(S)-1-[(tert-butyldimethylsilyl)oxy]-3-(diphenylphosphinoyl)-1-phenylpropan-2-one | 1010708-42-5

• 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)-1-[(tert-butyldimethylsilyl)oxy]-3-(diphenylphosphinoyl)-1-phenylpropan-2-one
• 英文别名: (1S)-1-[tert-butyl(dimethyl)silyl]oxy-3-diphenylphosphoryl-1-phenylpropan-2-one
• CAS: 1010708-42-5
• 化学式: C₂₇H₃₃O₃PSi
• 分子量: 464.616
• InChiKey: LSORKMIBMJFMDR-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-[(tert-butyldimethylsilyl)oxy]-3-(diphenylphosphinoyl)-1-phenylpropan-2-one 在 zinc(II) tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以90%的产率得到(1S,2R)-1-[(tert-butyldimethylsilyl)oxy]-3-(diphenylphosphinoyl)-1-phenylpropan-2-ol
  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：

  苯乙酸,a-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-,甲基酯,(S)- 、 甲基二苯基氧化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.0h， 以75%的产率得到(S)-1-[(tert-butyldimethylsilyl)oxy]-3-(diphenylphosphinoyl)-1-phenylpropan-2-one
  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

• 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.