(-)-isocaryachine | 65634-33-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (-)-isocaryachine
• 英文别名: (1S,12S)-15-methoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaen-16-ol
• CAS: 65634-33-5
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: SMMBTQGVTOTRAA-GJZGRUSLSA-N

物化性质

• 沸点：
  453.8±45.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  乙酸酐 、 (-)-isocaryachine 在 碘甲烷 作用下， 以 xylene 为溶剂， 反应 48.0h， 生成 [(1S,12S)-20-acetyl-15-methoxy-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaen-16-yl] acetate
  参考文献：
  名称：

  Preparation of N-Alkylnorpavines via Competitive N-Dealkylation of Quaternary Pavines

  摘要：

  N-Alkyl quaternary pavine salts were converted into N-alkyl tertiary pavines by refluxing ethanolamine, via a competitive N-dealkylation mechanism. The following N-dealkylation order was observed: benzyl > allyl > Me > Et > Pr-n greater than or equal to (n)Bu. Further study indicated that N-alkyl- and N-acylpavines could be obtained from N-methyl tertiary pavines in a one-pot reaction (acid anhydride/allyl bromide or alkyl halide, reflux). This finding provides an alternative method for preparing N-alkyl tertiary pavines.

  DOI：

  10.3987/com-96-7400
• 作为产物：
  描述：

  在 sodium hydrogen telluride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以79%的产率得到(-)-isocaryachine
  参考文献：
  名称：

  Lee, Shoei-Sheng; Liu, Yi-Chu; CHang, Shu-Hwei, Heterocycles, 1993, vol. 36, # 9, p. 1971 - 1974

  摘要：

  DOI：

文献信息

• Pavinane and isopavinane alkaloids
  作者：S.F. Dyke、R.G. Kinsman、P. Warren、A.W.C. White

  DOI：10.1016/s0040-4020(01)93611-7

  日期：1978.1

  (−)-Caryachine (9) and (−)-Reframoline (10) have been synthesised from a common intermediate; this confirms the absolute configuration in the isopavinane series deduced previously by application of the aromatic chirality rule. This also represents the first synthesis of an optically active pavinane alkaloid.

  （-）-卡里卡因（9）和（-）-拉喹啉（10）是从一种常见的中间体合成的；这证实了先前通过应用芳香族手性法则推导的异链烷烃系列的绝对构型。这也代表了旋光pavinane生物碱的首次合成。
• Lead Tetraacetate Oxidation on Caryachine, A Phenolic Pavine
  作者：Chi-Ming Chiou、Shoei-Sheng Lee

  DOI：10.1002/jccs.199700058

  日期：1997.8

  AbstractLead tetraacetate oxidation on caryachine, a pavine alkaloid possessing a phenolic group at the position para to the N‐methine, in dichloromethane yielded four products — 10‐acetoxy‐O‐acetyl‐caryachine, 10‐acetoxycaryachine, 7‐acetoxy‐O‐acetylcaryachine and (6S, 11R, 12R)‐11‐acetoxy‐O‐acetyl‐caryachine. The reaction took place via adoption of an acetoxy group at a position majorly ortho to the phenolic group, but very minorly at the desired benzylic position para to the phenolic group.