(Z)-2-carbomethoxyethenesulfinyl chloride | 216007-84-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-2-carbomethoxyethenesulfinyl chloride
• 英文别名: methyl (Z)-3-chlorosulfinylprop-2-enoate
• CAS: 216007-84-0
• 化学式: C₄H₅ClO₃S
• 分子量: 168.601
• InChiKey: FCJWVHDLTZSYGE-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-carbomethoxyethenesulfinyl chloride 、 环己醇 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-3-Cyclohexyloxysulfinyl-acrylic acid methyl ester
  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：

  p-methoxybenzyl (Z)-carbomethoxyethenyl sulfoxide 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-2-carbomethoxyethenesulfinyl chloride
  参考文献：
  名称：

  Highly Diastereoselective Intramolecular Diels−Alder Reactions of Furan-Tethered 1-Alkenesulfinic Acid Esters

  摘要：

  [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.

  DOI：

  10.1021/ol990674i