5-Benzyl-1,2,3,4,5-pentakis(methoxycarbonyl)cyclopentadiene | 114121-72-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-Benzyl-1,2,3,4,5-pentakis(methoxycarbonyl)cyclopentadiene
• 英文别名: Pentamethyl 5-benzylcyclopenta-1,3-diene-1,2,3,4,5-pentacarboxylate
• CAS: 114121-72-1
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: CKRDEERYVUPHSK-UHFFFAOYSA-N

物化性质

• 熔点：
  105-107 °C
• 沸点：
  542.0±50.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-Benzyl-1,2,3,4,5-pentakis(methoxycarbonyl)cyclopentadiene 以 氘代甲醇 为溶剂， 反应 3.0h， 生成 4-Benzyl-1,2,3,5,5-pentakis(methoxycarbonyl)cyclopentadiene 、 3-Benzyl-1,2,4,5,5-pentakis(methoxycarbonyl)cyclopentadiene
  参考文献：
  名称：

  Thermal rearrangements and reactions of 5-alkyl-1,2,3,4,5-pentakis(methoxycarbonyl)cyclopentadienes

  摘要：

  Studies of the thermal reactions of five Balkyl-1,2,3,4,5-pentakis (methoxycarbonyl)cyclopentadienes in methanol solvent are described, where the alkyl groups are benzhydryl, methoxymethyl, 1-adamantyl, p-methoxybenzyl, and benzyl. The benzyl cyclopentadiene system undergoes thermal [1,5]-sigmatropic rearrangement via methoxycarbonyl migrations while the other cyclopentadienes undergo C-alkyl bond heterolysis to ion-pair intermediates, which are scavenged by solvent. First-order rate constants for solvolysis of the methoxymethyl, 1-adamantyl, and p-methoxybenzyl systems in methanol solvent were determined and that for the benzhydryl system was estimated from a single measurement of the half-life.

  DOI：

  10.1021/jo00081a029
• 作为产物：
  描述：

  1,2,3,4,5-Pentakis(methoxycarbonyl)-5-(1,1-diphenylmethyl)cyclopentadiene 在 silver(l) oxide 作用下， 以 苯 为溶剂， 反应 4.33h， 生成 5-Benzyl-1,2,3,4,5-pentakis(methoxycarbonyl)cyclopentadiene
  参考文献：
  名称：

  Thermal rearrangements and reactions of 5-alkyl-1,2,3,4,5-pentakis(methoxycarbonyl)cyclopentadienes

  摘要：

  Studies of the thermal reactions of five Balkyl-1,2,3,4,5-pentakis (methoxycarbonyl)cyclopentadienes in methanol solvent are described, where the alkyl groups are benzhydryl, methoxymethyl, 1-adamantyl, p-methoxybenzyl, and benzyl. The benzyl cyclopentadiene system undergoes thermal [1,5]-sigmatropic rearrangement via methoxycarbonyl migrations while the other cyclopentadienes undergo C-alkyl bond heterolysis to ion-pair intermediates, which are scavenged by solvent. First-order rate constants for solvolysis of the methoxymethyl, 1-adamantyl, and p-methoxybenzyl systems in methanol solvent were determined and that for the benzhydryl system was estimated from a single measurement of the half-life.

  DOI：

  10.1021/jo00081a029

文献信息

• QIU, CHANGLONG;WU, MINYANG;ZHOU, ZHIHONG, CHEM. J. CLIN. UNIV., 8,(1987) N 8, 712-713
  作者：QIU, CHANGLONG、WU, MINYANG、ZHOU, ZHIHONG

  DOI：——

  日期：——
• Thermal rearrangements and reactions of 5-alkyl-1,2,3,4,5-pentakis(methoxycarbonyl)cyclopentadienes
  作者：Elizabeth A. Jefferson、John Warkentin

  DOI：10.1021/jo00081a029

  日期：1994.1

  Studies of the thermal reactions of five Balkyl-1,2,3,4,5-pentakis (methoxycarbonyl)cyclopentadienes in methanol solvent are described, where the alkyl groups are benzhydryl, methoxymethyl, 1-adamantyl, p-methoxybenzyl, and benzyl. The benzyl cyclopentadiene system undergoes thermal [1,5]-sigmatropic rearrangement via methoxycarbonyl migrations while the other cyclopentadienes undergo C-alkyl bond heterolysis to ion-pair intermediates, which are scavenged by solvent. First-order rate constants for solvolysis of the methoxymethyl, 1-adamantyl, and p-methoxybenzyl systems in methanol solvent were determined and that for the benzhydryl system was estimated from a single measurement of the half-life.