(1R,2S)-1-Ethynyl-2-phenylsulfanyl-cyclohexanol | 145117-27-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1R,2S)-1-Ethynyl-2-phenylsulfanyl-cyclohexanol
• 英文别名: (1R,2S)-1-ethynyl-2-phenylsulfanylcyclohexan-1-ol
• CAS: 145117-27-7
• 化学式: C₁₄H₁₆OS
• 分子量: 232.346
• InChiKey: QXTHMIUISOUPTQ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1-Ethynyl-2-phenylsulfanyl-cyclohexanol 生成 (E/Z)-<2-(phenylthio)cyclohexylidene>ethanal
  参考文献：
  名称：

  共轭烯炔的共氧化。方便合成β-亚砜氧基炔醇

  摘要：

  通过将巯基和氧加到共轭烯炔上来制备几种β-亚砜氧基取代的炔醇。

  DOI：

  10.1016/s0040-4039(00)61088-2
• 作为产物：
  描述：

  苯硫酚 、 1-乙炔基环己烷 在 氧气 作用下， 以 正庚烷 为溶剂， 以26%的产率得到1-ethynyl-2-(phenylsulfinyl)cyclohexanol
  参考文献：
  名称：

  共轭烯炔的共氧化。方便合成β-亚砜氧基炔醇

  摘要：

  通过将巯基和氧加到共轭烯炔上来制备几种β-亚砜氧基取代的炔醇。

  DOI：

  10.1016/s0040-4039(00)61088-2

文献信息

• [2,3]-Sigmatropic rearrangement of .beta.-phenylsulfonyl propargylic sulfenates as a method for preparing 1,4-bis(phenylsulfonyl)-1,3-butadienes
  作者：Xiaoheng Wang、Zhijie Ni、Xiujing Lu、Andrea Hollis、Harold Banks、Augusto Rodriguez、Albert Padwa

  DOI：10.1021/jo00072a019

  日期：1993.9

  Several beta-sulfoxy-substituted acetylenic carbinols were prepared by the addition of thiyl radicals and oxygen to conjugated enynes. The products obtained are derived from thiyl radical attack at the olefinic bond to generate a propargylic radical. Capture of this radical by oxygen followed by hydrogen transfer from thiophenol gives a hydroperoxide intermediate, which undergoes oxygen transfer by both intra- and intermolecular pathways. The resultant beta-phenylsulfinyl propargylic alcohols proved to be versatile intermediates for the preparation of several different classes of compounds. The [2,3]-sigmatropic sulfinate to sulfoxide rearrangement was found to give 1,4-bis(phenylsulfonyl)-1,3-butadienes, alpha,beta-unsaturated phenylsulfoxy ketones, and beta-phenylsulfonyl alpha-allenic sulfoxides' Oxidation of the sulfoxy moiety to the sulfone followed by sulfinate formation with phenylsulfenyl chloride produces, after [2,3]-sigmatropic rearrangement, beta-phenylsulfonyl alpha-allenic sulfoxides. In certain cases these allenes could be isolated, but were usually isomerized in situ and further oxidized to give 1,4-bis(phenylsulfonyl)-1,3-butadienes. The [2,3]-sigmatropic rearrangement of beta-phenyl-sulfinyl-substituted propargylic alcohols proceeds by an entirely different course. With these systems, a double sigmatropic process occurs leading to the formation of vinyl sulfinates which are readily hydrolyzed to give alpha,beta-unsaturated phenylsulfoxy ketones.