2-(1-Benzyl-7-phenylmethoxyindol-3-yl)ethanamine | 1371592-97-0

• 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: 2-(1-Benzyl-7-phenylmethoxyindol-3-yl)ethanamine
• CAS: 1371592-97-0
• 化学式: C₂₄H₂₄N₂O
• 分子量: 356.467
• InChiKey: NIXSFAXDZZVGBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-Benzyl-7-phenylmethoxyindol-3-yl)ethanamine 在 4-二甲氨基吡啶 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 对甲苯磺酰氯 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 Methyl 5-[2-(1-benzyl-7-phenylmethoxyindol-3-yl)ethyl-(4-methylidenehexanoyl)amino]-1,3,4-oxadiazole-2-carboxylate
  参考文献：
  名称：

  Divergent Total Syntheses of (−)-Aspidospermine and (+)-Spegazzinine

  摘要：

  Divergent total syntheses of (+)-spegazzinine (1) and (-)-aspidospermine (2) and their extensions to the synthesis of C19-epi-aspidospermine and C3-epi-spegazzinine are detailed, confirming the relative stereochemistry and establishing the absolute configuration ol (+)-spegazzinine. A powerful intramolecular [4 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole provided the pentacyclic skeleton and all the requisite stereochemistry of the natural products in a single reaction that forms three rings, four C-C bonds, and five stereocenters.

  DOI：

  10.1021/ol300599p
• 作为产物：
  描述：

  7-(苄氧基)吲哚啉 在 lithium aluminium tetrahydride 、 ammonium acetate 、 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.08h， 生成 2-(1-Benzyl-7-phenylmethoxyindol-3-yl)ethanamine
  参考文献：
  名称：

  Divergent Total Syntheses of (−)-Aspidospermine and (+)-Spegazzinine

  摘要：

  Divergent total syntheses of (+)-spegazzinine (1) and (-)-aspidospermine (2) and their extensions to the synthesis of C19-epi-aspidospermine and C3-epi-spegazzinine are detailed, confirming the relative stereochemistry and establishing the absolute configuration ol (+)-spegazzinine. A powerful intramolecular [4 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole provided the pentacyclic skeleton and all the requisite stereochemistry of the natural products in a single reaction that forms three rings, four C-C bonds, and five stereocenters.

  DOI：

  10.1021/ol300599p

文献信息

• Divergent Total Syntheses of (−)-Aspidospermine and (+)-Spegazzinine
  作者：James P. Lajiness、Wanlong Jiang、Dale L. Boger

  DOI：10.1021/ol300599p

  日期：2012.4.20

  Divergent total syntheses of (+)-spegazzinine (1) and (-)-aspidospermine (2) and their extensions to the synthesis of C19-epi-aspidospermine and C3-epi-spegazzinine are detailed, confirming the relative stereochemistry and establishing the absolute configuration ol (+)-spegazzinine. A powerful intramolecular [4 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole provided the pentacyclic skeleton and all the requisite stereochemistry of the natural products in a single reaction that forms three rings, four C-C bonds, and five stereocenters.