4-(4-methoxyphenyl)nonan-5-one | 1268834-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)nonan-5-one
• 英文别名: 4-(4-Methoxyphenyl)nonan-5-one
• CAS: 1268834-06-5
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: YXZMTORWBBIGGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5-壬酮 、 4-氯苯甲醚 在 NHC-Pd(II)-Im 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以83%的产率得到4-(4-methoxyphenyl)nonan-5-one
  参考文献：
  名称：

  N -Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation of symmetric dialkyl ketones with aryl chlorides

  摘要：

  N-Heterocyclic carbene-palladium(II)-1-methylimidazole [NHC-Pd(II)-Im] complex 1 showed efficient catalytic activity toward alpha-arylation of symmetric dialkyl ketones under mild conditions. It was found that the ratio of aryl chlorides and ketones drastically affected the reaction. When the ratio of aryl chlorides and ketones was 1:2, mono-arylated products can be obtained in good to high yields as the sole; while that of aryl chlorides and ketones was changed to 1:0.7, di- and mono-arylated products were obtained in good to high total yields at the same time, with the former as the major. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.07.061

文献信息

• Nucleophilic α-Arylation and α-Alkylation of Ketones by Polarity Inversion of N-Alkoxyenamines: Entry to the Umpolung Reaction at the α-Carbon Position of Carbonyl Compounds
  作者：Tetsuya Miyoshi、Takayuki Miyakawa、Masafumi Ueda、Okiko Miyata

  DOI：10.1002/anie.201004374

  日期：2011.1.24

  N‐alkoxyenamines from ketones has led to an efficient umpolung reaction. The alkylation of N‐alkoxyenamines with trialkylaluminum compounds proceeded smoothly and gave α‐alkylated ketones (see scheme). This reaction offers a simple transformation of ketones into α‐substituted ketones without the need to isolate enamines and intermediary imines.

  烯胺化学的一个新方面：由酮形成N烷氧基烯胺导致了有效的umpolung反应。的烷基化Ñ -alkoxyenamines与三烷基铝化合物顺利进行，给α -烷基化的酮（参见方案）。该反应无需分离烯胺和中间体亚胺，即可将酮简单地转化为α-取代的酮。