(1R,2S,5S,6R,R_S)-6-fluoro-5-methyl-2-<(4-methylphenyl)sulphinyl>cyclohexan-1-ol | 139965-03-0

• 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: (1R,2S,5S,6R,R_S)-6-fluoro-5-methyl-2-<(4-methylphenyl)sulphinyl>cyclohexan-1-ol
• 英文别名: (1R,2R,3S,6S,R_S)-2-Fluoro-3-methyl-6-<(4-methylphenyl)sulfinyl>cyclohexan-1-ol；(1R,2R,3S,6S)-2-fluoro-3-methyl-6-[(R)-(4-methylphenyl)sulfinyl]cyclohexan-1-ol
• CAS: 139965-03-0
• 化学式: C₁₄H₁₉FO₂S
• 分子量: 270.368
• InChiKey: SGMQGHUHIHDVDB-GWVBSCTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (1R,2S,5S,6R,R_S)-6-fluoro-5-methyl-2-<(4-methylphenyl)sulphinyl>cyclohexan-1-ol 在 sodium hydride 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (3S,4R,5S)-3-(Benzyloxy)-4-fluoro-5-methylcyclohex-1-ene
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure Fluoro- and gem-Chlorofluorocyclohexane Derivatives

  摘要：

  gem-Chloronuorocyclohexanols 10 are prepared in good yields by radical-promoted cyclization from the corresponding omega-dichlorofluoroheptenols 4. Fluorocyclohexanols 11 are obtained either from 10 or in a single step from open-chain alcohols 4. The stereochemical outcome of both the radical cyclization and the reductive dechlorination is discussed. Elimination of the chiral auxiliary sulfinyl group and appropriate elaborations afford enantiomerically pure derivatives 12-17. Relative and absolute configurations as well as preferred conformations in solution for all final compounds are provided.

  DOI：

  10.1021/jo00100a057
• 作为产物：
  描述：

  (+)-(R_S)-5-<(4-Methylphenyl)sulfinyl>pent-1-ene 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 ammonium hydroxide 、 苯 为溶剂， 反应 20.25h， 生成 (1R,2S,5S,6R,R_S)-6-fluoro-5-methyl-2-<(4-methylphenyl)sulphinyl>cyclohexan-1-ol
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure Fluoro- and gem-Chlorofluorocyclohexane Derivatives

  摘要：

  gem-Chloronuorocyclohexanols 10 are prepared in good yields by radical-promoted cyclization from the corresponding omega-dichlorofluoroheptenols 4. Fluorocyclohexanols 11 are obtained either from 10 or in a single step from open-chain alcohols 4. The stereochemical outcome of both the radical cyclization and the reductive dechlorination is discussed. Elimination of the chiral auxiliary sulfinyl group and appropriate elaborations afford enantiomerically pure derivatives 12-17. Relative and absolute configurations as well as preferred conformations in solution for all final compounds are provided.

  DOI：

  10.1021/jo00100a057

文献信息

• On the synthesis of optically pure monofluorocyclohexanol derivatives by the fluorinated sulfoxide chiron route
  作者：Alberto Arnone、Pierfrancesco Bravo、Massimo Frigerio、Fiorenza Viani、Giancarlo Cavicchio、Marcello Crucianelli

  DOI：10.1016/s0040-4020(01)89545-4

  日期：1994.1

  Monofluorocyclohexanols 1 are obtained in optically pure form through radical cyclization of gem-chlorofluoroheptenols 2 which derive from the condensation of α-lithium derivative of sulfoxide 3 on racemic ethyl chlorofluoroacetate 4, and hydride-promoted reduction of the intermediate ketones 5. Some considerations on the stereochemical course of the radical promoted cyclization reaction follow.

  Monofluorocyclohexanols 1是光学纯形式通过偕- chlorofluoroheptenols的自由基环化得到2从亚砜的α -锂衍生物的缩合得到3上外消旋乙基chlorofluoroacetate 4，和氢化促进的还原中间体酮5。自由基促进环化反应的立体化学过程的一些考虑如下。
• Synthesis of optically pure fluoro- and gem-chlorofluoro-cyclohexane derivatives by intramolecular trapping of dihaloalkyl radicals.
  作者：Alberto Arnone、Pierfrancesco Bravo、Giancarlo Cavicchio、Massimo Frigerio、Fiorenza Viani

  DOI：10.1016/s0957-4166(00)82303-4

  日期：1992.1

  gem-Chlorofluorocyclohexanols 8 bearing a methyl and a p-tolylsulphinyl substituent have been obtained in optically pure form by radical cyclization of the corresponding halo-alkenes 4. Reductive dechlorination of both (6R)- and (6S)-8 gave fluoroderivative (6R)-9, which through functional group elaborations gave the hydroxyfluoro- and trihydroxyfluoro-cyclohexane derivatives 12 and 15.