diphenylmethyl ethenyl sulfoxide | 176907-85-0

• 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 ethenyl sulfoxide
• 英文别名: [Ethenylsulfinyl(phenyl)methyl]benzene
• CAS: 176907-85-0
• 化学式: C₁₅H₁₄OS
• 分子量: 242.342
• InChiKey: DHLYVIZFOFEZLK-UHFFFAOYSA-N

物化性质

• 沸点：
  433.8±45.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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 ethenyl sulfoxide 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：

  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
• 作为产物：
  描述：

  thiirane 1-oxide 、 二苯基溴甲烷 在 lithium hexamethyldisilazane 作用下， 生成 diphenylmethyl ethenyl 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

• Oxidative fragmentations of selected 1-alkenyl sulfoxides. Chemical and spectroscopic evidence for 1-alkenesulfinyl chlorides
  作者：Adrian L. Schwan、Mark L. Kalin、Kristin E. Vajda、Ting-Jian Xiang、Denis Brillon

  DOI：10.1016/0040-4039(96)00281-x

  日期：1996.4

  A collection of 1-alkenyl sulfoxides possessing diphenylmethyl, p-methoxybenzyl or 2-(trimethylsilyl)ethyl groups can be converted to 1-alkenesulfinyl chlorides using SO2Cl2. The 1-alkenesulfinyl chlorides were spectroscopically characterized by IR and were chemically captured as their cyclohexyl or 3-phenylpropyl 1-alkenesulfinate esters. Copyright (C) 1996 Elsevier Science Ltd
• 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.
• 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.