S-tert-butyl-S-(2-methylthiophenyl)sulfoximine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-tert-butyl-S-(2-methylthiophenyl)sulfoximine
• 英文别名: Tert-butyl-imino-(2-methylsulfanylphenyl)-oxo-lambda6-sulfane；tert-butyl-imino-(2-methylsulfanylphenyl)-oxo-λ6-sulfane
• 化学式: C₁₁H₁₇NOS₂
• 分子量: 243.394
• InChiKey: SFRHDIKIJKAAEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  S-(tert-butyl)-S-phenylsulfoximine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.84h， 生成 S-tert-butyl-S-(2-methylthiophenyl)sulfoximine
  参考文献：
  名称：

  ortho-Lithiation of S-tert-butyl-S-phenylsulfoximines. New route to enantiopure sulfinamides via a de-tert-butylation reaction

  摘要：

  The sulfoximine group proved to be an excellent ortho-directing group in lithiation reactions. Several electrophiles were used to afford the corresponding ortho-functionalized aryl sulfoximines in good yields. The use of prochiral electrophiles lead to modest to good diastereoselectivities up to 95%. During this study, we observed a side reaction due to a S-de-tert-butylation. After optimization of this S-de-tert-butylation reaction, the corresponding enantiopure sulfinamides could be obtained in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.047

文献信息

• The tert-butyl sulfoximine group as an effective ortho-director of lithiation: ortho-metallated S-(tert-butyl)-S-phenylsulfoximines
  作者：V. Levacher、B.Langer Eriksen、M. Begtrup、G. Dupas、G. Quéguiner、J. Duflos、J. Bourguignon

  DOI：10.1016/s0040-4039(99)00060-x

  日期：1999.2

  The readily available S-(tert-butyl)-N-(trimethylsilyl)-S-phenylsulfoximine was prepared from S-methyl-N(trimethylsilyl)-S-phenylsulfoximine via lithiation-methylation sequences. The reaction with n-butyllithium in THF at -78 degrees C afforded the corresponding ortho-lithiated species which could be trapped with different electrophiles in good yields. Addition of benzaldehyde proceeded with a modest diastereoselectivity (de=52%). (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• ortho-Lithiation of S-tert-butyl-S-phenylsulfoximines. New route to enantiopure sulfinamides via a de-tert-butylation reaction
  作者：Stéphane Gaillard、Cyril Papamicaël、Georges Dupas、Francis Marsais、Vincent Levacher

  DOI：10.1016/j.tet.2005.06.047

  日期：2005.8

  The sulfoximine group proved to be an excellent ortho-directing group in lithiation reactions. Several electrophiles were used to afford the corresponding ortho-functionalized aryl sulfoximines in good yields. The use of prochiral electrophiles lead to modest to good diastereoselectivities up to 95%. During this study, we observed a side reaction due to a S-de-tert-butylation. After optimization of this S-de-tert-butylation reaction, the corresponding enantiopure sulfinamides could be obtained in good yields. (c) 2005 Elsevier Ltd. All rights reserved.