3-phenylamino-2-[2'-(5,5-dimethyl-1,3,2-dioxaphosphorinanyl)]thiolane 1-oxide | 1158631-47-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-phenylamino-2-[2'-(5,5-dimethyl-1,3,2-dioxaphosphorinanyl)]thiolane 1-oxide
• 英文别名: (1S,2R,3R)-2-(5,5-dimethyl-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl)-1-oxo-N-phenylthiolan-3-amine；(1S,2R,3R)-2-(5,5-dimethyl-2-oxo-1,3,2λ5-dioxaphosphinan-2-yl)-1-oxo-N-phenylthiolan-3-amine
• CAS: 1158631-47-0
• 化学式: C₁₅H₂₂NO₄PS
• 分子量: 343.384
• InChiKey: NXGUUUILBNJBRD-SOHPYSCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯胺 、 2-[2'-(5,5-dimethyl-1,3,2-dioxaphosphorinano)]-2,3-didehydrothiolane 1-oxide 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以92%的产率得到3-phenylamino-2-[2'-(5,5-dimethyl-1,3,2-dioxaphosphorinanyl)]thiolane 1-oxide
  参考文献：
  名称：

  Diastereoselective Michael additions to α,β-unsaturated α-sulfinyl phosphonates in the thiolane series

  摘要：

  A chiral racemic 2-phosphono-2,3-didehydrothiolane sulfoxide was used as a Michael acceptor in the reactions with several nucleophiles, in particular thiols. In most cases the reactions were fully diastereoselective. The relative configuration of the resulting adducts was determined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.098

文献信息

• Michael addition to a chiral non-racemic 2-phosphono-2,3-didehydrothiolane S-oxide
  作者：Mihaela Gulea、Małgorzata Kwiatkowska、Piotr Łyżwa、Remi Legay、Annie-Claude Gaumont、Piotr Kiełbasiński

  DOI：10.1016/j.tetasy.2008.12.034

  日期：2009.2

  The Michael addition of selected sulfur and nitrogen nucleophiles to a chiral non-racemic 2-phosphono2,3-didehydrothiolane S-oxide is fully diastereoselective. The enantiomeric excesses of the adducts obtained could be determined by P-31 NMR spectroscopy using (R)-(+)-tert-butyl(phenyl)phosphinothioic acid as a chiral solvating agent. The addition of thiophenol was monitored by P-31 NMR spectroscopy which made it possible to observe the formation and evolution of the kinetic and thermodynamic adducts in the reaction mixture. The structures of both enantiomeric thiophenol adducts have been determined by X-ray analysis. (C) 2009 Elsevier Ltd. All rights reserved.
• Diastereoselective Michael additions to α,β-unsaturated α-sulfinyl phosphonates in the thiolane series
  作者：Piotr Łyżwa、Aleksandra Jankowiak、Małgorzata Kwiatkowska、Marian Mikołajczyk、Piotr Kiełbasiński、Alexander Betz、Paul-Alain Jaffres、Annie-Claude Gaumont、Mihaela Gulea

  DOI：10.1016/j.tetlet.2006.11.098

  日期：2007.1

  A chiral racemic 2-phosphono-2,3-didehydrothiolane sulfoxide was used as a Michael acceptor in the reactions with several nucleophiles, in particular thiols. In most cases the reactions were fully diastereoselective. The relative configuration of the resulting adducts was determined. (c) 2006 Elsevier Ltd. All rights reserved.