trans-13-hydroxy-2,3-dimethoxy-8-oxotetrahydroprotoberberine | 87168-73-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: trans-13-hydroxy-2,3-dimethoxy-8-oxotetrahydroprotoberberine
• 英文别名: 13-hydroxy-2,3-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquino[3,2-a]isoquinolin-8-one；(13S,13aR)-13-hydroxy-2,3-dimethoxy-5,6,13,13a-tetrahydroisoquinolino[2,1-b]isoquinolin-8-one
• CAS: 87168-73-8
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: GJMABTNQEWWUBP-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-13-hydroxy-2,3-dimethoxy-8-oxotetrahydroprotoberberine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以74%的产率得到trans-13-hydroxy-2,3-dimethoxytetrahydroprotoberberine
  参考文献：
  名称：

  Marsden, Richard; MacLean, David B., Canadian Journal of Chemistry, 1984, vol. 62, p. 1392 - 1399

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]-2-iodobenzamide 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 偶氮二异丁腈 、 三正丁基氢锡 、 二甲基二环氧乙烷 、 potassium carbonate 作用下， 以 甲醇 、 三乙胺 、 丙酮 、 苯 为溶剂， 反应 39.25h， 生成 trans-13-hydroxy-2,3-dimethoxy-8-oxotetrahydroprotoberberine
  参考文献：
  名称：

  Dioxirane Epoxidation of 10-Membered-Ring Stilbene Lactams as Synthetic Precursors to Protoberberines

  摘要：

  Silylated stilbene lactams 1, prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene, were converted into protoberberines by dimethyldioxirane (DMD) epoxidation and subsequent acid-catalyzed cyclization of the epoxysilane with HCl. Treatment of the nonsilylated trans- and cis-stilbene derivatives with DMD afforded 13-hydroxytetrahydroprotoberberines and 13a-hydroxy-13-ketotetrahydroprotoberberines as the main products. Tetrahydroprotoberberines were also obtained in excellent yields by the reaction of both silylated and nonsilylated lactams with hydriodic acid.

  DOI：

  10.1021/jo981829n

文献信息

• A new synthesis of the protoberberine system
  作者：Richard Marsden、David B. MacLean

  DOI：10.1016/s0040-4039(00)81844-4

  日期：1983.1
• Marsden, Richard; MacLean, David B., Canadian Journal of Chemistry, 1984, vol. 62, p. 1392 - 1399
  作者：Marsden, Richard、MacLean, David B.

  DOI：——

  日期：——
• Dioxirane Epoxidation of 10-Membered-Ring Stilbene Lactams as Synthetic Precursors to Protoberberines
  作者：Gema Rodríguez、Luis Castedo、Domingo Domínguez、Carlos Saá、Waldemar Adam、Chantu R. Saha-Möller

  DOI：10.1021/jo981829n

  日期：1999.2.1

  Silylated stilbene lactams 1, prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene, were converted into protoberberines by dimethyldioxirane (DMD) epoxidation and subsequent acid-catalyzed cyclization of the epoxysilane with HCl. Treatment of the nonsilylated trans- and cis-stilbene derivatives with DMD afforded 13-hydroxytetrahydroprotoberberines and 13a-hydroxy-13-ketotetrahydroprotoberberines as the main products. Tetrahydroprotoberberines were also obtained in excellent yields by the reaction of both silylated and nonsilylated lactams with hydriodic acid.