(S₂,R_S)-2-p-Tolylsulfinylcyclohexanone | 83859-17-0

• 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: (S₂,R_S)-2-p-Tolylsulfinylcyclohexanone
• 英文别名: (S₂R_S)-2-p-tolylsulfinylcyclohexanone；(2S,R_S)-2-p-tolylsulphinylcyclohexanone；[2S,(S)R]-2-(p-Tolylsulfinyl)cyclohexanone；(2S,(S)R)-2-p-tolylsulfinylcyclohexanone；2-p-tolylsulphinyl cyclohexanone；(2S)-2-[(R)-(4-methylphenyl)sulfinyl]cyclohexan-1-one
• CAS: 83859-17-0
• 化学式: C₁₃H₁₆O₂S
• 分子量: 236.335
• InChiKey: KVGRBFQZGQWCFQ-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (S₂,R_S)-2-p-Tolylsulfinylcyclohexanone 在 二异丁基氢化铝 作用下， 以86%的产率得到(S₁S₂R_S)-2-p-tolylsulfinylcyclohexanol
  参考文献：
  名称：

  手性亚磺酰基环己酮的合成与还原

  摘要：

  （ - - ） -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。

  DOI：

  10.1016/s0040-4039(00)96645-0
• 作为产物：
  描述：

  (2R,R_S)-2-p-tolylsulphinylcyclohexanone 生成 (S₂,R_S)-2-p-Tolylsulfinylcyclohexanone
  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

• 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。
• Highly diastereoselective Hydrocyanation of α-sulfinyl cycloalkanones
  作者：Ana Escribano、José L. García Ruano、Ana M. Martín Castro、Jesús H. Rodríguez

  DOI：10.1016/s0040-4020(01)90484-3

  日期：——

  Hydrocyanation of cyclic alpha-sulfinyl ketones under different conditions has been studied. The obtained results show that compounds derived from cyclohexanone react with Et(2)AlCN yielding only sulfinyl cyanohydrins exhibiting different configurations at sulfur and at hydroxylic carbon. The stereoselectivity is slightly lower but also very high starting from alpha-sulfinyl cyclopentanones. The influence of Lewis acids as well as the stereochemical course of these reactions have also been discussed.
• Bueno, Ana B.; Carreno, M. Carmen; Ruano, Jose L. Garcia, Anales de Quimica, 1994, vol. 90, # 7-8, p. 442 - 451
  作者：Bueno, Ana B.、Carreno, M. Carmen、Ruano, Jose L. Garcia

  DOI：——

  日期：——
• Reactions of chiral 2-p-tolylsulfinycycloalkanones with AlMe3
  作者：Ana B Bueno、M Carmen Carreño、Jean Fischer、J.L García Ruano、Begoña Peña、Lorenzo Peñas、Almudena Rubio

  DOI：10.1016/s0040-4039(00)79719-x

  日期：1991.7

  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%.
• Enantioselective Generation of Benzylic Stereocenters Mediated by a Remote Sulfoxide
  作者：José L. García Ruano、M. Carmen Carreño、Miguel A. Toledo、José M. Aguirre、M. Teresa Aranda、Jean Fischer

  DOI：10.1002/1521-3773(20000804)39:15<2736::aid-anie2736>3.0.co;2-m

  日期：2000.8.4