4-amino-2-chloro-1-<(1-methylethyl)thio>benzene | 5211-09-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-amino-2-chloro-1-<(1-methylethyl)thio>benzene
• 英文别名: 3-Chloro-4-isopropylthioanilin；4-Isopropylthio-3-chloranilin；3-Chloro-4-propan-2-ylsulfanylaniline
• CAS: 5211-09-6
• 化学式: C₉H₁₂ClNS
• 分子量: 201.72
• InChiKey: YRAVCIDRZGHVSI-UHFFFAOYSA-N

物化性质

• 熔点：
  42.5-43.5 °C
• 沸点：
  316.3±27.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-amino-2-chloro-1-<(1-methylethyl)thio>benzene 、 巴豆酰氯 在 三乙胺 作用下， 以 苯 为溶剂， 生成 But-3-enoic acid (3-chloro-4-isopropylsulfanyl-phenyl)-amide
  参考文献：
  名称：

  GB1141183

  摘要：

  公开号：
• 作为产物：
  描述：

  2-丙烷硫醇钠 、 3,3'-二氯氧化偶氮苯 以 异丙醇 为溶剂， 反应 1.0h， 以51%的产率得到3-氯苯胺
  参考文献：
  名称：

  A new reaction of the azoxy group with alkyl thiolates: Reduction to amino via a sulfenamido intermediate

  摘要：

  A novel alkyl thiolate-induced reduction of azoxybenzenes is reported to yield anilines via in situ decomposition of the corresponding sulfenamides formed as primary reaction products.

  DOI：

  10.1016/s0040-4039(00)76537-3

文献信息

• Model studies on a synthetically facile series of N-substituted phenyl-N′-pyridin-3-yl ureas leading to 1-(3-pyridylcarbamoyl) indolines that are potent and selective 5-HT2C/2B receptor antagonists
  作者：Steven M. Bromidge、Steven Dabbs、David T. Davies、Susannah Davies、D.Malcolm Duckworth、Ian T. Forbes、Angela Gadre、Peter Ham、Graham E. Jones、Frank D. King、Damian V. Saunders、Kevin M. Thewlis、Deepa Vyas、Thomas P. Blackburn、Vicky Holland、Guy A. Kennett、Graham J. Riley、Martyn D. Wood

  DOI：10.1016/s0968-0896(99)00228-x

  日期：1999.12

  antagonists have been prepared by rapid parallel synthesis. These N-substituted phenyl-N'-pyridin-3-yl ureas were found to have a range of 5-HT2C receptor affinities and selectivities over the closely related 5-HT2A receptor. Extrapolation of simple SAR, derived from this set of compounds, to the more active but synthetically more complex 1-(3-pyridylcarbamoyl)indoline series allowed us to target optimal

  已经通过快速平行合成制备了一系列的5-HT 2C拮抗剂模型。发现这些N-取代的苯基-N'-吡啶-3-基脲比密切相关的5-HT2A受体具有一系列的5-HT2C受体亲和力和选择性。从这组化合物中衍生出的简单SAR外推至活性更高但合成上更复杂的1-（3-吡啶基氨基甲酰基）二氢吲哚系列，使我们能够靶向最佳取代模式并鉴定有效和选择性的5-HT（2C / 2B）拮抗剂。
• 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.
• INDOLINE DERIVATIVES AS 5HT2C ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0707581B1

  公开（公告）日：1997-02-26
• US5834494A
  申请人：——

  公开号：US5834494A

  公开（公告）日：1998-11-10
• GB1141183
  申请人：——

  公开号：——

  公开（公告）日：——