demethylaspidospermine | 2122-21-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 冬青素型生物碱
• 英文名称: demethylaspidospermine
• 英文别名: O-Demethyl-aspidospermin；O-demethylaspidospermine；1-acetyl-aspidospermidin-17-ol；1-[(1R,9R,12R,19R)-12-ethyl-6-hydroxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5-trien-8-yl]ethanone
• CAS: 2122-21-6
• 化学式: C₂₁H₂₈N₂O₂
• 分子量: 340.466
• InChiKey: XLNXVRNSNBJROM-CWJKEVGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  demethylaspidospermine 在 chiralcel AD 作用下， 以 甲醇 、 乙醚 、 正己烷 、 异丙醇 、 甲苯 为溶剂， 反应 64.0h， 生成 坚木碱 、 aspidospermine
  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：

  Methyl 5-[2-(1-benzyl-7-phenylmethoxyindol-3-yl)ethyl-(4-methylidenehexanoyl)amino]-1,3,4-oxadiazole-2-carboxylate 在 吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 氨 、 氢气 、 乙酰氯 、 三苯基膦 、 三氟乙酸酐 、 对硝基苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 邻二氯苯 、 甲苯 为溶剂， 反应 70.17h， 生成 demethylaspidospermine
  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.