(R_S)-2-[(4-methylphenyl)sulfinyl]-1-phenylpropan-1-one | 196928-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R_S)-2-[(4-methylphenyl)sulfinyl]-1-phenylpropan-1-one
• 英文别名: 2-[(R)-(4-methylphenyl)sulfinyl]-1-phenylpropan-1-one
• CAS: 196928-19-5
• 化学式: C₁₆H₁₆O₂S
• 分子量: 272.368
• InChiKey: HRRJXXDEFUYTET-GAGCMDECSA-N

物化性质

• 沸点：
  457.7±38.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (R_S)-2-[(4-methylphenyl)sulfinyl]-1-phenylpropan-1-one 在 sodium hydride 、 Selectfluor 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到2-Fluoro-1-phenyl-2-((S)-toluene-4-sulfinyl)-propan-1-one
  参考文献：
  名称：

  Mild α-fluorination of enantiomerically pure β-ketosulfoxides by F-TEDA-BF4

  摘要：

  A wide range of cu-sodium derivatives of chiral and enantiomerically pure beta-ketosulfoxides have been regioselectively fluorinated with the 'F+' fluorinating agent F-TEDA-BF4 without affecting the sulfinyl stereogenic center. alpha-Monofluoro-beta-ketosulfoxides produced in this reaction can undergo further fluorination providing the corresponding alpha,alpha-difluoro derivatives, easily transformed by deacylation into enantiomerically pure (S)-difluoromethyl-p-tolylsulfoxide. (C) 1997 Elsevier Science S.A.

  DOI：

  10.1016/s0022-1139(97)00035-3
• 作为产物：
  描述：

  (R)-p-tolylsulfinylacetophenone 、 碘甲烷 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (R_S)-2-[(4-methylphenyl)sulfinyl]-1-phenylpropan-1-one
  参考文献：
  名称：

  1,3-不对称诱导DIBAL / ZnBr 2还原α-烷基β-酮亚砜

  摘要：

  用DIBAL / ZnBr 2进行的手性α-烷基β-酮亚砜的高度立体选择性还原取决于硫的构型（1,3-诱导），而不是C-α的构型（1,2-诱导）。先前已有报道。这一事实大大增加了Solladié合成光学纯次生甲醇的方法的范围。那些降低羰基氧螯合ZnBr 2的能力的取代基引起立体选择性的降低。

  DOI：

  10.1016/s0040-4039(00)79069-1

文献信息

• Asymmetric synthesis of tertiary vinyl carbinols by highly stereoselective methylation of α-methyl-β-ketosulfoxides with aluminum reagents
  作者：José L Garcı́a Ruano、M Mercedes Rodrı́guez-Fernández、M.Carmen Maestro

  DOI：10.1016/j.tet.2004.05.016

  日期：2004.6

  configuration at C-α. The stereochemical pathway seems to be different with both reagents, thus affording a higher stereoselectivity with Me2AlCl. Pyrolytic desulfinylation and hydrogenolysis of the C–S bond allowed the transformation of the resulting hydroxysulfoxides into interesting optically pure tertiary methyl carbinols.

  报道了手性无环α-甲基-β-酮亚砜与Me 3 Al和Me 2 AlCl的甲基化。羟基碳上的诱导构型主要受亚磺酰基的构型控制，在大多数情况下，无论C-α上的构型如何，de均高于90％。两种试剂的立体化学途径似乎不同，因此对Me 2 AlCl具有更高的立体选择性。C–S键的热解脱亚甲基化和氢解作用使所生成的羟基亚砜转化为有趣的光学纯叔甲基甲醇。
• Highly diastereoselective hydrocyanation of .beta.-keto sulfoxides: synthesis of enantiomerically pure cyanohydrin derivatives
  作者：Jose L. Garcia Ruano、Ana M. Martin Castro、Jesus H. Rodriguez

  DOI：10.1021/jo00052a044

  日期：1992.12
• Synthesis of enantiomerically pure acyclic α-sulfinyl ketimines
  作者：José L Garcı́a Ruano、Antonio Lorente、Jesús H Rodrı́guez Ramos

  DOI：10.1016/s0957-4166(98)00211-0

  日期：1998.7

  Two different methods to obtain enantiomerically pure N-alkyl and N-aryl alpha-sulfinyl ketimines are reported. Reaction of enantiomerically pure alpha-sulfinyl ketones (1-6) with benzylamine or p-methoxyaniline, in the presence of molecular sieves (3 Angstrom), yields the corresponding of N-benzyl and N-p-methoxyphenyl ketimines (7A-12A and 7B-12B). Better results were achieved by alpha-sulfinylation of ketimines (13A-18A and 13B-18B) with (-)-menthyl p-toluenesulfinate in the presence of lithium (N-arylimines) or magnesium (N-benzylimines) bases. The different tautomeric behaviour of the obtained N-aryl and N-alkyl derivatives is reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• 1,3-asymmetric induction in the reduction ofα-alkyl β-Ketosulfoxides with DIBAL/ZnBr2
  作者：Barros M. David、Carmen Carreño、José L. Garcií Ruano、M.Carmen Maestro

  DOI：10.1016/s0040-4039(00)79069-1

  日期：1992.5

  reduction of chiral α-alkyl β-ketosulfoxides with DIBAL/ZnBr2 is governed by the configuration at the sulfur (1,3-induction) and not by that of the C-α (1,2-induction) as it has been previously reported. This fact considerably increases the scope of the Solladié's methodology to synthesize optically pure secondary carbinols. Those substituents decreasing the capability of the carbonyl oxygen to chelate

  用DIBAL / ZnBr 2进行的手性α-烷基β-酮亚砜的高度立体选择性还原取决于硫的构型（1,3-诱导），而不是C-α的构型（1,2-诱导）。先前已有报道。这一事实大大增加了Solladié合成光学纯次生甲醇的方法的范围。那些降低羰基氧螯合ZnBr 2的能力的取代基引起立体选择性的降低。
• Mild α-fluorination of enantiomerically pure β-ketosulfoxides by F-TEDA-BF4
  作者：Alberto Arnone、Pierfrancesco Bravo、Massimo Frigerio、Giuliana Salani、Fiorenza Viani、Matteo Zanda、Carmela Zappalà

  DOI：10.1016/s0022-1139(97)00035-3

  日期：1997.8

  A wide range of cu-sodium derivatives of chiral and enantiomerically pure beta-ketosulfoxides have been regioselectively fluorinated with the 'F+' fluorinating agent F-TEDA-BF4 without affecting the sulfinyl stereogenic center. alpha-Monofluoro-beta-ketosulfoxides produced in this reaction can undergo further fluorination providing the corresponding alpha,alpha-difluoro derivatives, easily transformed by deacylation into enantiomerically pure (S)-difluoromethyl-p-tolylsulfoxide. (C) 1997 Elsevier Science S.A.