3-(4-methoxyphenyl)-4,4-dimethylcyclohexanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxyphenyl)-4,4-dimethylcyclohexanone
• 英文别名: 3-(4-Methoxyphenyl)-4,4-dimethylcyclohexan-1-one
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: PABAOQQJBSPENO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4-二甲基-2-环己基-1-酮 、 对甲氧基苯硼酸酐 在 sodium nitrate 、 Pd(MeCN)₄(OTf)₂ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以81%的产率得到3-(4-methoxyphenyl)-4,4-dimethylcyclohexanone
  参考文献：
  名称：

  Mild and Ligand-Free Pd(II)-Catalyzed Conjugate Additions to Hindered γ-Substituted Cyclohexenones

  摘要：

  Ligand-free cationic Pd(II) catalyst with NaNO3 as an additive is a highly active catalytic system for conjugate additions to sterically hindered gamma-substituted cyclohexenones. More challenging gamma gamma- and beta gamma-substrates also react well to produce products with quaternary centers in good dr. The conjugate additions occur in a diastereoselective fashion under mild, practical and air-stable conditions, using readily available commercial reagents.

  DOI：

  10.1021/ol300794a

文献信息

• Osmium-Promoted Electrophilic Substitution of Anisoles:  A Versatile New Method for the Incorporation of Carbon Substituents
  作者：Stanley P. Kolis、Michael E. Kopach、Ronggang Liu、W. Dean Harman

  DOI：10.1021/jo961983e

  日期：1997.1.1

  A structurally and electronically diverse set of anisoles are dihapto-coordinated to the pi-base pentaammineosmium(II) and treated with a variety of carbon electrophiles (e.g. Michael accepters, acetals). After deprotonation of a 4H-anisolium intermediate with a tertiary amine base, C(4)-substituted anisole complexes are isolated. The functionalized arenes are removed from the metal center either by mild heating or treatment with an oxidant (e.g. AgOTf, DDQ, CAN). The resulting substituted anisoles are isolated with yields ranging from 55-95%.
• Mild and Ligand-Free Pd(II)-Catalyzed Conjugate Additions to Hindered γ-Substituted Cyclohexenones
  作者：James A. Jordan-Hore、James N. Sanderson、Ai-Lan Lee

  DOI：10.1021/ol300794a

  日期：2012.5.18

  Ligand-free cationic Pd(II) catalyst with NaNO3 as an additive is a highly active catalytic system for conjugate additions to sterically hindered gamma-substituted cyclohexenones. More challenging gamma gamma- and beta gamma-substrates also react well to produce products with quaternary centers in good dr. The conjugate additions occur in a diastereoselective fashion under mild, practical and air-stable conditions, using readily available commercial reagents.