<1,1-(2)H2>-<(2-Chloroethyl)thio>benzene | 151388-56-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: <1,1-(2)H2>-<(2-Chloroethyl)thio>benzene
• 英文别名: 2-(Phenylthio)ethyl-2,2-d2 chloride；(2-Chloro-1,1-dideuterioethyl)sulfanylbenzene
• CAS: 151388-56-6
• 化学式: C₈H₉ClS
• 分子量: 174.663
• InChiKey: QDXIHHOPZFCEAP-RJSZUWSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  <1,1-(2)H2>-<(2-Chloroethyl)thio>benzene 以40%的产率得到
  参考文献：
  名称：

  McManus Samuel P., Karaman Rashid M., Sedaghat-Herati Reza, Hovanes Bruce+, J. Org. Chem, 58 (1993) N 23, S 6466-6469

  摘要：

  DOI：
• 作为产物：
  描述：

  [1,1-(2)H2]-2-氯乙醇 、 二苯二硫醚 在 吡啶 、 三丁基膦 作用下， 反应 12.0h， 以49%的产率得到<1,1-(2)H2>-<(2-Chloroethyl)thio>benzene
  参考文献：
  名称：

  Preparation of 2-chloroethyl-1,1-d2 phenyl sulfide without appreciable scrambling

  摘要：

  DOI：

  10.1021/jo00075a051

文献信息

• Shamrock surfactants and their methods of use
  申请人：Jaeger A. David

  公开号：US20070185006A1

  公开（公告）日：2007-08-09

  Disclosed are surfactants that contain two ionic or polar nonionic head groups, each connected to a central ionic head group by a hydrocarbon linking moiety. The central head group is a dithiophosphate, dithiocarbamate, or quaternary ammonium group. These surfactants have potential applications in chemical decontamination of mustard (simulants), storage and release devices/chemical switches and the remediation of heavy-metal ion-contaminated water.

  本发明涉及一种表面活性剂，其包含两个离子性或极性非离子性头基，每个头基通过一个烃链连接基团连接到一个中心离子性头基。中心头基是二硫代磷酸盐、二硫代氨基甲酸盐或季铵基团。这些表面活性剂在芥末（模拟物）化学去污、储存和释放装置/化学开关以及重金属离子污染水的修复方面具有潜在应用。
• Reaction of Halide Ion with 2-(Phenylthio)ethyl Halides in Acetone
  作者：Samuel P. McManus、Rashid M. Karaman、Reza Sedaghat-Herati、J. Milton Harris

  DOI：10.1021/jo00120a019

  日期：1995.7

  2-(Phenylthio)ethyl chloride specifically deuterated alpha to the sulfur atom (i.e. 2-Cl) was employed to study the mechanism of displacement of chloride ion by iodide ion in dry acetone solution. Experimental evidence including rate studies has been accumulated that allows the conclusion to be drawn that iodide ion displaces chloride ion from 2-Cl by a classical S(N)2 mechanism to give 2-I. Under the reaction conditions, however, 2-I is reactive toward anchimerically-assisted ionization which leads to product with the deuterium label scrambled. Reaction of 2-Cl with bromide ion follows a similar course. Our displacement reactions of halide ions by halide ions showed the expected nucleophilicity order of Cl- > Br- > I- and the normal leaving group order of I- > Br- > Cl-. An interesting counterion effect was noted with iodides displacing chloride ion. While potassium iodide in acetone converted 2-Cl to the mixture of iodides 2-I and 3-I, tetrabutylammonium iodide caused conversion but the products reverted completely back to the label-scrambled chlorides. The difference in these results is probably because of differences in the thermodynamics of the two systems.
• McManus Samuel P., Karaman Rashid M., Sedaghat-Herati Reza, Hovanes Bruce+, J. Org. Chem, 58 (1993) N 23, S 6466-6469
  作者：McManus Samuel P., Karaman Rashid M., Sedaghat-Herati Reza, Hovanes Bruce+

  DOI：——

  日期：——
• Synthesis, isolation, and reactivity of a deuterated mustard simulant: 2-(phenylthio)ethyl-2,2-d2 chloride
  作者：Samuel P. McManus、Rashid M. Karaman、Reza Sedaghat-Herati、Bruce A. Hovanes、Xin Teng Ding、J. Milton Harris

  DOI：10.1021/jo00075a050

  日期：1993.11

  We have achieved the synthesis and isolation, without substantial label scrambling, of 2-(phenylthio)-ethyl-2,2-d2 chloride (2-Cl), a compound useful in modeling reactions of mustard and other highly reactive beta-thioethyl chlorides. 2-Cl undergoes slow label scrambling upon dissolution in hot, dry acetonitrile or acetone. Rates of scrambling of the deuterium label in 2-Cl have been measured by following proton NMR changes. Our present work clearly demonstrates that cyclic sulfonium ions are involved in these scrambling reactions. In anhydrous or aqueous acetone, thiourea traps the sulfonium ion intermediate to give stable, label-scrambled thiouronium salts. In anhydrous acetone, in competition with formation of the thiouronium salts, chloride return occurs giving 2-Cl and its label-scrambled isomer, 2-(phenylthio)ethyl-1,1-d2 Chloride (1-Cl). However, no chloride return is observed in 60% aqueous acetone. Mechanistic implications of these results are presented.
• DEUTERIUM-ENRICHED ELETRIPTAN
  申请人：Czarnik Anthony W.

  公开号：US20090062367A1

  公开（公告）日：2009-03-05

  The present application describes deuterium-enriched eletriptan, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.