3-oxovincadifformine | 55528-27-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 冬青素型生物碱
• 英文名称: 3-oxovincadifformine
• 英文别名: methyl (1R,12S,19S)-12-ethyl-15-oxo-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-10-carboxylate
• CAS: 55528-27-3
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: OQLYVMALDCKIQD-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-oxovincadifformine 在 tetraphosphorus decasulfide 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 8-thioxo-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Application of Ferrocenylalkyl Chiral Auxiliaries to Syntheses of Indolenine Alkaloids:  Enantioselective Syntheses of Vincadifformine, ψ- and 20-epi-ψ-Vincadifformines, Tabersonine, Ibophyllidine, and Mossambine

  摘要：

  Condensations of the chiral N-ferrocenylethylindoloazepines 4a,b, with the aldehydes 5, 13, 19, 29, and 32, led to tetracyclic vinylogous urethanes 6a,b and 7,14a and 14b,21a,c and 21b,d,30a and 31a, and 30b and 31b. Respectively, 6:1, 5:1, 3:1, 1.7:1, and 2:1 diastereomeric selections provided intermediates which, on cleavage of the chiral auxiliary N-substituent and subsequent elaboration of ring D of the Aspidosperma and Strychnos alkaloids, provided enantiomerically pure (-)-psi- and (-)-epi-psi-vincadifformines (1, 2), (+)-ibophyllidine (12), (+)-and (-)-vincadifformine (16a, 16b), (-)-tabersonine (27), and (-)-mossambine (41).

  DOI：

  10.1021/jo971838g
• 作为产物：
  描述：

  3-oxo-tabersonine 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以1 mg的产率得到3-oxovincadifformine
  参考文献：
  名称：

  大花干草生物碱

  摘要：

  摘要 从大花百合种子和叶子中提取的 16 种 ibogan 和 plumeran 型生物碱。3-Oxovincadifformine, 14β-hyd

  DOI：

  10.1016/0031-9422(88)80456-4

文献信息

• Nouvelle transposition du squelette aspidospermane: reactivite de la chloro-16 dehydro-1 vincadifformine dans l' acide acetique
  作者：G. Lewin、J. Poisson、J. Lamotte-Brasseur

  DOI：10.1016/0040-4020(82)80109-9

  日期：1982.1

  Heating of 16-chloro 1-dehydro vincadifformine 4a in pure acetic acid yields mainly the new compound 5 by a fragmentation-rearrangement sequence. Structure of 5 was studied by spectroscopic methods and it has been determined by X-ray crystallography of its reduction N-methylation derivative 8. The proposed mechanism for the formation of 5 is confirmed by a mass spectrometry study.

  通过裂解重排序列，在纯乙酸中加热16-氯1-脱氢长春花青碱4a主要产生新化合物5。通过光谱方法研究了5的结构，并通过X射线晶体学测定了其还原N-甲基化衍生物8的结构。质谱研究证实了所提出的形成5的机理。
• Hugel, Georgette; Laronze, Jean-Yves; Laronze, Jacqueline, Heterocycles, 1981, vol. 16, # 4, p. 581 - 590
  作者：Hugel, Georgette、Laronze, Jean-Yves、Laronze, Jacqueline、Levy, Jean

  DOI：——

  日期：——
• Calabi, Luisella; Danieli, Bruno; Lesma, Giordano, Journal of the Chemical Society. Perkin transactions I, 1982, p. 1371 - 1380
  作者：Calabi, Luisella、Danieli, Bruno、Lesma, Giordano、Palmisano, Giovanni

  DOI：——

  日期：——
• Application of Ferrocenylalkyl Chiral Auxiliaries to Syntheses of Indolenine Alkaloids:  Enantioselective Syntheses of Vincadifformine, ψ- and 20-<i>epi</i>-ψ-Vincadifformines, Tabersonine, Ibophyllidine, and Mossambine
  作者：Martin E. Kuehne、Upul K. Bandarage、Abdelhakim Hammach、Yun-Long Li、Tiansheng Wang

  DOI：10.1021/jo971838g

  日期：1998.4.1

  Condensations of the chiral N-ferrocenylethylindoloazepines 4a,b, with the aldehydes 5, 13, 19, 29, and 32, led to tetracyclic vinylogous urethanes 6a,b and 7,14a and 14b,21a,c and 21b,d,30a and 31a, and 30b and 31b. Respectively, 6:1, 5:1, 3:1, 1.7:1, and 2:1 diastereomeric selections provided intermediates which, on cleavage of the chiral auxiliary N-substituent and subsequent elaboration of ring D of the Aspidosperma and Strychnos alkaloids, provided enantiomerically pure (-)-psi- and (-)-epi-psi-vincadifformines (1, 2), (+)-ibophyllidine (12), (+)-and (-)-vincadifformine (16a, 16b), (-)-tabersonine (27), and (-)-mossambine (41).
• Alkaloids of Stemmadenia grandiflora
  作者：Ruben Torrenegra、Julio A.P. Pedrozo、Hans Achenbach、Peter Bauereiß

  DOI：10.1016/0031-9422(88)80456-4

  日期：1988.1

  Abstract Extracts from the seeds and leaves of Stemmadenia grandiflora yielded 16 alkaloids of the ibogan and plumeran type. 3-Oxovincadifformine, 14β-hyd

  摘要 从大花百合种子和叶子中提取的 16 种 ibogan 和 plumeran 型生物碱。3-Oxovincadifformine, 14β-hyd