(1S,2R)-3-(diphenylphosphinoyl)-1-phenylpropane-1,2-diol | 165611-42-7

• 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: (1S,2R)-3-(diphenylphosphinoyl)-1-phenylpropane-1,2-diol
• 英文别名: (1S,2R)-3-diphenylphosphoryl-1-phenylpropane-1,2-diol
• CAS: 165611-42-7
• 化学式: C₂₁H₂₁O₃P
• 分子量: 352.37
• InChiKey: ODINLGQLVMAGGF-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (1S,2R)-3-(diphenylphosphinoyl)-1-phenylpropane-1,2-diol 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以84%的产率得到(4S,5R)-2,2-dimethyl-4-phenyl-5-(diphenylphosphinoylmethyl)-1,3-dioxolane
  参考文献：
  名称：

  A practical synthesis of syn- and anti-α,β-dihydroxyphosphinates via diastereoselective reduction of α-phosphinoyl ketones

  摘要：

  Reduction of (3-keto-diphenylphosphine oxide (S)-4 derived from (S)-mandelic acid with NaBH4 in methanol at -78 degrees C gave the anti-3-diphenylphosphinoyl-1,2-diol 6, whereas the reduction of (S)-4 with Zn(BH4)(2) in THF at -78 degrees C afforded the syn-1,2-diol 5, both in high yield and excellent diastercoselectivity. This procedure represents a new approach to the diastereoselective synthesis of diphenylphosphinoyl diols and an example of highly diastereoselective 1,2-induction. A theoretical model to explain the direction and degree of asymmetric induction is proposed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.12.016
• 作为产物：
  描述：

  (1S,2R)-1-[(tert-butyldimethylsilyl)oxy]-3-(diphenylphosphinoyl)-1-phenylpropan-2-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到(1S,2R)-3-(diphenylphosphinoyl)-1-phenylpropane-1,2-diol
  参考文献：
  名称：

  A practical synthesis of syn- and anti-α,β-dihydroxyphosphinates via diastereoselective reduction of α-phosphinoyl ketones

  摘要：

  Reduction of (3-keto-diphenylphosphine oxide (S)-4 derived from (S)-mandelic acid with NaBH4 in methanol at -78 degrees C gave the anti-3-diphenylphosphinoyl-1,2-diol 6, whereas the reduction of (S)-4 with Zn(BH4)(2) in THF at -78 degrees C afforded the syn-1,2-diol 5, both in high yield and excellent diastercoselectivity. This procedure represents a new approach to the diastereoselective synthesis of diphenylphosphinoyl diols and an example of highly diastereoselective 1,2-induction. A theoretical model to explain the direction and degree of asymmetric induction is proposed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.12.016

文献信息

• Asymmetric dihydroxylations of allylic phosphine oxides
  作者：Adam Nelson、Peter O'Brien、Stuart Warren

  DOI：10.1016/0040-4039(95)00335-a

  日期：1995.4

  Allylic phosphine oxides 6 undergo asymmetric dihydroxylation to yield 1,2 diols 9. The enantioselectivity of these reactions depends critically on the class and quantity of chiral ligand used. A model to explain the sense and degree of asymmetric induction is proposed.
• Nelson, Adam; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1997, # 17, p. 2645 - 2657
  作者：Nelson, Adam、Warren, Stuart

  DOI：——

  日期：——
• A practical synthesis of syn- and anti-α,β-dihydroxyphosphinates via diastereoselective reduction of α-phosphinoyl ketones
  作者：Haydée Rojas-Cabrera、Julio M. Hernández-Pérez、Minhhuy Hô、Eugenio Hernández-Fernández、Mario Ordóñez

  DOI：10.1016/j.tetasy.2007.12.016

  日期：2008.2

  Reduction of (3-keto-diphenylphosphine oxide (S)-4 derived from (S)-mandelic acid with NaBH4 in methanol at -78 degrees C gave the anti-3-diphenylphosphinoyl-1,2-diol 6, whereas the reduction of (S)-4 with Zn(BH4)(2) in THF at -78 degrees C afforded the syn-1,2-diol 5, both in high yield and excellent diastercoselectivity. This procedure represents a new approach to the diastereoselective synthesis of diphenylphosphinoyl diols and an example of highly diastereoselective 1,2-induction. A theoretical model to explain the direction and degree of asymmetric induction is proposed. (C) 2008 Elsevier Ltd. All rights reserved.