bikhaconitine | 6078-26-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: bikhaconitine
• 英文别名: (16S)-8-acetoxy-20-ethyl-1α,6α,16-trimethoxy-4-methoxymethyl-14α-veratroyloxy-aconitan-13-ol；(16S)-8-Acetoxy-20-aethyl-1α,6α,16-trimethoxy-4-methoxymethyl-14α-veratroyloxy-aconitan-13-ol；(1α,6α,14α,16β)-20-ethyl-1,6,16-trimethoxy-4-(methoxymethyl)-aconitane-8,13,14-triol, 8-acetate 14-(3,4-dimethoxybenzoate)；[(1S,2R,3R,4R,5S,6S,8R,9R,13S,16S,17R,18R)-8-acetyloxy-11-ethyl-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] 3,4-dimethoxybenzoate
• CAS: 6078-26-8
• 化学式: C₃₆H₅₁NO₁₁
• 分子量: 673.801
• InChiKey: CYIFGHJXUWZGSW-GRXCUHEDSA-N

物化性质

• 熔点：
  163.5-164°
• 沸点：
  689.74°C (rough estimate)
• 密度：
  1.1910 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  bikhaconitine 在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 生成 veratroylbikhaconine
  参考文献：
  名称：

  Khetwal, Khadga S.; Joshi, Balawant S.; Desai, Haridutt K., Heterocycles, 1992, vol. 34, # 3, p. 441 - 444

  摘要：

  DOI：

文献信息

• THE STRUCTURE OF BIKHACONITINE
  作者：Y. Tsuda、Léo Marion

  DOI：10.1139/v63-447

  日期：1963.12.1

  Aconitum spicatum Stapf has been found to contain two major alkaloids, pseudaconitine and bikhaconitine. The latter (C₃₆H₅₁O₁₁N) contains one free hydroxyl, four aliphatic methoxyl groups, one acetic and one veratric ester group, while the former (C₃₆H₅₁O₁₂N) contains the same substituents plus a second free hydroxyl. Like pseudaconitine, which forms a pyroderivative hydrolyzable to pyropseudaconine, which can be isomerized to isopyropseudaconine, bikhaconitine gives rise to pyrobikhaconitine, pyrobikhaconine, and isopyrobikhaconine. Bikhaconitine was assumed to differ from pseudaconitine in lacking one secondary hydroxyl. The correctness of this assumption was proved by the conversion of pseudaconitine into bikhaconitine and further to triacetylbikhaconine. This correlation establishes the structure of bikhaconitine and also, since pseudaconitine had previously been correlated with aconitine, establishes its absolute configuration.

  已发现 Aconitum spicatum Stapf 含有两种主要生物碱，即假乌头碱（pseudaconitine）和双乌头碱（bikhaconitine）。后者（C36H51O11N）含有一个游离羟基、四个脂肪族甲氧基、一个乙酸酯基和一个藜芦酯基，而前者（C36H51O12N）含有相同的取代基和第二个游离羟基。与假乌头原碱一样，比哈乌头原碱也会产生焦比哈乌头原碱、焦比哈乌头原碱和异焦比哈乌头原碱。假定比哈乌头碱与假乌头碱的不同之处在于缺少一个仲羟基。通过将假乌头原碱转化为比哈乌头原碱，再进一步转化为三乙酰比哈乌头原碱，证明了这一假设的正确性。这种相关性确定了比卡乌碱的结构，同时，由于假乌头碱以前曾与乌头碱相关，因此也确定了其绝对构型。
• Dunstan; Andrews, Journal of the Chemical Society, 1905, vol. 87, p. 1620,1629, 1630
  作者：Dunstan、Andrews

  DOI：——

  日期：——