(13aS)-2,10,11-三甲氧基-6,8,13,13a-四氢-5H-异喹啉并[2,1-b]异喹啉-1-醇 | 34413-12-2

• 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
• 中文名称: (13aS)-2,10,11-三甲氧基-6,8,13,13a-四氢-5H-异喹啉并[2,1-b]异喹啉-1-醇
• 英文名称: (-)-caseadine
• 英文别名: Caseadine；(13aS)-2,10,11-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-1-ol
• CAS: 34413-12-2
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: HXHKKYNHNQVAAX-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (13aS)-2,10,11-三甲氧基-6,8,13,13a-四氢-5H-异喹啉并[2,1-b]异喹啉-1-醇 在 碘 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以52%的产率得到(-)-7,8-dehydrocaseadine iodide
  参考文献：
  名称：

  A novel oxidation stage in the chemistry of protoberberine alkaloids. Synthesis of 7,8-dehydroberbines

  摘要：

  1,2-substituted berbines, such as (-)-caseamine, (-)-caseadine and (-)-O-methylcaseadine, are partially oxidized by iodine to the 7,8-dehydroberbines, while the 2,3-substituted berbines are oxidized all the way to the protoberberinium salts. This different behaviour is interpreted in terms of the preferred cis or trans B/C quinolizidine conformation of the starting berbines.

  DOI：

  10.1016/s0040-4020(01)86534-0
• 作为产物：
  描述：

  (-)-caseamine 、 甲醇 生成 (13aS)-2,10,11-三甲氧基-6,8,13,13a-四氢-5H-异喹啉并[2,1-b]异喹啉-1-醇
  参考文献：
  名称：

  SUAU, RAFAEL;VALPUESTA, MARIA;SILVA, M. VICTORIA;PEDROSA, ANTONIO, PHYTOCHEMISTRY, 27,(1988) N 6, C. 1920-1922

  摘要：

  DOI：

文献信息

• (−)-Caseamine from Ceratocapnos heterocarpa: Structure and total synthesis
  作者：Rafael Suau、Maria Valpuesta、M.Victoria Silva、Antonio Pedrosa

  DOI：10.1016/0031-9422(88)80486-2

  日期：1988.1

  Abstract (−)-Caseamine was the major alkaloid isolated from Ceratocapnos heterocarpa. Its structure was elucidated by spectroscopic methods and by total s

  摘要 (-)-Caseamine 是从 Ceratocapnosheterocarpa 中分离出来的主要生物碱。其结构是通过光谱方法和总s
• Quaternary protoberberine alkaloids from Ceratocapnos heterocarpa
  作者：Rafael Suau、M. Victoria Silva、María Valpuesta

  DOI：10.1016/0031-9422(93)80045-t

  日期：1993.9

  Three new quaternary protoberberine alkaloids, cis-caseamine N-oxide, cis-caseadine N-oxide and caseadinium chloride were isolated from Ceratocapnos heterocarpa. Their structures and stereochemistry were determined by spectral methods and chemical correlations.

  从 Ceratocapnosheterocarpa 中分离出三种新的四元原小檗碱生物碱、cis-caseamine N-oxide、cis-caseadine N-oxide 和 caseadinium chloride。它们的结构和立体化学通过光谱方法和化学相关性确定。
• SUAU, RAFAEL;VALPUESTA, MARIA;SILVA, M. VICTORIA;PEDROSA, ANTONIO, PHYTOCHEMISTRY, 27,(1988) N 6, C. 1920-1922
  作者：SUAU, RAFAEL、VALPUESTA, MARIA、SILVA, M. VICTORIA、PEDROSA, ANTONIO

  DOI：——

  日期：——
• A novel oxidation stage in the chemistry of protoberberine alkaloids. Synthesis of 7,8-dehydroberbines
  作者：Rafael Suau、M.Victoria Silva、Maria Valpuesta

  DOI：10.1016/s0040-4020(01)86534-0

  日期：1991.7

  1,2-substituted berbines, such as (-)-caseamine, (-)-caseadine and (-)-O-methylcaseadine, are partially oxidized by iodine to the 7,8-dehydroberbines, while the 2,3-substituted berbines are oxidized all the way to the protoberberinium salts. This different behaviour is interpreted in terms of the preferred cis or trans B/C quinolizidine conformation of the starting berbines.