(2S,3R,R_s)-1,1-dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>hex-5-en-2-ol | 151775-83-6

• 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: (2S,3R,R_s)-1,1-dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>hex-5-en-2-ol
• 英文别名: (2S,3R)-1,1-dichloro-1-fluoro-3-[(R)-(4-methylphenyl)sulfinyl]hex-5-en-2-ol
• CAS: 151775-83-6
• 化学式: C₁₃H₁₅Cl₂FO₂S
• 分子量: 325.231
• InChiKey: HJJGFFZJITXLKP-UFYHVXEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,R_s)-1,1-dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>hex-5-en-2-ol 在 三氟乙酸酐 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 0.17h， 生成 (2S,3R)-1,1-dichloro-1-fluoro-3-<(4-methylphenyl)thio>hex-5-en-2-ol
  参考文献：
  名称：

  Asymmetric synthesis of gem-chlorofluorocyclopentane derivatives by intramolecular trapping of dihaloalkyl radicals

  摘要：

  Radical promoted cyclization of enantiomerically pure substituted 1,1-dichloro-1-fluoro-3-[(4-methylphenyl)sulfinyl]hex-5-en-2-ols (6) afforded the title compounds 12 in good overall yields. The regio and stereochemical outcome of the cyclizations are explained by considering the respective transition states. The structure and configuration of the products were elucidated with the aid of H-1, C-13 and F-19 NMR spectra and H-1-{H-1} and H-1-{F-19} NOE difference experiments.

  DOI：

  10.1016/s0040-4020(01)80430-0
• 作为产物：
  描述：

  (-)-menthyl p-toluenesulfinate 在 碘 、 magnesium 作用下， 反应 2.5h， 生成 (2S,3R,R_s)-1,1-dichloro-1-fluoro-3-<(4-methylphenyl)sulfinyl>hex-5-en-2-ol
  参考文献：
  名称：

  Asymmetric synthesis of gem-chlorofluorocyclopentane derivatives by intramolecular trapping of dihaloalkyl radicals

  摘要：

  Radical promoted cyclization of enantiomerically pure substituted 1,1-dichloro-1-fluoro-3-[(4-methylphenyl)sulfinyl]hex-5-en-2-ols (6) afforded the title compounds 12 in good overall yields. The regio and stereochemical outcome of the cyclizations are explained by considering the respective transition states. The structure and configuration of the products were elucidated with the aid of H-1, C-13 and F-19 NMR spectra and H-1-{H-1} and H-1-{F-19} NOE difference experiments.

  DOI：

  10.1016/s0040-4020(01)80430-0

文献信息

• Asymmetric synthesis of gem-chlorofluorocyclopentane derivatives by intramolecular trapping of dihaloalkyl radicals
  作者：Alberto Arnone、Piefrancesco Bravo、Giancarlo Cavicchio、Massimo Frigerio、Fiorenza Viani

  DOI：10.1016/s0040-4020(01)80430-0

  日期：1993.7

  Radical promoted cyclization of enantiomerically pure substituted 1,1-dichloro-1-fluoro-3-[(4-methylphenyl)sulfinyl]hex-5-en-2-ols (6) afforded the title compounds 12 in good overall yields. The regio and stereochemical outcome of the cyclizations are explained by considering the respective transition states. The structure and configuration of the products were elucidated with the aid of H-1, C-13 and F-19 NMR spectra and H-1-H-1} and H-1-F-19} NOE difference experiments.