ethenesulfinyl chloride | 216007-76-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: ethenesulfinyl chloride
• CAS: 216007-76-0
• 化学式: C₂H₃ClOS
• 分子量: 110.564
• InChiKey: WEMOSJQAKDQWJW-UHFFFAOYSA-N

物化性质

• 沸点：
  177.4±23.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 ethenesulfinyl chloride 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以59%的产率得到ethenesulfinylmethyl phenyl ketone
  参考文献：
  名称：

  1-Alkenesulfinyl Chlorides:  Synthesis, Characterization, and Some Substitution Reactions

  摘要：

  A number of 1-alkenyl sulfoxides bearing either a diphenylmethyl (DPM) or a p-methoxybenzyl (PMB) group have been prepared and exposed to the chlorine surrogate SO2Cl2. Through an oxidative fragmentation reaction, a new family of sulfur acid derivatives, 1-alkenesulfinyl chlorides, is generated. They can be characterized by IR spectroscopy before chemical capture with an alcohol. Ethenesulfinyl chloride (2a) and 1-propenesulfinyl chloride (2b), obtained from their corresponding DPM precursor, can be distilled at reduced pressure to afford ca. 90% pure material. NMR chemical shift comparison of various 1-alkenesulfinyl-containing compounds is made. 1-Alkenesulfinylmethyl phenyl(alkyl) ketones (6) can be prepared directly from sulfinyl chlorides 2 although decomposition and/or isomerization is sometimes extensive during purification.

  DOI：

  10.1021/jo980970t
• 作为产物：
  描述：

  1-Ethenesulfinylmethyl-4-methoxy-benzene 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 ethenesulfinyl chloride
  参考文献：
  名称：

  1-Alkenesulfinyl Chlorides:  Synthesis, Characterization, and Some Substitution Reactions

  摘要：

  A number of 1-alkenyl sulfoxides bearing either a diphenylmethyl (DPM) or a p-methoxybenzyl (PMB) group have been prepared and exposed to the chlorine surrogate SO2Cl2. Through an oxidative fragmentation reaction, a new family of sulfur acid derivatives, 1-alkenesulfinyl chlorides, is generated. They can be characterized by IR spectroscopy before chemical capture with an alcohol. Ethenesulfinyl chloride (2a) and 1-propenesulfinyl chloride (2b), obtained from their corresponding DPM precursor, can be distilled at reduced pressure to afford ca. 90% pure material. NMR chemical shift comparison of various 1-alkenesulfinyl-containing compounds is made. 1-Alkenesulfinylmethyl phenyl(alkyl) ketones (6) can be prepared directly from sulfinyl chlorides 2 although decomposition and/or isomerization is sometimes extensive during purification.

  DOI：

  10.1021/jo980970t

文献信息

• Synthesis and characterization of homochiral cholesteryl 1-alkenesulfinate esters
  作者：Rick R. Strickler、Adrian L. Schwan

  DOI：10.1016/s0957-4166(00)00474-2

  日期：2000.12

  A number of alpha,beta -unsaturated sulfinyl chlorides 1 has been separately prepared and treated with (-)-cholesterol under various conditions some of which incorporated chiral amines quinine or quinidine. Some (R-S) vinylic sulfinates could be isolated in enantiopure form following one or two recrystallizations of the resulting diastereomeric mixtures of (-)-cholesteryl 1-alkenesulfinates 2. Access to diastereomerically enriched (S-S) vinylic sulfinates (66-75% de) was achieved in three instances. Absolute stereochemical assignments were made with the assistance of the chiral solvating agent (R)-2,2,2-trifluoro-1-(9-anthryl)ethanol. (C) 2001 Elsevier Science Ltd, All rights reserved.
• Highly Diastereoselective Intramolecular Diels−Alder Reactions of Furan-Tethered 1-Alkenesulfinic Acid Esters
  作者：Adrian L. Schwan、Jennifer L. Snelgrove、Mark L. Kalin、Robert D. J. Froese、Keiji Morokuma

  DOI：10.1021/ol990674i

  日期：1999.8.1

  [GRAPHICS]The capture of selected 1-alkenesulfinyl chlorides with furan-tethered alcohols leads to the formation of diene-tethered 1-alkenesulfinate esters, The esters can spontaneously or with Lewis acid treatment undergo an IM DA reaction to form exo adducts with very high diastereoselectivity. Computational predictions using density functional theory indicate the preferred transition state for cyclization and find little preference for the sulfinyl configuration in the products.
• 1-Alkenesulfinyl Chlorides:  Synthesis, Characterization, and Some Substitution Reactions
  作者：Adrian L. Schwan、Rick R. Strickler、Yvonne Lear、Mark L. Kalin、Tanya E. Rietveld、Ting-Jian Xiang、Denis Brillon

  DOI：10.1021/jo980970t

  日期：1998.10.1

  A number of 1-alkenyl sulfoxides bearing either a diphenylmethyl (DPM) or a p-methoxybenzyl (PMB) group have been prepared and exposed to the chlorine surrogate SO2Cl2. Through an oxidative fragmentation reaction, a new family of sulfur acid derivatives, 1-alkenesulfinyl chlorides, is generated. They can be characterized by IR spectroscopy before chemical capture with an alcohol. Ethenesulfinyl chloride (2a) and 1-propenesulfinyl chloride (2b), obtained from their corresponding DPM precursor, can be distilled at reduced pressure to afford ca. 90% pure material. NMR chemical shift comparison of various 1-alkenesulfinyl-containing compounds is made. 1-Alkenesulfinylmethyl phenyl(alkyl) ketones (6) can be prepared directly from sulfinyl chlorides 2 although decomposition and/or isomerization is sometimes extensive during purification.