(S₂,R_S)-2-p-Tolylsulfinylcyclopentanone | 124819-68-7

• 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: (S₂,R_S)-2-p-Tolylsulfinylcyclopentanone
• 英文别名: (2S)-2-[(R)-(4-methylphenyl)sulfinyl]cyclopentan-1-one
• CAS: 124819-68-7
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: HIHFDGSOXNGCTH-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甲基铝 、 (S₂,R_S)-2-p-Tolylsulfinylcyclopentanone 以 正己烷 、 甲苯 为溶剂， 以98%的产率得到(R₁,S₂,R_S)-1-Methyl-2-p-tolylsulfinylcyclopentanol
  参考文献：
  名称：

  Reactions of chiral 2-p-tolylsulfinycycloalkanones with AlMe3

  摘要：

  The reactions of (S2,Rs) and (R2,Rs)-2-p-tolylsulfinylcyclohexanones with AlMe3/ZnCl2 only yield the cyclohexylmethylcarbinols with R configuration at hydroxylic carbon. The (R1,S2,Rs)-1-methyl-2-p-tolylsulfinylcyclopentanol was the only compound obtained in the reaction of Me3Al with both epimeric 2-p-tolylsulfinylcyclopentanones. The d.e. of both reactions are higher than 96%.

  DOI：

  10.1016/s0040-4039(00)79719-x
• 作为产物：
  描述：

  Phenyl-[2-(toluene-4-sulfinyl)-cyclopent-(E)-ylidene]-amine 在 硫酸 作用下， 以 乙醚 为溶剂， 生成 (2R,R_S)-2-p-tolylsulphinylcyclopentanone 、 (S₂,R_S)-2-p-Tolylsulfinylcyclopentanone
  参考文献：
  名称：

  Carreno, M. Carmen; Ruano, Jose L. Garcia; Pedregal, Concepcion, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1335 - 1337

  摘要：

  DOI：

文献信息

• 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.
• CARMEN, CARRENO M.;GARCIA, RUANO JOSE L.;PEDREGAL, CONCEPCION;RUBIO, ALMU+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 1335-1337
  作者：CARMEN, CARRENO M.、GARCIA, RUANO JOSE L.、PEDREGAL, CONCEPCION、RUBIO, ALMU+

  DOI：——

  日期：——