1-amino-2-chloro-4-<(1,1-dimethylethyl)thio>benzene | 75794-24-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-amino-2-chloro-4-<(1,1-dimethylethyl)thio>benzene
• 英文别名: 2-chloro-4-t-butylthioaniline；2-chloro-4-tert-butylthioaniline；4-tert-butylsulfanyl-2-chloroaniline
• CAS: 75794-24-0
• 化学式: C₁₀H₁₄ClNS
• 分子量: 215.747
• InChiKey: IOAJLDYIVHJCKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴代叔丁烷 、 N,N-二甲基环己胺 、 2-氯-4-巯基苯胺 以 二氯甲烷 为溶剂， 生成 1-amino-2-chloro-4-<(1,1-dimethylethyl)thio>benzene
  参考文献：
  名称：

  Substituted-4-alkylthioalkane-sulfonanilides and operatives

  摘要：

  直链烷烃和单卤代烷烃磺胺苯酰胺在对位被烷基硫、烷基亚砜和烷基砜基取代，并且额外被卤素取代，也可以选择性地被三氟甲基取代，并且其农业上可接受的盐是有用的除草剂。

  公开号：

  US04913728A1

文献信息

• Influence of ion pairing, steric effects, and other specific interactions on the reactivity of thioanions with chloronitrobenzenes. Nucleophilic aromatic substitution vs. reduction
  作者：Stefano Montanari、Cristina Paradisi、Gianfranco Scorrano

  DOI：10.1021/jo00013a037

  日期：1991.6

  The reactions in 2-propanol of the isomeric chloronitrobenzenes with thiolate nucleophiles, RS- (R = Me, i-Pr, t-Bu, Ph), have been studied to test for the ability of these representative thioanions of inducing chloride displacement and/or nitro reduction. m-Chloronitrobenzene gives a complex mixture of products, all still retaining the chlorine substituent, via redox processes involving nitro reduction and ring alkylthiolation. In contrast, the ortho and para isomers undergo substitution of chloride according to the addition/elimination S(N)Ar mechanism also when O2 is removed from the reaction environment. Notably, treatment of o- and p-chloronitrobenzene with the oxanion 2-propoxide in oxygen-free i-PrOH results, instead, in nitro reduction. Kinetic and product studies indicate that i-PrS- is more reactive than i-PrO- in both redox and S(N)Ar reactions, the difference in reactivity being, however, considerably greater in the latter process. The MeS- > i-PrS- > PhS- > t-BuS- reactivity order observed in the S(N)Ar reactions is opposite, as far as the aliphatic thiolates are concerned, to the order of basicity. Notably, reactivity drops with increasing bulkiness of the attacking nucleophile. However, kinetic results obtained under conditions of ion paired and of ''free'' anions and the effects of ion pairing on the k(ortho)/k(para) ratios suggest that steric effects in the transition states are scarcely dependent on the bulkiness of the substituent R in the nucleophile RS- and that nucleophilic reactivity is largely determined by the extent of charge concentration on the attacking atom, which, in turn, affects the strength of ion-pairing interactions.
• US4913728A
  申请人：——

  公开号：US4913728A

  公开（公告）日：1990-04-03