2-(3-Acetyl-4-hydroxy-naphthalen-1-yl)-3-(triphenyl-λ5-phosphanylidene)-succinic acid diethyl ester | 478622-11-6

• 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: 2-(3-Acetyl-4-hydroxy-naphthalen-1-yl)-3-(triphenyl-λ5-phosphanylidene)-succinic acid diethyl ester
• 英文别名: 2-(3-Acetyl-4-hydroxy-naphthalen-1-yl)-3-(triphenyl-λ⁵-phosphanylidene)-succinic acid diethyl ester
• CAS: 478622-11-6
• 化学式: C₃₈H₃₅O₆P
• 分子量: 618.666
• InChiKey: VUUCGLZOZVNOPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  89.9
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(3-Acetyl-4-hydroxy-naphthalen-1-yl)-3-(triphenyl-λ5-phosphanylidene)-succinic acid diethyl ester 在 silica gel 作用下， 反应 0.02h， 生成 (E)-2-(3-Acetyl-4-hydroxy-naphthalen-1-yl)-but-2-enedioic acid diethyl ester
  参考文献：
  名称：

  Microwave Induced Conversion of Dialkyl 2-(3-Acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene)Butanedioates to Dialkyl 2-(3-Acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in the Presence of Silica Gel Powder in Solvent-Free Conditions

  摘要：

  Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 1-hydroxy-2-acetonaphthone leads to vinyltriphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with conjugate base to produce dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates. Microwave was found to catalyze conversion of dialkyl 2-(3-acety1-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates to dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in the presence of silica gel powder in solvent-free conditions.

  DOI：

  10.1080/713744559
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 、 三苯基膦 、 丁炔二酸二乙酯 以 二氯甲烷 为溶剂， 生成 2-(3-Acetyl-4-hydroxy-naphthalen-1-yl)-3-(triphenyl-λ5-phosphanylidene)-succinic acid diethyl ester
  参考文献：
  名称：

  Silica Gel Catalyzed Stereoselective Conversion of Dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates to Dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in Solvent-Free Conditions

  摘要：

  Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 1-hydroxy-2-acetonaphthone leads to vinyltriphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with conjugate base to produce dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates. Silica gel was found to catalyze conversion of dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates to dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in solvent-free conditions at 90degreesC in fairly good yields.

  DOI：

  10.1080/10426500210658