tert-butyl (2S,3R,4E)-3-hydroxy-2-methyl-5-phenylpent-4-enoate | 127422-15-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: tert-butyl (2S,3R,4E)-3-hydroxy-2-methyl-5-phenylpent-4-enoate
• 英文别名: (2S,3S)-(E)-tert-butyl 3-hydroxy-2-methyl-5-phenylpent-4-enoate；tert-butyl (2R,3S,4E)-3-hydroxy-2-methyl-5-phenylpent-4-enoate
• CAS: 127422-15-5；127422-16-6
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: GTOHDUXJKMINIV-DISFZNMFSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  200 °C(Press: 0.01 Torr)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  丙烯酸叔丁酯 以 乙醚 为溶剂， 反应 20.0h， 生成 (2S,3S)-(E)-tert-butyl 3-hydroxy-2-methyl-5-phenylpent-4-enoate 、 tert-butyl(E,2R,3R)-3-hydroxy-2-methyl-5-phenylpent-4-enoate 、 tert-butyl (2S,3R,4E)-3-hydroxy-2-methyl-5-phenylpent-4-enoate 、 tert-butyl (2S,3R,4E)-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

文献信息

• High Performance of Rh(Phebox) Catalysts in Asymmetric Reductive Aldol Reaction:  High Anti-Selectivity
  作者：Hisao Nishiyama、Takushi Shiomi、Yasunori Tsuchiya、Isamu Matsuda

  DOI：10.1021/ja050698m

  日期：2005.5.1

  Chiral rhodium(bisoxazolinylphenyl) complexes (1 mol %) efficiently catalyze the asymmetric reductive aldol reaction of aldehydes and alpha,beta-unsaturated esters at 50 degrees C for ca. 0.5-1.0 h with several hydrosilanes to give the corresponding beta-hydroxypropionates with extremely high anti-selectivity (up to 98%) and enantioselectivity (up to 96% ee). The stereochemical outcome is likely due

  手性铑(双恶唑啉基苯基) 配合物 (1 mol %) 有效地催化醛和 α，β-不饱和酯在 50 摄氏度的不对称还原醛醇反应约。使用几种氢硅烷反应 0.5-1.0 小时，得到具有极高抗选择性（高达 98%）和对映选择性（高达 96% ee）的相应 β-羟基丙酸酯。立体化学结果可能是由于涉及铑-(E)-烯醇化物的椅子状循环过渡态。
• Versatile chiral reagent for the highly enantioselective synthesis of either anti or syn ester aldols
  作者：E. J. Corey、Sung Soo Kim

  DOI：10.1021/ja00168a062

  日期：1990.6