methyl o-amidoglutaranilate | 697236-30-9

• 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 o-amidoglutaranilate
• 英文别名: Methyl 5-(2-carbamoylanilino)-5-oxopentanoate
• CAS: 697236-30-9
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: ILAYXSLJVYLQLP-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C(Solv: benzene (71-43-2))
• 沸点：
  512.9±35.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  98.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl o-amidoglutaranilate 在 sodium tetrahydroborate 、 H-mordenite 、 sodium acetate 、 sodium hydride 、 溶剂黄146 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.5h， 生成 吴茱萸次碱
  参考文献：
  名称：

  Facile zeolite induced Fischer-indole synthesis: a new approach to bioactive natural product rutaecarpine

  摘要：

  Starting from glutaric anhydride (5) we have demonstrated an elegant six-step practical synthesis of bioactive natural product rutaecarpine (1a) via o-amidoglutaranilic acid formation, esterification, chemoselective ester reduction, intramolecular dehydrative cyclizations, hydrazone formation and zeolite induced Fischer-indole synthesis with 53% overall yield. The conditions employed in the present synthesis are mild, efficient and general. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.037
• 作为产物：
  描述：

  2-氨基苯甲酰胺 在 硫酸 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 11.0h， 生成 methyl o-amidoglutaranilate
  参考文献：
  名称：

  Facile zeolite induced Fischer-indole synthesis: a new approach to bioactive natural product rutaecarpine

  摘要：

  Starting from glutaric anhydride (5) we have demonstrated an elegant six-step practical synthesis of bioactive natural product rutaecarpine (1a) via o-amidoglutaranilic acid formation, esterification, chemoselective ester reduction, intramolecular dehydrative cyclizations, hydrazone formation and zeolite induced Fischer-indole synthesis with 53% overall yield. The conditions employed in the present synthesis are mild, efficient and general. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.037

文献信息

• Facile zeolite induced Fischer-indole synthesis: a new approach to bioactive natural product rutaecarpine
  作者：Santosh B Mhaske、Narshinha P Argade

  DOI：10.1016/j.tet.2004.02.037

  日期：2004.4

  Starting from glutaric anhydride (5) we have demonstrated an elegant six-step practical synthesis of bioactive natural product rutaecarpine (1a) via o-amidoglutaranilic acid formation, esterification, chemoselective ester reduction, intramolecular dehydrative cyclizations, hydrazone formation and zeolite induced Fischer-indole synthesis with 53% overall yield. The conditions employed in the present synthesis are mild, efficient and general. (C) 2004 Elsevier Ltd. All rights reserved.