(2R,3R,E)-3-ethylpentan-3-yl 3-hydroxy-2-methyl-5-phenylpent-4-enoate | 1448551-59-4

• 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,3R,E)-3-ethylpentan-3-yl 3-hydroxy-2-methyl-5-phenylpent-4-enoate
• CAS: 1448551-59-4
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: VBIGYTFJGKBFBA-RCKIBTJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-Ethylpentan-3-yl prop-2-enoate 以 乙醚 为溶剂， 反应 20.0h， 生成 (2R,3R,E)-3-ethylpentan-3-yl 3-hydroxy-2-methyl-5-phenylpent-4-enoate 、 (2S,3S,E)-3-ethylpentan-3-yl 3-hydroxy-2-methyl-5-phenylpent-4-enoate 、 (2R*,3S*,E)-3-ethylpentan-3-yl 3-hydroxy-2-methyl-5-phenylpent-4-enoate
  参考文献：
  名称：

  (Diisopinocampheyl)borane-Mediated Reductive Aldol Reactions of Acrylate Esters: Enantioselective Synthesis of Anti-Aldols

  摘要：

  The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-alpha-methyl-beta-hydroxy esters 9 or 10 with excellent diastereo- (up to >= 20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.

  DOI：

  10.1021/ol401679g