phenyl 2,2-dideutero-2-hydroxyethyl sulfide | 177416-12-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 2,2-dideutero-2-hydroxyethyl sulfide
• 英文别名: 1,1-dideuterio-2-phenylsulfanylethanol
• CAS: 177416-12-5
• 化学式: C₈H₁₀OS
• 分子量: 156.217
• InChiKey: KWWZHCSQVRVQGF-NCYHJHSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,2-dideutero-2-hydroxyethyl sulfide 在 氢氧化钾 、 铜 、 邻苯三酚 作用下， 生成 2,2-dideuterioethenylsulfanylbenzene
  参考文献：
  名称：

  Electrophilic substitution at an olefinic carbon atom. Some studies of the mechanism of the trifluoroacetylation of aryl vinyl sulfides

  摘要：

  A study of the mechanism of the trifluoroacetylation of aryl vinyl sulfides was made. The rates of trifluoroacetylation of ArSCH = CH2, ArSCH = CD2, cis-ArSCH = CHD, and trans-ArSCH = CHD were determined. The results imply that this electrophilic substitution reaction proceeds by a single-step mechanism.

  DOI：

  10.1021/jo00006a001
• 作为产物：
  描述：

  2-(苯硫基)乙醛 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到phenyl 2,2-dideutero-2-hydroxyethyl sulfide
  参考文献：
  名称：

  通过Me 3 SiI促进硫化物分子内置换氢氧化物或甲醇，形成环sulf盐。环收缩硫烷→硫烷

  摘要：

  适当定位的（1、2、1、1、4和1、5-）分子内硫化物会干扰碘代三甲基硅烷促进的碘的羟基取代，以及相关的醇脱保护步骤（甲基醚的区域选择性裂解）。结果可能是由于intermediate中间体的裂解而产生的环状an盐或碘化物。特别优选仲和叔醇或醚以及脂族而不是芳族硫化物官能团的环化。该反应的跨环形形式导致7元至5元环状硫化物的容易的环收缩。

  DOI：

  10.1016/0040-4020(96)00229-3

文献信息

• Role of neighboring group participation in the acetolysis of .alpha.-(phenylthio)-.omega.-[(p-tolylsulfonyl)oxy]alkanes
  作者：Vittorio Rosnati、Antonio Saba、Antonella Angius、Daniele Casarini

  DOI：10.1021/jo00227a027

  日期：1987.9
• HOJO, MASARU;MASUDA, RYOICHI;KAMITORI, YASUHIRO;OKADA, ETSUJI, J. ORG. CHEM., 56,(1991) N, C. 1975-1976
  作者：HOJO, MASARU、MASUDA, RYOICHI、KAMITORI, YASUHIRO、OKADA, ETSUJI

  DOI：——

  日期：——
• 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：——
• SEDAGHAT-HERATI, M. R.;MCMANUS, SAMUEL P.;HARRIS, J. MILTON, J. ORG. CHEM., 53,(1988) N 11, C. 2539-2543
  作者：SEDAGHAT-HERATI, M. R.、MCMANUS, SAMUEL P.、HARRIS, J. MILTON

  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.