deformyl-3-isogeissoschizine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: deformyl-3-isogeissoschizine
• 英文别名: methyl 2-((12b,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acetate；methyl 2-[(2S,3E,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]acetate
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: FNXYSQNRXOSXLX-IPPALFRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  deformyl-3-isogeissoschizine 生成 (+/-)-deformylgeissoschizine
  参考文献：
  名称：

  吲哚并[2,3-α]喹啉嗪衍生物的新合成：（±）-geososchizine的正式全合成

  摘要：

  已经开发了立体有规的消除方法，用于在色胺中将E-亚乙基基团转化为（±）-鹅卵石酸甲酯。

  DOI：

  10.1016/s0040-4039(01)90396-x
• 作为产物：
  描述：

  19a-homo-17-nor-coryna-18,20-diene-16,16,18-tricarboxylic acid trimethyl ester 生成 deformyl-3-isogeissoschizine
  参考文献：
  名称：

  Preparation and H(3) isomerization of C(15)-substituted deplancheine derivatives. Synthesis of geissoschizol and geissoschizine

  摘要：

  DOI：

  10.1021/jo00266a032

文献信息

• Bioinspired Divergent Oxidative Cyclizations of Geissoschizine: Total Synthesis of (–)‐17‐nor‐Excelsinidine, (+)‐16‐ <i>epi</i> ‐Pleiocarpamine, (+)‐16‐Hydroxymethyl‐Pleiocarpamine and (+)‐Taberdivarine H
  作者：Maxime Jarret、Aurélien Tap、Victor Turpin、Natacha Denizot、Cyrille Kouklovsky、Erwan Poupon、Laurent Evanno、Guillaume Vincent

  DOI：10.1002/ejoc.202000962

  日期：2020.10.31

  To synthesize excelsinidines and mavacurans alkaloids, bio‐inspired oxidative cyclizations of (+)‐geissochizine and analogues mediated by KHMDS/I2 were studied. Applied to geissoschizine, the N4–C16 bond formation led to excelsinidines core. Quaternization of the aliphatic nitrogen was necessary to access the mavacurans core (N1–C16 bond). Alternatively, 17‐nor‐excelsinidine was synthetized via an

  为了合成excelsinidines和mavacurans生物碱，研究了由KHMDS / I 2介导的（+）-geissochizine及其类似物的生物启发性氧化环化作用。应用于Geissoschizine时，N4-C16键的形成导致了Excelsinidines的核心。脂族氮的季铵化是进入马六甲聚糖核心（N1-C16键）所必需的。或者，通过α-氯内酰胺的分子内亲核取代合成17-或excelsinidine。
• Chloroformate ester-induced reductive 1,2-bond cleavage of some 1,2,3,4-tetrahydro-β-carboline derivatives
  作者：Martin J. Calverley

  DOI：10.1039/c39810001209

  日期：——

  Treatment with a chloroformate ester at –70 °C and subsequent reaction with NaBH3CN converts 1,2,5,6,11,11b-hexahydro-3H-indolo[3,2-g]indolizine and derivatives of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]-quinolizine cleanly into the corresponding C/D ring-cleaved urethane derivatives; when the order of addition of reagents is reversed in experiments performed at 0 °C, formation of stable substrate–cyanoborane

  在–70°C下用氯甲酸酯处理，然后与NaBH 3 CN反应，可转化为1,2,5,6,11,11b-六氢-3 H-吲哚并[3,2- g ]吲哚并嗪和1,2的衍生物，3,4,6,7,12,12b-八氢吲哚并[2,3- a ]-喹啉嗪干净地转化为相应的C / D环裂解的氨基甲酸酯衍生物; 当在0°C下进行的实验中颠倒试剂的添加顺序时，稳定的底物-氰基硼烷加合物的形成会与该反应竞争。
• Short syntheses of hirsutine and geissoschizine
  作者：Ernest Wenkert、Yashwant D. Vankar、Jhillu S. Yadav

  DOI：10.1021/ja00547a041

  日期：1980.12
• Total Syntheses of Pleiocarpamine, Normavacurine, and <i>C</i>-Mavacurine
  作者：Keigo Sato、Noriyuki Kogure、Mariko Kitajima、Hiromitsu Takayama

  DOI：10.1021/acs.orglett.9b01084

  日期：2019.5.3

  The total syntheses of C-mavacurine-type indole alkaloids, (+/-)-pleiocarpamine, (+/-)-normavacurine, and (+/-)-C-mavacurine, were accomplished. The key step in the syntheses was the cyclization between the metal carbenoid at C-16 and the N-1 position in a Corynanthe-type compound that was equipped with a diazo function. For this cyclization, the N-4 modification of the substrate using an amine-borane complex was indispensable to fix the molecular conformation.
• Calverley, Martin J., Journal of Chemical Research, Miniprint, 1983, # 8, p. 1848 - 1890
  作者：Calverley, Martin J.

  DOI：——

  日期：——