(R₁R₂R_S)-2-p-tolylsulfinylcyclohexanol | 116049-68-4

• 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: (R₁R₂R_S)-2-p-tolylsulfinylcyclohexanol
• 英文别名: (1R,2R)-2-[(R)-(4-methylphenyl)sulfinyl]cyclohexan-1-ol
• CAS: 116049-68-4
• 化学式: C₁₃H₁₈O₂S
• 分子量: 238.351
• InChiKey: NQEMHDDYIOYJSI-IOASZLSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (2R,R_S)-2-p-tolylsulphinylcyclohexanone 生成 (R₁R₂R_S)-2-p-tolylsulfinylcyclohexanol
  参考文献：
  名称：

  CARRENO, M. C.;RUANO, J. L. GARCIA;RUBIO, A., TETRAHEDRON LETT., 28,(1987) N 41, 4861-4864

  摘要：

  DOI：

文献信息

• Stereocontrolled Reduction of 2-(<i>p</i>-Tolylsulfinyl)cycloalkanones under Basic Conditions: π-Facial Selection in Cyclic Systems Directed by a Chiral Side Chain
  作者：Katsuyuki Ogura、Michio Ishida、Makoto Fujita

  DOI：10.1246/bcsj.62.3987

  日期：1989.12

  Reduction of a 2-(p-tolylsulfinyl)cycloalkanone with sodium borohydride in methanol–triethylamine is accompanied by rapid epimerization at C2. Under the conditions employed here, the π-facial selectivity of the reduction is directed by the side chain chirality and, among four possible isomers of the corresponding cycloalkanol, one isomer is given with high selectivities up to 85%.

  用硼氢化钠在甲醇-三乙胺中还原2-(p-甲苯硫酰基)环烷酮时，C2处会迅速发生表异构化。在这里采用的条件下，减肥的π面选择性受侧链手性影响，在相应的环烷醇的四种可能异构体中，有一种异构体的选择性高达85%。
• Synthesis and reduction of chiral sulfinyl cyclohexanones
  作者：M.C. Carreño、J.L.García Ruano、A. Rubio

  DOI：10.1016/s0040-4039(00)96645-0

  日期：1987.1

  The reaction of cyclohexanone with (S)-(−)-menthyl-p-toluenesulfinate in the presence of Pri2NMgBr yields a mixture of enantiomerically pure 2-p-tolylsulfinylcyclohexanone diastereoisomers. Their stereoselective reduction to chiral hydroxysulfoxides is also reported.

  （ - - ） -环己酮与（S）的反应薄荷基对甲苯以Pr存在我2 NMgBr得到对映体纯2-对非对映异构tolylsulfinylcyclohexanone的混合物。还报道了它们的立体选择性还原为手性羟基亚砜。
• Stereoselective hydride reductions of chiral 2-p-tolylsulfinylcycloalkanones
  作者：Ana B. Bueno、M. Carmen Carreño、Jose L. García Ruano、Begoña Peña、Almudena Rubio、Miguel A. Hoyos

  DOI：10.1016/s0040-4020(01)85512-5

  日期：——

  The highly stereoselective hydride reductions of chiral 2-p-tolylsulfinyl-cyclopentanones and cycloheptanones are described. With DIBAL (electrophilic hydride) the configuration induced at C-1 is controlled by the sulfinyl group (1,3-asymmetric induction), and it can be inverted by using ZnCl2 as catalyst. With L-selectride the stereoselectivity is directed by the C-2 chiral groups (1,2-asymmetric induction). Other nucleophilic hydrides gave results which depend on the reagents and the size of the rings.