dimethyl 2-(3-acetylindol-2-yl)malonate | 244757-41-3

• 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: dimethyl 2-(3-acetylindol-2-yl)malonate
• 英文别名: dimethyl 2-(3-acetyl-1H-indol-2-yl)propanedioate
• CAS: 244757-41-3
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: ROFROMGXYGNZFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(3-acetylindol-2-yl)malonate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.25h， 生成 methyl 2-(3-acetylindol-2-yl)acetate
  参考文献：
  名称：

  Nucleophilic Substitution Reaction of 3-Acetyl-1-methoxyindole and Its Application for the Synthesis of Novel 2-Substituted Methyl 2,3-Dihydro-1-methyl-3-oxo-5H-pyrido[4,3-b]indole-4-carboxylates

  摘要：

  A simple synthetic route was established for 3-acetyl-1-methoxyindole, which was found to undergo nucleophilic substitution reactions selectively at the 2-position. Applying the reaction, novel 2-substituted methyl 2,3-dihydro-1-methyl-3-oxo-5H-pyrido[4,3-b]indole-4-carboxylates were prepared.

  DOI：

  10.3987/com-99-8608
• 作为产物：
  描述：

  1-甲氧基-1H-吲哚 在 偶氮二异丁腈 、 potassium tert-butylate 、 三正丁基氢锡 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 25.33h， 生成 dimethyl 2-(3-acetylindol-2-yl)malonate
  参考文献：
  名称：

  Nucleophilic Substitution Reaction of 3-Acetyl-1-methoxyindole and Its Application for the Synthesis of Novel 2-Substituted Methyl 2,3-Dihydro-1-methyl-3-oxo-5H-pyrido[4,3-b]indole-4-carboxylates

  摘要：

  A simple synthetic route was established for 3-acetyl-1-methoxyindole, which was found to undergo nucleophilic substitution reactions selectively at the 2-position. Applying the reaction, novel 2-substituted methyl 2,3-dihydro-1-methyl-3-oxo-5H-pyrido[4,3-b]indole-4-carboxylates were prepared.

  DOI：

  10.3987/com-99-8608

文献信息

• Syntheses of Wasabi Phytoalexin (Methyl 1-Methoxyindole-3-carboxylate) and Its 5-Iodo Derivative, and Their Nucleophilic Substitution Reactions
  作者：Masanori Somei、Asuka Tanimoto、Hitomi Orita、Fumio Yamada、Toshiharu Ohta

  DOI：10.3987/com-00-s(i)12

  日期：——

  A simple synthetic method for methyl 1-methoxyindole-3-carboxylate, a phytoalexin isolated from Wasabia japonica, syn. Eutrema wasabi, and its 5-iodo derivative is reported. They underwent nucleophilic substitution reactions selectively at the 2-position.