(+/-)-16-epideethyleburnamine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吲哚萘啶生物碱
• 英文名称: (+/-)-16-epideethyleburnamine
• 英文别名: desethyleburnamine；(15R,17R,19R)-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-ol
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: KOIGYXJOGRVNIS-HFBAOOFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  28.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1α,12bβ)-1-Cyanomethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (+/-)-16-epideethyleburnamine 、 (+/-)-deethyleburnamine
  参考文献：
  名称：

  Total Synthesis of (±)-Deethyleburnamonine and Vindeburnol (RU 24722) with the Corresponding Nitriles as Starting Material

  摘要：

  Cyclisation occurred during base treatment of cis-nitrile (5). The resulting new imine (6) was converted into the therapeutically important deethyleburnamonine (4). Total synthesis of vindeburnol (RU 24722) (3), another important drug, was achieved in one step starting from the trans-nitrile (9).

  DOI：

  10.3987/com-99-8486

文献信息

• Acid-catalysed epimerization of indolo[2,3-a]quinolizidine derivatives: Role of the nitrogen lone pairs in the mechanism
  作者：Mauri Lounasmaa、Mathias Berner、Martin Brunner、Harri Suomalainen、Arto Tolvanen

  DOI：10.1016/s0040-4020(98)00614-0

  日期：1998.8

  The role of the nitrogen lone pairs in the mechanism of the acid-catalysed epimerization of indolo[2,3-a]quinolizidines is investigated using lactams as model compounds. Deethyleburnamonine (3) did not epimerize with trifluoroacetic acid (TFA), whereas deethyldihydroeburnamenine (7) underwent epimerization smoothly. Under treatment with TFA, lactams 12 and 13 both epimerized with ease to a mixture

  使用内酰胺作为模型化合物，研究了氮孤对在吲哚并[2,3- a ]喹啉联苯胺的酸催化差向异构化机理中的作用。脱乙基氨磺胺碱（3）没有与三氟乙酸（TFA ）发生差向异构化，而脱乙基二氢氨苯甲氨酸（7）顺利进行了差向异构化。在用TFA处理下，内酰胺12和13均容易地差向异构为内酰胺12和13的混合物。当重复使用内酰胺18和19进行实验时，达到了类似的平衡。中级20被内酰胺12的酸催化差向异构化过程捕获（锌还原），可以得出有关该机理的结论。
• Total Synthesis of (±)-Eburnaminol and (±)-Larutensine
  作者：Mauri Lounasmaa、Esko Karvinen

  DOI：10.3987/com-92-6220

  日期：——

  Short syntheses are described for the (+/-)-forms of the recently isolated eburnane type alkaloids (-)-ebumaminol [(-)-1] and (+)-larutensine [(+)-2], and for the not yet naturally found 18-hydroxyebumamonine (3) and 16-epieburnaminol (4).
• Total Synthesis of (±)-Deethyleburnamonine and Vindeburnol (RU 24722) with the Corresponding Nitriles as Starting Material
  作者：Mauri Lounasmaa、David Din Belle、Arto Tolvanen

  DOI：10.3987/com-99-8486

  日期：——

  Cyclisation occurred during base treatment of cis-nitrile (5). The resulting new imine (6) was converted into the therapeutically important deethyleburnamonine (4). Total synthesis of vindeburnol (RU 24722) (3), another important drug, was achieved in one step starting from the trans-nitrile (9).