O,O-dimenthyl thiophosphite | 632366-45-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: O,O-dimenthyl thiophosphite
• 英文别名: bis[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy]-sulfidophosphanium
• CAS: 632366-45-1
• 化学式: C₂₀H₃₉O₂PS
• 分子量: 374.568
• InChiKey: GEJGHJHLSNGHPT-XRNRSJMDSA-N

物化性质

• 沸点：
  425.3±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  19.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O,O-dimenthyl thiophosphite 在 三乙基硼 、 间氯过氧苯甲酸 作用下， 以 环己烷 为溶剂， 生成 Octyl-phosphonic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester
  参考文献：
  名称：

  Radical addition reactions of chiral phosphorus hydrides

  摘要：

  Intermolecular radical addition of a (1R,2R,3S,5R)-(-)-pinanediol-derived thiophosphite leads to the diastereoselective formation of organophosphorus adducts. Addition of the intermediate phosphonothioyl radical to electron-rich alkenes or alkynes occurs with retention of configuration at phosphorus. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.04.001
• 作为产物：
  描述：

  hydrogen di[(1R,2S,5R)-menthyl] phosphite 在 劳森试剂 作用下， 以95%的产率得到O,O-dimenthyl thiophosphite
  参考文献：
  名称：

  Radical addition reactions of chiral phosphorus hydrides

  摘要：

  Intermolecular radical addition of a (1R,2R,3S,5R)-(-)-pinanediol-derived thiophosphite leads to the diastereoselective formation of organophosphorus adducts. Addition of the intermediate phosphonothioyl radical to electron-rich alkenes or alkynes occurs with retention of configuration at phosphorus. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.04.001

文献信息

• Enantiomerically pure disulfides: key compounds in the kinetic resolution of chiral PIII-derivatives with stereogenic phosphorus
  作者：Wieslawa Perlikowska、Maryse Gouygou、Marian Mikolajczyk、Jean-Claude Daran

  DOI：10.1016/j.tetasy.2004.09.014

  日期：2004.11

  Enantiomerically pure disulfides were reacted with various chiral P-III-derivatives with stereogenic phosphorus such as tertiary phosphines, halogenophosphines, phosphinite and phosphole under kinetic resolution conditions to afford enantiomerically enriched phosphine oxides or sulfides with ee values up to 50%. Enantiomeric excess rose to 70% under dynamic kinetic resolution-conditions in the case of tert-butylphenylchlorophosphine. (C) 2004 Elsevier Ltd. All rights reserved.