diphenylmethyl (E)-(3,3-dimethyl-1-butenyl) sulfoxide | 216007-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diphenylmethyl (E)-(3,3-dimethyl-1-butenyl) sulfoxide
• 英文别名: [[(E)-3,3-dimethylbut-1-enyl]sulfinyl-phenylmethyl]benzene
• CAS: 216007-62-4
• 化学式: C₁₉H₂₂OS
• 分子量: 298.449
• InChiKey: QCNBXPUOKAZQDT-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  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
• 作为产物：
  描述：

  二苯基溴甲烷 、 (1R,2R)-2-tert-Butyl-thiirane 1-oxide 在 lithium hexamethyldisilazane 作用下， 生成 diphenylmethyl (E)-(3,3-dimethyl-1-butenyl) sulfoxide
  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

• 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.
• 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.