基乙酰亚胺酯盐酸盐 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到methyl N-(2-methoxycarbonylsulfenyl)acetimidate
  参考文献：
  名称：

  N-(2-Alkoxycarbonylbenzenesulfenyl)benzimidazoles as Nitrogen-, Sulfur-, and Carbon-Sulfenylation Reagents

  摘要：

  N-(2-Alkoxycarbonylbenzenesulfenyl)benzimidazoles reacted with nucleophiles such as amides, imidates, thiols, Grignard reagents, and active methylene compounds to yield the corresponding sulfenylated products: N-acylsulfenamides, N-sulfenylimidates, disulfides, sulfides, and sulfenylated active methylene compounds, respectively.

  DOI：

  10.3987/com-06-10904
• 作为产物：
  描述：

  苯并咪唑 、 2-(氨基硫代)苯甲酸甲酯 以 甲苯 为溶剂， 反应 10.0h， 以78%的产率得到N-(2-methoxycarbonylbenzenesulfenyl)benzimidazole
  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

文献信息

• Unsymmetrical Cysteine Disulfides as Carbonic Anhydrase Inhibitors
  作者：N. Stellenboom、R. Hunter、M. Caira、A. Oztekin、K. Zilbeyaz

  DOI：10.1134/s1068162021050344

  日期：2021.9

  Abstract A small library of unsymmetrical cysteine disulfides as four aliphatic, three aromatic and one heteroaromatic were evaluated for their inhibition of two important carbonic anhydrase (CA) enzymes, namely human carbonic anhydrase isoenzymes I (hCA I) and II (hCA II). IC50 values were recorded in the low nanomolar range (8.6–18.3 nM for hCA I and 42.9–99.9 nM for hCA II). The inhibition activities

  摘要 评估了作为四种脂肪族、三种芳香族和一种杂芳香族的不对称半胱氨酸二硫化物的小型文库对两种重要碳酸酐酶 (CA) 的抑制作用，即人类碳酸酐酶同工酶 I (hCA I) 和 II (hCA II)。IC 50值记录在低纳摩尔范围内（hCA I 为 8.6-18.3 nM，hCA II 为 42.9-99.9 nM）。抑制活性显着优于临床可用的 CA 抑制剂乙酰唑胺对 hCA I 的抑制活性，而对 hCA II 仅稍差。这些结果强调了筛选小分子作为潜在 CA 抑制剂 (CAIs) 的相关性。
• N-(2-Alkoxycarbonylbenzenesulfenyl)benzimidazoles as Nitrogen-, Sulfur-, and Carbon-Sulfenylation Reagents
  作者：Masao Shimizu、Hidenori Fukazawa、Junﾕichi Inoue、Yoshimoto Abe、Takeo Konakahara

  DOI：10.3987/com-06-10904

  日期：——

  N-(2-Alkoxycarbonylbenzenesulfenyl)benzimidazoles reacted with nucleophiles such as amides, imidates, thiols, Grignard reagents, and active methylene compounds to yield the corresponding sulfenylated products: N-acylsulfenamides, N-sulfenylimidates, disulfides, sulfides, and sulfenylated active methylene compounds, respectively.
• The synthesis and reaction of N-sulfenyl heterocycles: development of effective sulfenylating reagents
  作者：Masao Shimizu、Hidenori Fukazawa、Shigeru Shimada、Yoshimoto Abe

  DOI：10.1016/j.tet.2005.12.015

  日期：2006.3

  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.