methyl 2-[2-(2-naphthyl)-2-oxoethyl]-3-(1,1,1-triphenyl-λ⁵-phosphanylidene)succinate | 1156461-21-0

• 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: methyl 2-[2-(2-naphthyl)-2-oxoethyl]-3-(1,1,1-triphenyl-λ⁵-phosphanylidene)succinate
• 英文别名: Dimethyl 2-(2-naphthalen-2-yl-2-oxoethyl)-3-(triphenyl-lambda5-phosphanylidene)butanedioate；dimethyl 2-(2-naphthalen-2-yl-2-oxoethyl)-3-(triphenyl-λ5-phosphanylidene)butanedioate
• CAS: 1156461-21-0
• 化学式: C₃₆H₃₁O₅P
• 分子量: 574.613
• InChiKey: AZPHVUYFTGGUTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 basic alumina powder 作用下， 反应 2.0h， 生成 methyl 2-[2-(2-naphthyl)-2-oxoethyl]-3-(1,1,1-triphenyl-λ⁵-phosphanylidene)succinate
  参考文献：
  名称：

  Synthesis of Sterically Congested Stabilized Phosphorus Ylides from Acetylenic Esters, 4,4,4-Trifluoro-1-(2naphthyl)-1,3-butanedione, and Triphenylphosphine

  摘要：

  Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione leads to vinyltriphenylphosphonium salts, which undergo Michael addition reaction with conjugate base to produce corresponding sterically congested fluorine-containing phosphorus ylides. Basic alumina powder was found to catalyze conversion of the sterically congested fluorine-containing phosphorus ylides to dialkyl 2-[2-(2-naphthyl)-2-oxoethyl]-3-(1,1,1-triphenyl-lambda(5)-phosphanylidene)succinates in solvent-free conditions under microwave (0.9 KW, 3 min) and thermal (25 degrees C, 120 min.) conditions.

  DOI：

  10.1080/10426500701693420