(+/-)-20-Epipseudovincadifformine | 73836-92-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 鸡蛋花型生物碱
• 英文名称: (+/-)-20-Epipseudovincadifformine
• 英文别名: 20-epi-Ψ-vincadifformine；(+/-)-pseudovincadifformine；20-Epipseudovincadifformine；methyl (1S,12R,14S,19R)-14-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-10-carboxylate
• CAS: 73836-92-7
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: HVESDSXDWBFBHK-AFAMQEBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-20-Epipseudovincadifformine 在 次氯酸叔丁酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Syntheses of 20'-deoxyvinblastine, 20'-deoxyleurosidine, 20'-deoxyvincovaline, 20'-epi-20'-deoxyvincovaline, and 20'-deoxyvincristine and its 20'-epimer through racemic and enantioselectively generated intermediates. New syntheses of D/E-cis- and trans-.PSI.-vincadifformines and D/E-cis- and -trans-20-epi-.PSI.-vincadifformines

  摘要：

  DOI：

  10.1021/jo00275a029
• 作为产物：
  描述：

  3-乙酰基-5-溴吡啶乙烯缩酮 在 palladium on activated charcoal 、 对甲苯磺酸 盐酸 、 potassium permanganate 、 lithium aluminium tetrahydride 、 正丁基锂 、 18-冠醚-6 、 三氟化硼乙醚 、 氢气 、 monosodium salt of ethylene glycol 、 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 苯 为溶剂， -78.0~95.0 ℃ 、303.98 kPa 条件下， 反应 39.92h， 生成 (+/-)-20-Epipseudovincadifformine
  参考文献：
  名称：

  Synthesis of 20-epipseudoaspidospermidine, 20-epidehydropseudoaspidospermidine, and 20-epipseudovincadifformine

  摘要：

  DOI：

  10.1021/jo00194a013

文献信息

• Studies in biomimetic alkaloid syntheses. 5. Studies syntheses of .psi.-vincadifformine, 20-epi-.psi.-vincadifformine, pandoline, 20-epipandoline, and the C-16 epimeric(carbomethoxy)velbanamines
  作者：Martin E. Kuehne、Curtis L. Kirkemo、Thomas H. Matsko、John C. Bohnert

  DOI：10.1021/jo01304a023

  日期：1980.8
• Total Syntheses of Vincadifformine, 3-Oxovincadifformine, Pseudo- and 20-<i>epi</i>-Pseudovincadifformine, Tabersonine, and Δ¹⁸-Tabersonine through Radical Reactions and Heck Reactions
  作者：Martin E. Kuehne、Tiansheng Wang、Pamela J. Seaton

  DOI：10.1021/jo960607r

  日期：1996.1.1

  The pentacyclic alkaloids vincadifformine (9), psi-vincadifformine (15), and epi-psi-vincadifformine (16) could be synthesized by intramolecular free-radical-induced cyclizations of the tetracyclic intermediates 7, 8, and 18, which were respectively obtained by condensation of the indoloazepine 1 with 2-(phenylselenyl)butyraldehyde and subsequent N-b-alkylation of the resulting tetracyclic amines 2 and 3, or from condensation of (phenylselenyl)acetaldehyde with the alkylated indoloazepine 17. The intermediates 2 and 3 also gave 3-oxovincadifformine (21) by an intermolecular radical alkylation with methyl acrylate. Their alkylation with (Z)-1,3-diiodopropene, phenyl selenoxide elimination, and intramolecular Heck reactions provided tabersonine (24) and 18,19-didehydrotabersonine (27).
• Synthesis of vinca alkaloids and related compounds. 64. Total syntheses of (.+-.)-pseudovincadifformine and (.+-.)-20-epipseudovincadifformine
  作者：Gyorgy Kalaus、Istvan Greiner、Maria Kajtar-Peredy、Janos Brlik、Lajos Szabo、Csaba Szantay

  DOI：10.1021/jo00074a039

  日期：1993.10

  Using our previously reported convergent synthetic strategy, secondary amine 6 and aldehyde 9 reacted to give tetracyclic esters 10 and 11, which readily led to pentacyclic lactams 14-16. Selective reduction of these products gave (+/-)-pseudovincadifformine (4), (+/-)-20-epipseudovincadifformine (5), and (+/-)-14-epipseudovincadifformine (20). Aldehyde 23 was also prepared and could be directly used for synthesizing (+/-)-20-epipseudovincadifformine (5). The introduction of the double bond into ring D of the pseudoaspidospermane skeleton was successfully achieved to obtain 21-oxopseudotabersonine (30).
• KUEHNE, MARTIN E.;BORNMANN, WILLIAM G., J. ORG. CHEM., 54,(1989) N4, C. 3407-3420
  作者：KUEHNE, MARTIN E.、BORNMANN, WILLIAM G.

  DOI：——

  日期：——