10,11-bis-triisopropylsilanylsulfanyl-undec-10-enoic acid methyl ester | 360055-68-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 10,11-bis-triisopropylsilanylsulfanyl-undec-10-enoic acid methyl ester
• 英文别名: methyl (Z)-10,11-bis[tri(propan-2-yl)silylsulfanyl]undec-10-enoate
• CAS: 360055-68-1
• 化学式: C₃₀H₆₂O₂S₂Si₂
• 分子量: 575.124
• InChiKey: MWJYQFDBWVDXGG-IADYIPOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.94
• 重原子数：
  36
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10,11-bis-triisopropylsilanylsulfanyl-undec-10-enoic acid methyl ester 在 盐酸 、 zinc trifluoromethanesulfonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以83%的产率得到dimethyl 9,9'-(2,5,7-trithiabicyclo[2.2.1]heptane-1,4-diyl)dinonanoate
  参考文献：
  名称：

  由1，2-双-三异丙基硅烷基硫基硫烷基制备2,5,7-三噻二环[2.2.1]庚烷。

  摘要：

  [反应：见正文]相对未开发1，2-双三异丙基甲硅烷基硫烷基的化学行为，弱的硫-硅键引起各种转化。在酸性条件（HCl）下和在室温下路易斯酸的存在下，以良好的产率获得双环加合物2。通过X射线晶体分析，其中R ＝苄基，确认了结构。

  DOI：

  10.1021/ol0524858
• 作为产物：
  描述：

  三异丙基硅烷硫醇 在 四(三苯基膦)钯 、 碘 、 sodium hydride 作用下， 以 甲苯 、 苯 为溶剂， 反应 15.0h， 生成 10,11-bis-triisopropylsilanylsulfanyl-undec-10-enoic acid methyl ester
  参考文献：
  名称：

  Preparation and reactivity studies of 1,2-bis-triisopropylsilanylsulfanyl-alkenes

  摘要：

  The cross-coupling reaction of bis-triisopropylsilyl disulfide 1 on alkynes yielded 1,2-bis-triisopropylsilanylsulfanyl-alkenes 2, a new chemical class. A series of tri and tetrasubstituted olefins 2 were prepared and their behavior toward electrophiles was studied. The triisopropylsilyl groups could be readily removed by treatment with TBAF at 0 degreesC for 1 h or cesium acetate at 70 degreesC for 2 h. Soft and hard electrophiles were submitted to 2 under these conditions. The electrophiles can either react to yield double addition products with alkyl and activated halides, epoxides and acyl chlorides or cyclic adducts with chloroformate derivatives. In the latter case, 1,3-dithiol-2-ones or 1,3-dithiol-2-thiones are prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00517-8

文献信息

• Preparation of 1,3-Dithiol-2-ones from 1,2-Bis-triisopropylsilanylsulfanyl Alkenes Under Mild Acidic Conditions
  作者：Yves Gareau、Hélène Juteau

  DOI：10.1080/10426500307851

  日期：2003.5.1

  1,2-Bis-triisopropylsilanylsulfanyl alkenes are readily converted to 1,3-dithiol-2-ones with phosgene under very mild acidic conditions at room temperature.
• Preparation and reactivity studies of 1,2-bis-triisopropylsilanylsulfanyl-alkenes
  作者：Yves Gareau、Mélanie Tremblay、Danny Gauvreau、Hélène Juteau

  DOI：10.1016/s0040-4020(01)00517-8

  日期：2001.7

  The cross-coupling reaction of bis-triisopropylsilyl disulfide 1 on alkynes yielded 1,2-bis-triisopropylsilanylsulfanyl-alkenes 2, a new chemical class. A series of tri and tetrasubstituted olefins 2 were prepared and their behavior toward electrophiles was studied. The triisopropylsilyl groups could be readily removed by treatment with TBAF at 0 degreesC for 1 h or cesium acetate at 70 degreesC for 2 h. Soft and hard electrophiles were submitted to 2 under these conditions. The electrophiles can either react to yield double addition products with alkyl and activated halides, epoxides and acyl chlorides or cyclic adducts with chloroformate derivatives. In the latter case, 1,3-dithiol-2-ones or 1,3-dithiol-2-thiones are prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Preparation of 2,5,7-Trithiabicyclo[2.2.1]heptane from 1,2-Bis-triisopropylsilanylsulfanyl Alkenes
  作者：Yves Gareau、Hélène Juteau、Nancy N. Tsou、Richard G. Ball

  DOI：10.1021/ol0524858

  日期：2006.1.1

  [reaction: see text] The chemical behavior of 1,2-bis-triisopropylsilanylsulfanyl alkenes 1 is relatively unexplored, and the weak sulfur-silicon bonds give rise to various transformations. Under acidic conditions (HCl) and in the presence of a Lewis acid at room temperature the bicyclic adduct 2 is obtained in good yield. The structure was confirmed by X-ray crystal analysis with R = benzyl.

  [反应：见正文]相对未开发1，2-双三异丙基甲硅烷基硫烷基的化学行为，弱的硫-硅键引起各种转化。在酸性条件（HCl）下和在室温下路易斯酸的存在下，以良好的产率获得双环加合物2。通过X射线晶体分析，其中R ＝苄基，确认了结构。