4-methyl-3-benzoyloxypentan-2-one

• 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: 4-methyl-3-benzoyloxypentan-2-one
• 英文别名: 3-benzoyloxy-4-methyl-pentan-2-one；3-Benzoyloxy-4-methyl-pentan-2-on；(2-Methyl-4-oxopentan-3-yl) benzoate；(2-methyl-4-oxopentan-3-yl) benzoate
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: JHOCTYPUTPORIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(tert-butyloxycarbonyl)-N-methyl-O-benzoyl-hydroxylamine 在 盐酸 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 4-methyl-3-benzoyloxypentan-2-one
  参考文献：
  名称：

  A General Method for the α-Acyloxylation of Carbonyl Compounds

  摘要：

  A simple, one-pot method for the alpha-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the alpha-functionalized product in 69-92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is reglospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.

  DOI：

  10.1021/ol052474e

文献信息

• 537. Elimination reactions. Part I. Acid-catalysed enolisation and substitution reactions of ketones
  作者：H. M. E. Cardwell、A. E. H. Kilner

  DOI：10.1039/jr9510002430

  日期：——
• A PRACTICAL PROCEDURE FOR CARBONYL a-OXIDATION: SYNTHESIS OF (2-BENZOYLOXY)-1,4-CYCLOHEXANEDIONE MONO-ETHYLENE KETAL
  作者：Jones, Teyrnon C.、Tomkinson, Nicholas C. O.、Patil, Kalyani、Wipf, Peter

  DOI：10.15227/orgsyn.084.0233

  日期：——
• A General Method for the α-Acyloxylation of Carbonyl Compounds
  作者：Cory S. Beshara、Adrian Hall、Robert L. Jenkins、Kerri L. Jones、Teyrnon C. Jones、Niall M. Killeen、Paul H. Taylor、Stephen P. Thomas、Nicholas C. O. Tomkinson

  DOI：10.1021/ol052474e

  日期：2005.12.1

  A simple, one-pot method for the alpha-acyloxylation of carbonyl compounds that proceeds at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provides the alpha-functionalized product in 69-92% isolated yield. The transformation is tolerant of a wide range of functional groups and, significantly, is reglospecific in the discrimination of secondary over primary centers in the case of nonsymmetrical substrates.