(S)-3,5-dihydroxy-1-phenylpentan-1-one | 1005327-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3,5-dihydroxy-1-phenylpentan-1-one
• 英文别名: (3S)-3,5-dihydroxy-1-phenylpentan-1-one
• CAS: 1005327-11-6
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: NTOWTGKSCSUJBM-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-5-hydroxy-1-phenylpent-2-en-1-one 在 quinine-based catalyst 4 A molecular sieve 、 苯硼酸 、 双氧水 、 sodium carbonate 作用下， 以 甲苯 、 乙酸乙酯 为溶剂， 反应 12.25h， 生成 (3R)-3,5-dihydroxy-1-phenylpentan-1-one 、 (S)-3,5-dihydroxy-1-phenylpentan-1-one
  参考文献：
  名称：

  Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons

  摘要：

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.

  DOI：

  10.1021/ja076802c

文献信息

• Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons
  作者：De Run Li、Andiappan Murugan、J. R. Falck

  DOI：10.1021/ja076802c

  日期：2008.1.1

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.