(S(S),S)-diethyl 1-((S)-tert-butylsulfinylamino)-2,2,2-trifluoroethylphosphonate | 1353220-88-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (S(S),S)-diethyl 1-((S)-tert-butylsulfinylamino)-2,2,2-trifluoroethylphosphonate
• 英文别名: (S)-N-[(1S)-1-diethoxyphosphoryl-2,2,2-trifluoroethyl]-2-methylpropane-2-sulfinamide
• CAS: 1353220-88-8
• 化学式: C₁₀H₂₁F₃NO₄PS
• 分子量: 339.316
• InChiKey: ZMGFSGOEQHTGHH-FHZGZLOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S(S),S)-diethyl 1-((S)-tert-butylsulfinylamino)-2,2,2-trifluoroethylphosphonate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以89%的产率得到O,O-diethyl (S)-(1-amino-2,2,2-trifluoroethyl)phosphonate
  参考文献：
  名称：

  Asymmetric synthesis of phosphonotrifluoroalanine and its derivatives using N-tert-butanesulfinyl imine derived from fluoral

  摘要：

  Addition of dialkyl phosphites to (S)-N-tert-butanesulfinyl imine derived from fluoral afforded, under mild conditions, the corresponding N-tert-butanesulfinyl alpha-aminophosphonates in moderate to high yields and diastereoselectivity. The major diastereomers of N-tert-butanesulfinyl alpha-arninophosphonates of (S-s,S) configuration were isolated, and after partial or complete deprotection, converted into enantiomerically pure phosphonotrifluoroalanine and its dialkyl esters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.096
• 作为产物：
  描述：

  (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine 、 亚磷酸二乙酯 在 三甲基氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以54%的产率得到(S(S),S)-diethyl 1-((S)-tert-butylsulfinylamino)-2,2,2-trifluoroethylphosphonate
  参考文献：
  名称：

  Asymmetric synthesis of phosphonotrifluoroalanine and its derivatives using N-tert-butanesulfinyl imine derived from fluoral

  摘要：

  Addition of dialkyl phosphites to (S)-N-tert-butanesulfinyl imine derived from fluoral afforded, under mild conditions, the corresponding N-tert-butanesulfinyl alpha-aminophosphonates in moderate to high yields and diastereoselectivity. The major diastereomers of N-tert-butanesulfinyl alpha-arninophosphonates of (S-s,S) configuration were isolated, and after partial or complete deprotection, converted into enantiomerically pure phosphonotrifluoroalanine and its dialkyl esters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.096

文献信息

• Asymmetric synthesis of phosphonotrifluoroalanine and its derivatives using N-tert-butanesulfinyl imine derived from fluoral
  作者：Gerd-Volker Röschenthaler、Valery P. Kukhar、Irine B. Kulik、Michael Yu. Belik、Alexander E. Sorochinsky、Eduard B. Rusanov、Vadim A. Soloshonok

  DOI：10.1016/j.tetlet.2011.11.096

  日期：2012.2

  Addition of dialkyl phosphites to (S)-N-tert-butanesulfinyl imine derived from fluoral afforded, under mild conditions, the corresponding N-tert-butanesulfinyl alpha-aminophosphonates in moderate to high yields and diastereoselectivity. The major diastereomers of N-tert-butanesulfinyl alpha-arninophosphonates of (S-s,S) configuration were isolated, and after partial or complete deprotection, converted into enantiomerically pure phosphonotrifluoroalanine and its dialkyl esters. (C) 2011 Elsevier Ltd. All rights reserved.