(13aβ,13bβ,13cα)-13a-ethyl-2,3,5,12,13,13a,13b,13c-octahydro-12-oxo-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Eburnan型生物碱
• 英文名称: (13aβ,13bβ,13cα)-13a-ethyl-2,3,5,12,13,13a,13b,13c-octahydro-12-oxo-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine
• 英文别名: (15R,18S,19R)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8-tetraen-17-one
• 化学式: C₁₉H₂₂N₂O
• 分子量: 294.396
• InChiKey: IHXYTRONABMTQV-GBESFXJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (13aβ,13bβ,13cα)-13a-ethyl-2,3,5,12,13,13a,13b,13c-octahydro-12-oxo-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以80%的产率得到象牙酮宁
  参考文献：
  名称：

  Alkaloid Synthesis via Intramolecular Imino Diels-Alder Chemistry: Total Synthesis of (.+-.)-Eburnamonine

  摘要：

  A novel strategy, featuring an intramolecular imino Diels-Alder reaction, for the construction of the pentacyclic framework of eburnamonine is detailed.

  DOI：

  10.1021/jo00103a006
• 作为产物：
  描述：

  2-(3-ethyl-3,4,5,6-tetrahydropyridin-3-yl)-1-(3-vinylindol-1-yl)ethanone 在 camphor-10-sulfonic acid 、 lithium perchlorate 作用下， 以 乙醚 为溶剂， 以96%的产率得到(13aβ,13bβ,13cα)-13a-ethyl-2,3,5,12,13,13a,13b,13c-octahydro-12-oxo-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine
  参考文献：
  名称：

  Alkaloid Synthesis via Intramolecular Imino Diels-Alder Chemistry: Total Synthesis of (.+-.)-Eburnamonine

  摘要：

  A novel strategy, featuring an intramolecular imino Diels-Alder reaction, for the construction of the pentacyclic framework of eburnamonine is detailed.

  DOI：

  10.1021/jo00103a006

文献信息

• Alkaloid Synthesis via Intramolecular Imino Diels-Alder Chemistry: Total Synthesis of (.+-.)-Eburnamonine
  作者：Michael D. Kaufman、Paul A. Grieco

  DOI：10.1021/jo00103a006

  日期：1994.12

  A novel strategy, featuring an intramolecular imino Diels-Alder reaction, for the construction of the pentacyclic framework of eburnamonine is detailed.
• Intramolecular Imino Diels−Alder Reaction of a 3-Vinyl Indole:  Application to a Total Synthesis of (±)-Eburnamonine
  作者：Paul A. Grieco、Michael D. Kaufman

  DOI：10.1021/jo9909960

  日期：1999.10.1

  The intramolecular [4 + 2] cycloaddition of imine 1 has been examined under a variety of conditions including thermal; catalysis by acid, lithium cation, and Florisil; and the use of 5.0 M lithium perchlorate in diethyl ether. Cycloadduct 2 was transformed into (+/-)-eburnamonine 3 using acid catalysis. Substrate 1 was prepared by coupling indole-3-carboxaldehyde 7 with the activated p-nitrophenyl ester 9. Subsequent methylenation of 10 gave rise to 11, which upon exposure to fluoride ion provided imine 1.