(1S,2S)-1-(phenylsulfanyl)-2-(phenylselanyl)cyclohexane | 1022217-08-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1S,2S)-1-(phenylsulfanyl)-2-(phenylselanyl)cyclohexane
• 英文别名: [(1S,2S)-2-phenylselanylcyclohexyl]sulfanylbenzene
• CAS: 1022217-08-8
• 化学式: C₁₈H₂₀SSe
• 分子量: 347.383
• InChiKey: DYBZMSMFBISEPD-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯二硫醚 、 (+/-)-cis-2-(phenylseleno)-1-cyclohexanol 在 三丁基膦 作用下， 以 甲苯 为溶剂， 以42%的产率得到(1S,2S)-1-(phenylsulfanyl)-2-(phenylselanyl)cyclohexane
  参考文献：
  名称：

  Novel C2-symmetric chiral ligands: enantioselective transformation of cyclic 1,2-diols into 1,2-bis(phenylsulfenyl) and 1,2-bis(phenylselenyl) derivatives

  摘要：

  Chiral C-2-symmetric S,S- and Se,Se-donating ligands as well as the C-1 mixed S,Se-donating ligands were prepared from optically active 1,2-cyclohexanediol and 1,2-cyclopentanediol via the respective S(N)2 reactions. The bis(chalcogen) ligands obtained effectively catalyze the asymmetric allylic alkylation with enantioselectivities of up to 50% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.001

文献信息

• A highly selective thioselenation of olefins using disulfide-diselenide mixed system
  作者：Akiya Ogawa、Hiromichi Tanaka、Hiroshi Yokoyama、Ryoichi Obayashi、Kazuyuki Yokoyama、Noboru Sonoda

  DOI：10.1021/jo00027a021

  日期：1992.1

  A highly selective thioselenation of olefins has been attained by using a disulfide-diselenide mixed system. Upon irradiation through Pyrex with a tungsten lamp in the absence of solvent, the thioselenation of olefins 1 with diphenyl disulfide (2) and diphenyl diselenide (3) takes place to provide 1-(phenylthio)-2-(phenylseleno)alkanes 4 as a sole product in good yields. In the cases of terminal olefins, the thioselenation proceeds regioselectively. The cyclic olefins like cyclopentene and cyclohexene also undergo thioselenation to give corresponding E isomers stereoselectively. The reaction of the conjugate diene with diphenyl disulfide and diphenyl diselenide produces the 1,4-thioselenation adduct in good yield. The excellent regioselectivity observed in the thioselenation of the terminal olefins is due to the higher reactivity of PhS., compared with PhSe., toward carbon-carbon double bonds and the higher capturing ability of (PhSe)2, compared with (PhS)2, toward carbon radicals.