(8SR,13aSR)-8-(3,4-dimethoxybenzyl)-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline

• 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: (8SR,13aSR)-8-(3,4-dimethoxybenzyl)-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline
• 英文别名: (8RS,13aRS)-8-(3,4-dimethoxybenzyl)-2,3,10,11-tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline；(8R,13aR)-8-[(3,4-dimethoxyphenyl)methyl]-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
• 化学式: C₃₀H₃₅NO₆
• 分子量: 505.611
• InChiKey: LMCYQLWLTBYTGH-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (8SR,13aSR)-8-(3,4-dimethoxybenzyl)-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到8-epi-javaberine A
  参考文献：
  名称：

  Total Synthesis of 8-epi-Javaberine A and Javaberine A

  摘要：

  The total synthesis of berberine alkaloid javaberine A was examined. The B/C ring of berberine was successfully constructed by sequential Bischler-Napieralski cyclization-reduction protocols, and final demethylation afforded both javaberine A and its epimer.

  DOI：

  10.3987/com-13-s(s)101
• 作为产物：
  描述：

  N-(3,4-二甲氧基苯乙基)-2-(3,4-二甲氧基苯基)乙酰胺 在 甲醇 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 20.17h， 生成 (8SR,13aSR)-8-(3,4-dimethoxybenzyl)-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline
  参考文献：
  名称：

  Total Synthesis of 8-epi-Javaberine A and Javaberine A

  摘要：

  The total synthesis of berberine alkaloid javaberine A was examined. The B/C ring of berberine was successfully constructed by sequential Bischler-Napieralski cyclization-reduction protocols, and final demethylation afforded both javaberine A and its epimer.

  DOI：

  10.3987/com-13-s(s)101

文献信息

• Synthetic studies on javaberine A: Construction of the tetrahydroprotoberberine framework based on a double hydroamination strategy
  作者：Yasutomo Yamamoto、Hiromi Baba、Miki Toriyama、Junpei Matsuoka、Akari Miyawaki、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2023.133788

  日期：2024.1

  The tetrahydroprotoberberine framework of javaberine A was synthesized by repeated hydroamination of dienylamine as the key step. The selection of the reaction solvents and additives highly influenced the reaction pathway and stereoselectivity, and stepwise hydroamination with optimal reaction conditions effectively constructed the tetrahydroprotoberberine skeleton.

  以二烯胺重复氢胺化为关键步骤，合成了爪哇素A的四氢原小檗碱骨架。反应溶剂和添加剂的选择极大地影响了反应路径和立体选择性，在最佳反应条件下逐步加氢胺化有效地构建了四氢原小檗碱骨架。
• Stereoselective Construction of a Berberine C-8 Benzyl Group for the Synthesis of Javaberine Derivatives
  作者：Yasutomo Yamamoto、Rina Kakigi、Mai Nakano、Ayana Ueno、Akari Miyawaki、Kiyoshi Tomioka

  DOI：10.3987/com-19-s(f)36

  日期：——

  Diastereoselective synthesis of 8-benzyltetrahydroprotoberberines was examined. Although Stevens rearrangement of N-benzylxylopinine resulted in poor yield and diastereoselectivity, benzylation of tetracyclic iminium successfully gave H8-H14 trans-benzyltetrahydroprotoberberines with high stereoselectivity.