5-norbornene-1,3-dicarboximido indole-3-acetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-norbornene-1,3-dicarboximido indole-3-acetate
• 英文别名: (3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl) 2-(1H-indol-3-yl)acetate
• 化学式: C₁₉H₁₆N₂O₄
• 分子量: 336.347
• InChiKey: PSJKDWIQXFFFSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-吲哚乙酸 、 N-羟基-5-降冰片烯-2,3-二甲酰亚胺 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 5-norbornene-1,3-dicarboximido indole-3-acetate
  参考文献：
  名称：

  Aminolysis of activated esters of indole-3-acetic acid in acetonitrile

  摘要：

  Seven activated esters of indole-3-acetic acid (IAA) [4-oxo-1,2,3-benzotriazin-3-yl indole-3-acetate (IAA-3HBO), succinimido indole-3-acetate (IAA-NHS), 5-norbornene-1,3-dicarboximido indole-3-acetate (IAA-NHND), phthalimido indole-3-acetate (IAA-NHP), naphthalimido indole-3-acetate (IAA-NHN), 4-nitrophenyl indole-3-acetate (IAA-4NP), 8-quinolyl indole-3-acetate (IAA-8HQ)] were prepared and characterized. Their kinetics of aminolysis with butylamine, piperidine, and pyrrolidine in acetonitrile were investigated. In general, the observed pseudo-first-order rate constants, k(obs), fit the two-term rate equation k(obs) = k1[amine] + k2[amine]2. For the aminolysis of six of the esters with piperidine there was no measurable k2 term. The 8-hydroxyquinoline ester and N-hydroxynaphthalimide ester of indole-3-acetic acid had no measurable k2 term for aminolysis with either pyrrolidine or piperidine. In general, the reactivity of the esters increased with increasing acidity of the conjugate acid of the nucleofuge and with increasing base strength of the nucleophilic amine. The IAA ester of NHP was observed to be ca. 100-fold more reactive than the IAA ester of 4NP although the pK(a)'s of the leaving groups are nearly the same. In all cases low activation energies were observed.

  DOI：

  10.1021/jo00055a031

文献信息

• Aminolysis of activated esters of indole-3-acetic acid in acetonitrile
  作者：Michael J. Pfeiffer、Samir B. Hanna

  DOI：10.1021/jo00055a031

  日期：1993.1

  Seven activated esters of indole-3-acetic acid (IAA) [4-oxo-1,2,3-benzotriazin-3-yl indole-3-acetate (IAA-3HBO), succinimido indole-3-acetate (IAA-NHS), 5-norbornene-1,3-dicarboximido indole-3-acetate (IAA-NHND), phthalimido indole-3-acetate (IAA-NHP), naphthalimido indole-3-acetate (IAA-NHN), 4-nitrophenyl indole-3-acetate (IAA-4NP), 8-quinolyl indole-3-acetate (IAA-8HQ)] were prepared and characterized. Their kinetics of aminolysis with butylamine, piperidine, and pyrrolidine in acetonitrile were investigated. In general, the observed pseudo-first-order rate constants, k(obs), fit the two-term rate equation k(obs) = k1[amine] + k2[amine]2. For the aminolysis of six of the esters with piperidine there was no measurable k2 term. The 8-hydroxyquinoline ester and N-hydroxynaphthalimide ester of indole-3-acetic acid had no measurable k2 term for aminolysis with either pyrrolidine or piperidine. In general, the reactivity of the esters increased with increasing acidity of the conjugate acid of the nucleofuge and with increasing base strength of the nucleophilic amine. The IAA ester of NHP was observed to be ca. 100-fold more reactive than the IAA ester of 4NP although the pK(a)'s of the leaving groups are nearly the same. In all cases low activation energies were observed.