ethyl 5-oxo-2-cyano-3-phenyl-2-(3-methylbuyl)-3-hexenoate

• 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: ethyl 5-oxo-2-cyano-3-phenyl-2-(3-methylbuyl)-3-hexenoate
• 英文别名: ethyl 2-cyano-2-(3-methylbutyl)-5-oxo-3-phenylhex-3-enoate
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: AHRDJUANJWIMOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氰基-5-甲基己酸乙酯 、 4-苯基-3-丁炔-2-酮 在 三(二甲胺基)膦 作用下， 以 乙腈 为溶剂， 以77%的产率得到ethyl 5-oxo-2-cyano-3-phenyl-2-(3-methylbuyl)-3-hexenoate
  参考文献：
  名称：

  Phosphoramidites Are Efficient, Green Organocatalysts for the Michael Reaction. Mechanistic Insights into the Phosphorus-Catalyzed Michael Reaction of Alkynones and Implications for Asymmetric Catalysis

  摘要：

  Hexamethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, (x-cyano, esters, beta-keto esters, and nitro compounds. The relatively nontoxic, easily hydrolyzed HMPT catalyzes the Michael reaction within seconds at room temperature in the absence of a solvent, and the reaction is worked up simply by removing the catalyst in vacuo. The Michael reactions of alkynones, unlike those of alkenones, are shown to be irreversible. The implications for asymmetric catalysis are discussed.

  DOI：

  10.1021/jo026425g

文献信息

• Phosphoramidites Are Efficient, Green Organocatalysts for the Michael Reaction. Mechanistic Insights into the Phosphorus-Catalyzed Michael Reaction of Alkynones and Implications for Asymmetric Catalysis
  作者：Robert B. Grossman、Sébastien Comesse、Ravindra M. Rasne、Kazuyuki Hattori、Matthew N. Delong

  DOI：10.1021/jo026425g

  日期：2003.2.1

  Hexamethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, (x-cyano, esters, beta-keto esters, and nitro compounds. The relatively nontoxic, easily hydrolyzed HMPT catalyzes the Michael reaction within seconds at room temperature in the absence of a solvent, and the reaction is worked up simply by removing the catalyst in vacuo. The Michael reactions of alkynones, unlike those of alkenones, are shown to be irreversible. The implications for asymmetric catalysis are discussed.