(E)-t-butylethenesulfinyl chloride | 216007-79-3

• 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: (E)-t-butylethenesulfinyl chloride
• 英文别名: (E)-3,3-dimethylbut-1-ene-1-sulfinyl chloride
• CAS: 216007-79-3
• 化学式: C₆H₁₁ClOS
• 分子量: 166.672
• InChiKey: VXTLJMCORHYSEF-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (E)-t-butylethenesulfinyl chloride 在 胆固醇 、 奎尼丁 、 奎宁 作用下， 以 二氯甲烷 为溶剂， 生成 [R_S]-(E)-3,3-dimethyl-1-butenyl cyclohexyl sulfoxide
  参考文献：
  名称：

  Andersen chemistry with an α,β-unsaturated sulfinyl chloride: synthesis and Grignard reactions of homochiral cholesteryl (R)S-(E)-t-butylethenesulfinate

  摘要：

  (-)-胆固醇基 (R)(S)-(E)-叔丁基乙烯基磺酸酯 2 通过 (E)-叔丁基乙烯基磺酰氯与 (-)-胆固醇在金鸡纳碱的存在下反应制得，以光学纯形式获得（收率约 36%）。(S)-2 的立体异构体富集版本通过提高 d.e.s 至 75% 制备。2 的 Grignard 取代反应以高度的立体专一性进行，以良好的收率和优异的 e.e. 提供了新的途径，用于获得光学 enriched 的 (E)-2-叔丁基乙烯基芳基硫醚磺酰化物。© 1999 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0957-4166(99)00439-5
• 作为产物：
  描述：

  diphenylmethyl (E)-(3,3-dimethyl-1-butenyl) sulfoxide 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-t-butylethenesulfinyl 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.
• 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.
• Andersen chemistry with an α,β-unsaturated sulfinyl chloride: synthesis and Grignard reactions of homochiral cholesteryl (R)S-(E)-t-butylethenesulfinate
  作者：Rick R Strickler、Adrian L Schwan

  DOI：10.1016/s0957-4166(99)00439-5

  日期：1999.10

  (-)-Cholesteryl (R)(s)-(E)-t-butylethenesulfinate 2 was prepared in enantiopure form through the reaction of (E)t-butylethenesulfinyl chloride and (-)-cholesterol in the presence of quinine (ca. 36% yield). Diastereomerically enriched versions of (S)-2 were prepared with d.e.s up to 75%. Grignard substitution reactions of 2 proceed with high stereospecificity to provide a new access to enantiomerically enriched (E)-2-t-butylethenylaralkyl sulfoxides in good yield and excellent e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (-)-胆固醇基 (R)(S)-(E)-叔丁基乙烯基磺酸酯 2 通过 (E)-叔丁基乙烯基磺酰氯与 (-)-胆固醇在金鸡纳碱的存在下反应制得，以光学纯形式获得（收率约 36%）。(S)-2 的立体异构体富集版本通过提高 d.e.s 至 75% 制备。2 的 Grignard 取代反应以高度的立体专一性进行，以良好的收率和优异的 e.e. 提供了新的途径，用于获得光学 enriched 的 (E)-2-叔丁基乙烯基芳基硫醚磺酰化物。© 1999 Elsevier Science Ltd. 保留所有权利。