2-methylaminobenzyl chloride | 100376-52-1

• 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: 2-methylaminobenzyl chloride
• 英文别名: 2-(chloromethyl)-N-methylaniline
• CAS: 100376-52-1
• 化学式: C₈H₁₀ClN
• 分子量: 155.627
• InChiKey: CJCKOLAXGXURKC-UHFFFAOYSA-N

物化性质

• 沸点：
  262.3±23.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methylaminobenzyl chloride 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(2-Methylamino-benzylsulfanyl)-N-pyridin-4-yl-nicotinamide
  参考文献：
  名称：

  Terauchi, Hideo; Tanitame, Akihiko; Tada, Keiko, Heterocycles, 1996, vol. 43, # 8, p. 1719 - 1734

  摘要：

  DOI：

文献信息

• A Phosphorus(III)‐Mediated (4+1)‐Cycloaddition of 1,2‐Dicarbonyls and Aza‐ <i>o</i> ‐Quinone Methides to Access 2,3‐Dihydroindoles
  作者：Kaitlyn E. Eckert、Antonio J. Lepore、Brandon L. Ashfeld

  DOI：10.1002/hlca.201900192

  日期：2019.12

  A (4+1)‐cycloaddition is reported between 1,2‐dicarbonyls and aza‐o‐quinone methide precursors to access 2,3‐dihydroindoles bearing a tetra‐substituted carbon center. The utilization of dioxyphospholenes as carbene surrogates provided dihydroindoles in 20–90 % yield, wherein the electronic nature of the dioxyphospholene impacts its role in the reaction.

  据报道，在1,2-二羰基化合物和氮杂-邻-醌甲基化物前体之间存在（4 + 1）-环加成反应，以进入带有一个四取代碳中心的2,3-二氢吲哚。利用二氧膦作为卡宾替代物可以提供20-90％的二氢吲哚，其中二氧膦的电子性质会影响其在反应中的作用。
• Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase
  作者：Gilbert W. Adelstein、Chung H. Yen、Richard A. Haack、Stella Yu、Gary Gullikson、Doreen V. Price、Charles Anglin、Dennis L. Decktor、Henry Tsai、Robert H. Keith

  DOI：10.1021/jm00401a024

  日期：1988.6

  A series of substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines were synthesized as potential inhibitors of the acid secretory enzyme H+/K+ ATPase. Substitutions on the aniline nitrogen atom resulted in potent enzyme inhibition in vitro but weak activity in gastric fistula dogs. Electron-donating substituents on the aniline ring enhanced in vitro and in vivo potency relative to the unsubstituted analogue. The potency showed a correlation to the calculated pKa of the aniline nitrogen atom. Substitutions on the aniline and benzimidazole rings did not further enhance potency. Di- and trisubstituted aniline derivatives were potent inhibitors of the enzyme system. The preferred combination of substituents were a methoxy group on the benzimidazole ring and a single alkyl group on the aniline ring. One such compound, 76, was an effective inhibitor of acid secretion in the dog and was selected for further pharmacological study.
• US4933458A
  申请人：——

  公开号：US4933458A

  公开（公告）日：1990-06-12
• US5106976A
  申请人：——

  公开号：US5106976A

  公开（公告）日：1992-04-21