(Z)-1-phenylsulfinyl-2-phenylsulfanylethylene | 848412-25-9

• 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: (Z)-1-phenylsulfinyl-2-phenylsulfanylethylene
• 英文别名: [(Z)-2-(benzenesulfinyl)ethenyl]sulfanylbenzene
• CAS: 848412-25-9
• 化学式: C₁₄H₁₂OS₂
• 分子量: 260.381
• InChiKey: CQTDCUJMMRBNJO-QXMHVHEDSA-N

物化性质

• 沸点：
  453.3±37.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1-phenylsulfinyl-2-phenylsulfanylethylene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到cis-1,2-bis-phenylsulfanyl-ethylene
  参考文献：
  名称：

  Reactivity of 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE) with O-nucleophiles generated by potassium tert-butoxide

  摘要：

  E-1-Phenylsulfinyl-2-phenylsulfanylethylene (E-SOSE) reacts with O-nucleophiles generated by means of t-BuOK via an addition-elimination mechanism, thus affording the product of substitution of the phenylsulfanyl group in a stereo-conservative process. When used alone, the strongly basic and hindered tert-butoxide brings about elimination of either the phenylthiolate or phenylsulfinate groups. Z-SOSE is much more prone to elimination: either with t-BuOK alone or with other O-nucleophiles generated by t-BuOK, it always leads to products derived from elimination. Other alkaline tert-butoxides or other bases appear not as effective in generating species nucleophilic enough to react with E-SOSE. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.125
• 作为产物：
  描述：

  cis-1,2-bis-phenylsulfanyl-ethylene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-1-phenylsulfinyl-2-phenylsulfanylethylene
  参考文献：
  名称：

  Expeditious synthesis of β-cycloacetalic sulfoxides. Introducing 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE), a promising new alkenylsulfur reagent

  摘要：

  In similarity with the strongly electrophilic BPSEs and despite its more electron-rich character, 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE) reacts with nucleophiles with displacement of the phenylthio moiety. Specifically it reacts with diols under basic conditions to produce beta-cycloacetalic sulfoxides. The reaction has been amply developed in carbohydrate chemistry. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.151

文献信息

• Expeditious synthesis of β-cycloacetalic sulfoxides. Introducing 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE), a promising new alkenylsulfur reagent
  作者：Elena Cabianca、Arnaud Tatibouët、Fabrizio Fabris、Ottorino De Lucchi、Patrick Rollin

  DOI：10.1016/j.tetlet.2004.11.151

  日期：2005.2

  In similarity with the strongly electrophilic BPSEs and despite its more electron-rich character, 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE) reacts with nucleophiles with displacement of the phenylthio moiety. Specifically it reacts with diols under basic conditions to produce beta-cycloacetalic sulfoxides. The reaction has been amply developed in carbohydrate chemistry. (C) 2004 Elsevier Ltd. All rights reserved.
• Reactivity of 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE) with O-nucleophiles generated by potassium tert-butoxide
  作者：Leonardo Pellizzaro、Elena Cabianca、Arnaud Tatibouët、Pierluigi Padovan、Fabrizio Fabris、Patrick Rollin、Ottorino De Lucchi

  DOI：10.1016/j.tetlet.2007.03.125

  日期：2007.5

  E-1-Phenylsulfinyl-2-phenylsulfanylethylene (E-SOSE) reacts with O-nucleophiles generated by means of t-BuOK via an addition-elimination mechanism, thus affording the product of substitution of the phenylsulfanyl group in a stereo-conservative process. When used alone, the strongly basic and hindered tert-butoxide brings about elimination of either the phenylthiolate or phenylsulfinate groups. Z-SOSE is much more prone to elimination: either with t-BuOK alone or with other O-nucleophiles generated by t-BuOK, it always leads to products derived from elimination. Other alkaline tert-butoxides or other bases appear not as effective in generating species nucleophilic enough to react with E-SOSE. (c) 2007 Elsevier Ltd. All rights reserved.