S-tert-butyl-N-trimethylsilyl-S-phenylsulfoximine | 222306-91-4

• 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: S-tert-butyl-N-trimethylsilyl-S-phenylsulfoximine
• 英文别名: S-methyl-N-trimethylsilyl-S-phenylsulfoximine；[(Tert-butyl-oxo-phenyl-lambda6-sulfanylidene)amino]-trimethylsilane；[(tert-butyl-oxo-phenyl-λ6-sulfanylidene)amino]-trimethylsilane
• CAS: 222306-91-4
• 化学式: C₁₃H₂₃NOSSi
• 分子量: 269.483
• InChiKey: MCHOMAIPKYBAPG-UHFFFAOYSA-N

物化性质

• 沸点：
  330.0±25.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-tert-butyl-N-trimethylsilyl-S-phenylsulfoximine 在 正丁基锂 、 magnesium(II) perchlorate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 26.17h， 以71%的产率得到S-(2-trimethylsilylphenyl)benzenesulfinamide
  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
• 作为产物：
  描述：

  甲基苯基亚砜 在 正丁基锂 、 iron(III)-acetylacetonate 、 亚碘酰苯 、 caesium carbonate 、 苯硫酚 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 0.5h， 生成 S-tert-butyl-N-trimethylsilyl-S-phenylsulfoximine
  参考文献：
  名称：

  叔丁基邻三甲基甲硅烷基苯基亚砜亚胺的意外环化反应

  摘要：

  描述了从甲基苯基亚砜亚胺开始的标题化合物 5 的有效一锅法合成。在尝试使用氯化碘对该化合物进行碘脱甲硅烷化时，硅原子上的一个甲基在形式上被亚氨基氮取代，得到新型杂环系统 1,3,2-苯并噻唑唑的衍生物 8。

  DOI：

  10.3998/ark.5550190.0013.309

文献信息

• Sulfoximines: A Reusable Directing Group for Chemo- and Regioselective ortho CH Oxidation of Arenes
  作者：M. Ramu Yadav、Raja K. Rit、Akhila K. Sahoo

  DOI：10.1002/chem.201200092

  日期：2012.4.27

  Sulfoximines direct: A new protocol for the chemo‐ and regioselective ortho CH acetoxylation of arenes in N‐benzoylated sulfoximines is reported. The sulfoximine directing group is easily detached from the CH oxidation product through acid‐promoted hydrolysis, isolated, and reused (see scheme). The meta‐substituted phenols are synthesized following this strategy and the stereointegrity of the sulfoximine

  亚磺酰亚胺直接：用于化疗和区域选择性的新协议邻Ç 中的H芳烃的乙酰氧基化Ñ报道-benzoylated亚磺酰亚胺。通过酸促进的水解作用，磺胺嘧啶导向基很容易从CH氧化产物中分离出来，进行分离和再利用（参见方案）。该元取代酚遵循这一发展战略和亚砜的stereointegrity在这一转变被保留合成。还证明了甲基的C（sp 3）H乙酰氧基化。
• 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.
• An unexpected cyclization reaction of tert-butyl o-trimethylsilylphenyl sulfoximine
  作者：Jörg Christoph Schmidt、Gunadi Adiwidjaja、Ernst Schaumann

  DOI：10.3998/ark.5550190.0013.309

  日期：——

  An efficient one-pot synthesis of the title compound 5 starting from methyl phenyl sulfoximine is described. On attempted iododesilylation of this compound using iodine chloride, one methyl group on the silicon atom is formally replaced by the imino nitrogen to give a derivative 8 of the novel heterocyclic system 1,3,2-benzothiasilazole.

  描述了从甲基苯基亚砜亚胺开始的标题化合物 5 的有效一锅法合成。在尝试使用氯化碘对该化合物进行碘脱甲硅烷化时，硅原子上的一个甲基在形式上被亚氨基氮取代，得到新型杂环系统 1,3,2-苯并噻唑唑的衍生物 8。
• 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.