(+/-)-3-oxominovincine

• 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-oxominovincine
• 英文别名: methyl (1S,12S,19S)-12-acetyl-15-oxo-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-10-carboxylate
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: MFHXHUWPPADWLA-NJDAHSKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-3-oxominovincine 在 tetraphosphorus decasulfide 、 镍 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 (+/-)-minovincine
  参考文献：
  名称：

  Synthesis of Vinca Alkaloids and Related Compounds. 90.¹ New Results in the Synthesis of Alkaloids with the Aspidospermane Skeleton. First Total Synthesis of (±)-3-Oxominovincine

  摘要：

  The tryptamine derivative 1 readily reacted with methyl 4-acetyl-5-bromopent-4-enoate (9) that had been built up from 2,4-pentanedione. On intramolecular dehydration and subsequent [4 + 2] cycloaddition, the reaction product 10 gave the epimers 12 and 13 having the D-secoaspidospermane skeleton. Compound 12 directly and 13 after epimerization yielded (+/-)-3-oxominovincine (14). Regioselective reduction of 14 furnished (+)-minovincine (17).

  DOI：

  10.1021/jo9713464
• 作为产物：
  描述：

  4-乙酰基-5-羰基己酸甲酯 在 palladium on activated charcoal 四丁基氯化铵 、 氢气 、 溴 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 、 xylene 为溶剂， 反应 75.0h， 生成 (+/-)-3-oxominovincine
  参考文献：
  名称：

  Synthesis of Vinca Alkaloids and Related Compounds. 90.¹ New Results in the Synthesis of Alkaloids with the Aspidospermane Skeleton. First Total Synthesis of (±)-3-Oxominovincine

  摘要：

  The tryptamine derivative 1 readily reacted with methyl 4-acetyl-5-bromopent-4-enoate (9) that had been built up from 2,4-pentanedione. On intramolecular dehydration and subsequent [4 + 2] cycloaddition, the reaction product 10 gave the epimers 12 and 13 having the D-secoaspidospermane skeleton. Compound 12 directly and 13 after epimerization yielded (+/-)-3-oxominovincine (14). Regioselective reduction of 14 furnished (+)-minovincine (17).

  DOI：

  10.1021/jo9713464

文献信息

• Synthesis of vinca alkaloids and related compounds. Part 101: A new convergent synthetic pathway to build up the aspidospermane skeleton. Simple synthesis of 3-oxovincadifformine and 3-oxominovincine. Attempts to produce 15β-hydroxyvincadifformine
  作者：János Éles、György Kalaus、István Greiner、Mária Kajtár-Peredy、Pál Szabó、Lajos Szabó、Csaba Szántay

  DOI：10.1016/s0040-4020(02)01179-1

  日期：2002.10

  A molecule with an indole skeleton, containing a latent acrylic ester function—acting as a diene—was produced from Nb-trityl-2-(hydroxy-methyl)-tryptamine and reacted with esters containing an aldehyde or aldehyde-equivalent structural unit, yielding 3-oxo-16,17-dihydro-Δ20-secodin-17-ol type intermediates from which dehydration, followed by [4+2]cycloaddition, furnished 3-oxovincadifformine and 3-oxominovincine

  由N b-三苯甲基-2-（羟基-甲基）-色胺产生具有吲哚骨架的分子，该分子具有潜在的丙烯酸酯功能（起二烯作用），并与含有醛或醛当量结构单元的酯反应，得到3-氧代-16,17-二氢- Δ 20 -secodin -17-醇型中间体从脱水，接着[4 + 2]环加成，陈设3- oxovincadifformine和3- oxominovincine。我们还希望将该方法用于生产15β-羟基长春新碱，但是，观察到具有吲哚骨架的二聚产物的出现，而不是预期的环加成。