(S)-dimethylsulfonium (p-tolylsulfinyl)methylide | 889132-62-1

• 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)-dimethylsulfonium (p-tolylsulfinyl)methylide
• 英文别名: dimethyl-[[(S)-(4-methylphenyl)sulfinyl]methylidene]-lambda4-sulfane；dimethyl-[[(S)-(4-methylphenyl)sulfinyl]methylidene]-λ4-sulfane
• CAS: 889132-62-1
• 化学式: C₁₀H₁₄OS₂
• 分子量: 214.353
• InChiKey: DWPCARKVEDPBDW-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-dimethylsulfonium (p-tolylsulfinyl)methylide 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 24.67h， 生成 甲基对甲苯亚砜
  参考文献：
  名称：

  Highly stereoselective aziridination of imines with (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide

  摘要：

  Addition of (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide to N-tosyl imines afforded the corresponding sulfinyl aziridines with full enantio- and diastereoselectivity. The chiral sulfinyl substituent was removed without ring opening leading to enantiopure 2-substituted aziridines. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.117
• 作为产物：
  描述：

  (S)-dimethylsulfonium(p-tolylsulfinyl)methane tetrafluoroborate 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以100%的产率得到(S)-dimethylsulfonium (p-tolylsulfinyl)methylide
  参考文献：
  名称：

  (S)-Dimethylsulfonium(p-tolylsulfinyl)methylide：一种新的手性锍Ylide及其在不对称环氧化中的应用

  摘要：

  标题光学活性锍叶立德是通过容易获得的 (-)-(S)-p-甲苯基甲硫基甲基亚砜的甲基化和随后的去质子化制备的。它与醛类反应得到具有完全对映选择性和中等非对映选择性的 α,β-环氧亚砜。简要讨论了亚磺酰基环氧乙烷酸催化重排的空间过程。

  DOI：

  10.1055/s-2006-933131

文献信息

• (<i>S</i>)-Dimethylsulfonium(<i>p</i>-tolylsulfinyl)methylide: A New Chiral Sulfonium Ylide and its Use in Asymmetric Epoxidation
  作者：Wanda H. Midura

  DOI：10.1055/s-2006-933131

  日期：——

  The title optically active sulfonium ylide was prepared by methylation of easily available (-)-(S)-p-tolylmethylthiomethyl-sulfoxide and subsequent deprotonation. Its reaction with aldehydes gave α,β-epoxy sulfoxides with full enantioselectivity and moderate diastereoselectivity. The steric course of acid-catalyzed rearrangement of sulfinyl oxiranes is briefly discussed.

  标题光学活性锍叶立德是通过容易获得的 (-)-(S)-p-甲苯基甲硫基甲基亚砜的甲基化和随后的去质子化制备的。它与醛类反应得到具有完全对映选择性和中等非对映选择性的 α,β-环氧亚砜。简要讨论了亚磺酰基环氧乙烷酸催化重排的空间过程。
• Limitations, mechanism and understanding of the origins of stereocontrol in (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide-mediated epoxidation reactions
  作者：Wanda H. Midura、Marek Cypryk

  DOI：10.1016/j.tetasy.2010.01.012

  日期：2010.2

  The reaction of the (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide with aldehydes gave alpha,beta-epoxy sulfoxides with high enantioselectivity and diastereoselectivity dependent on the aldehyde. The mechanism of the 'model' reactions [ylide substituted with Me S(O) or Ph S(O) with MeCHO or PhCHO] has been studied in detail using density functional theory. (C) 2010 Elsevier Ltd. All rights reserved.
• Highly stereoselective aziridination of imines with (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide
  作者：Wanda H. Midura

  DOI：10.1016/j.tetlet.2007.03.117

  日期：2007.5

  Addition of (S)-dimethylsulfonium-(p-tolylsulfinyl)methylide to N-tosyl imines afforded the corresponding sulfinyl aziridines with full enantio- and diastereoselectivity. The chiral sulfinyl substituent was removed without ring opening leading to enantiopure 2-substituted aziridines. (C) 2007 Elsevier Ltd. All rights reserved.