S-methyl-N-methoxycarbonyl-S-phenylsulfilimine

• 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-methyl-N-methoxycarbonyl-S-phenylsulfilimine
• 英文别名: methyl N-[methyl(phenyl)-λ4-sulfanylidene]carbamate
• 化学式: C₉H₁₁NO₂S
• 分子量: 197.258
• InChiKey: IHRDFVYDRSALOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  茴香硫醚 、 叠氮基甲酸甲酯 在 C₆₁H₄₄N₂O₃Ru 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以21%的产率得到S-methyl-N-methoxycarbonyl-S-phenylsulfilimine
  参考文献：
  名称：

  Method of producing optically active sulfimide compounds

  摘要：

  通过使用指定的Ru(salen)(CO)复合物作为催化剂，将指定的烷基芳基砜化合物暴露于具有易于消除基团的指定叠氮化合物的不对称砜化反应中，可以制备出一种具有光学活性的砜亚胺化合物。

  公开号：

  EP1452523A3

文献信息

• Efficient nitrogen transfer from aldehyde-derived N-acyloxaziridines
  作者：Alan Armstrong、Ian D. Edmonds、Martin E. Swarbrick

  DOI：10.1016/s0040-4039(03)01200-0

  日期：2003.7

  The effect of solvent polarity on the reaction of 3-aryl-N-carboxamido- and 3-aryl-N-alkoxycarbonyl oxaziridines has been studied and an efficient procedure for high yielding sulfimidation developed by use of polar solvents. The first examples of asymmetric sulfimidation using novel chiral oxaziridines have been carried out with low diastereoselectivity (up to 30% de). (C) 2003 Elsevier Science Ltd. All rights reserved.
• N-Alkyloxycarbonyl-3-aryloxaziridines: Their Preparation, Structure, and Utilization As Electrophilic Amination Reagents
  作者：Joëlle Vidal、Stéphanie Damestoy、Laure Guy、Jean-Christophe Hannachi、André Aubry、Andreé Collet、André Aubry

  DOI：10.1002/chem.19970031019

  日期：1997.10

  AbstractThis paper reports the synthesis of a series of N‐protected oxaziridines (N‐Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N‐alkoxycar‐bonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N‐protected fragment to primary and secondary amines to give protected hydrazines in fair to excellent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N‐protected α‐hydrazino acids. Enolates are C‐aminated to give N‐protected α‐amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.
• Method of producing optically active sulfimide compounds
  申请人：KYUSHU UNIVERSITY

  公开号：EP1452523A3

  公开（公告）日：2004-09-29

  An optically active sulfimide compound is produced by using a specified Ru(salen)(CO) complex as a catalyst and subjecting a specified alkyl aryl sulfide compound to an asymmetric sulfimidation with a specified azide compound having an easily eliminating group.

  通过使用指定的Ru(salen)(CO)复合物作为催化剂，将指定的烷基芳基砜化合物暴露于具有易于消除基团的指定叠氮化合物的不对称砜化反应中，可以制备出一种具有光学活性的砜亚胺化合物。