isopropyl 6-benzyloxy-4,9-bis(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylate

• 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: isopropyl 6-benzyloxy-4,9-bis(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: Propan-2-yl 4,9-bis(methoxymethyl)-6-phenylmethoxypyrido[3,4-b]indole-3-carboxylate
• 化学式: C₂₆H₂₈N₂O₅
• 分子量: 448.519
• InChiKey: JQKJQRUHRXABSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isopropyl 6-benzyloxy-4,9-bis(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylate 在 盐酸 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以94%的产率得到阿贝卡尔
  参考文献：
  名称：

  Synthesis of β- and γ-Carbolines by the Palladium-Catalyzed Iminoannulation of Alkynes

  摘要：

  A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).

  DOI：

  10.1021/jo026317u
• 作为产物：
  描述：

  isopropyl 4-methoxy-2-butynoate 、 5-benzyloxy-3-iodo-1-(methoxymethyl)indole-2-methylene-tertbutylamine 在 palladium diacetate 、 三正丁胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以57%的产率得到isopropyl 6-benzyloxy-4,9-bis(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis of β- and γ-Carbolines by the Palladium-Catalyzed Iminoannulation of Alkynes

  摘要：

  A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).

  DOI：

  10.1021/jo026317u

文献信息

• Synthesis of β- and γ-Carbolines by the Palladium-Catalyzed Iminoannulation of Alkynes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo026317u

  日期：2002.12.1

  A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).