(2R,3S)-4-diphenylphosphinoyl-2,3-epoxybutan-1-ol | 145653-12-9

• 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: (2R,3S)-4-diphenylphosphinoyl-2,3-epoxybutan-1-ol
• 英文别名: [(2R,3S)-3-(diphenylphosphorylmethyl)oxiran-2-yl]methanol
• CAS: 145653-12-9
• 化学式: C₁₆H₁₇O₃P
• 分子量: 288.283
• InChiKey: BYGXDMOFIDHFEB-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-4-diphenylphosphinoylbut-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R)-4-diphenylphosphinoyl-2,3-epoxybutan-1-ol 、 (2R,3S)-4-diphenylphosphinoyl-2,3-epoxybutan-1-ol
  参考文献：
  名称：

  Asymmetric epoxidations and kinetic resolutions of δ-hydroxy allylic phosphine oxides

  摘要：

  Delta-Hydroxy allylic phosphine oxides 5 undergo asymmetric epoxidation to yield epoxy alcohols 6 with high enantio- and diastereoselectivity. Kinetic resolutions are also successful, even with a chiral centre remote from the allylic hydroxyl, if that chiral centre bears a diphenylphosphinoyl group. The diphenylphosphinoyl group then exerts a novel anti-directing effect on the epoxidation.

  DOI：

  10.1016/s0040-4039(00)60928-0

文献信息

• Asymmetric epoxidations and kinetic resolutions of δ-hydroxy allylic phosphine oxides
  作者：Jonathan Clayden、Eric W. Collington、Stuart Warren

  DOI：10.1016/s0040-4039(00)60928-0

  日期：1992.11

  Delta-Hydroxy allylic phosphine oxides 5 undergo asymmetric epoxidation to yield epoxy alcohols 6 with high enantio- and diastereoselectivity. Kinetic resolutions are also successful, even with a chiral centre remote from the allylic hydroxyl, if that chiral centre bears a diphenylphosphinoyl group. The diphenylphosphinoyl group then exerts a novel anti-directing effect on the epoxidation.
• Clayden, Jonathan; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1994, # 19, p. 2811 - 2824
  作者：Clayden, Jonathan、Warren, Stuart

  DOI：——

  日期：——