trans-5,6-bis(methylthio)cyclooctene | 137742-53-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: trans-5,6-bis(methylthio)cyclooctene
• 英文别名: trans-5,6-Bis(methylthio)cyclooct-1-ene；(1Z,5R,6R)-5,6-bis(methylsulfanyl)cyclooctene
• CAS: 137742-53-1
• 化学式: C₁₀H₁₈S₂
• 分子量: 202.385
• InChiKey: WGOXOGDJWSXFEV-HWKXXFMVSA-N

物化性质

• 沸点：
  301.2±42.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 、 二甲基二硫 在 三氟化硼-二甲醚络合物 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 0.5h， 以18%的产率得到trans-5,6-bis(methylthio)cyclooctene
  参考文献：
  名称：

  Boron trifluoride catalyzed addition of disulfides to alkenes

  摘要：

  DOI：

  10.1021/jo00222a041

文献信息

• Synthesis of fluoroalkyl methyl thioethers by formal addition of methanesulfenyl fluoride to alkenes
  作者：Gunter Haufe、Gerard Alvernhe、Daniel Anker、Andre Laurent、Christine Saluzzo

  DOI：10.1021/jo00028a056

  日期：1992.1

  The electrophilic anti-1,2-addition of the elements of methanesulfenyl fluoride to carbon-carbon double bonds by a one-pot reaction of dimethyl(methylthio)sulfonium tetrafluoroborate and triethylamine trishydrofluoride with various types of alkenes is used for the synthesis of beta-fluoroalkyl methyl thioethers. This reaction is stereospecific: starting from cis-cycloalkenes (1) trans-1-fluoro-2-(methylthio)cycloalkanes (2) are formed, while trans-cyclododecene (3) gives the cis product 4 everytime in good yields. With unsymmetrical alkenes these reactions proceed regioselectively to produce Markovnikov-oriented fluoro thioethers. With 2,6-norbornadiene (26) exclusive exo attack on one double bond and subsequent transannular participation of the second pi-bond gives rise to two isomeric 3,5-disubstituted nortricyclanes, 28 and 29, while starting from the medium-sized cis,cis-1,5-cyclooctadiene (10) no transannular pi-participation is observed: the trans-1,2-addition product to one of the two double bonds in 11 is isolated. In contrast, in the reaction of the monoepoxide 30 of this diene in addition to the simple 1,2-adduct 31 a transannular oxygen participation occurs producing three oxa bicyclic compounds 32-34. The oxidation of 1-fluoro-2-(methylthio)cyclooctane (2a) by sodium periodate yields the expected mixture of two diastereomeric 1-fluoro-2-(methylsulfinyl)cyclooctanes (36) which on pyrolysis give 3-fluorocyclooctene (37).
• CASERIO, M. C.;FISHER, C. L.;KIM, J. K., J. ORG. CHEM., 1985, 50, N 22, 4390-4393
  作者：CASERIO, M. C.、FISHER, C. L.、KIM, J. K.

  DOI：——

  日期：——
• Boron trifluoride catalyzed addition of disulfides to alkenes
  作者：Marjorie C. Caserio、Cindy L. Fisher、Jhong K. Kim

  DOI：10.1021/jo00222a041

  日期：1985.11