3,4-dihydroxy-4-methyl-1-phenyl-1-pentanone | 137277-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihydroxy-4-methyl-1-phenyl-1-pentanone
• 英文别名: 3,4-dihydroxy-4-methyl-1-phenylpentan-1-one
• CAS: 137277-98-6
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: PAYRKEMXCDWONN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  4-methyl-1-phenyl-3,4-epoxy-1-pentanone 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到3,4-dihydroxy-4-methyl-1-phenyl-1-pentanone
  参考文献：
  名称：

  Synthesis of a substituted 6,8-dioxabicyclo[3.2.1]octane

  摘要：

  DOI：

  10.1007/bf00474007

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.
• Synthesis of a substituted 6,8-dioxabicyclo[3.2.1]octane
  作者：P. U. Posas、L. S. Novikov、V. A. Mezhentsev

  DOI：10.1007/bf00474007

  日期：1991.5