(+/-)-(Z)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine | 76549-66-1

• 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: (+/-)-(Z)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
• 英文别名: (Z)-deplancheine；(3Z)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine
• CAS: 76549-66-1
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: GVGJKCCVRKFWAF-OIXVIMQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 在 盐酸 、 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 86.08h， 生成 (+/-)-(Z)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
  参考文献：
  名称：

  A total synthesis of the alkaloid deplancheine

  摘要：

  DOI：

  10.1016/s0040-4039(00)92601-7

文献信息

• Total syntheses of enantiomerically enriched R-(+)- and S-(–)-deplancheine
  作者：Nadiya Sydorenko、Craig A. Zificsak、Aleksey I. Gerasyuto、Richard P. Hsung

  DOI：10.1039/b503862f

  日期：——

  Total syntheses of indoloquinolizidine alkaloid (+/-)-, R-(+)-, and S-(-)-deplancheine are described here. The synthesis features an enantioselective intramolecular formal aza-[3 + 3] cycloaddition for the construction of the quinolizidine CD-ring. This application serves to introduce a new synthetic strategy for the synthesis of indoloquinolizidine alkaloids.

  此处描述了吲哚并喹喔啉生物碱（+/-）-，R-（+）-和S-（-）-去甲十氢蝶呤的总合成。该合成具有对映选择性分子内形式的氮杂-[3 + 3]环加成反应，用于构建喹喔啉CD环。该申请旨在为吲哚并喹喔啉生物碱的合成引入新的合成策略。
• Stereocontrolled synthesis of exocyclic trisubstituted double bonds by stereospecific iminium ion-vinylsilane cyclizations. A short synthetic route to indoloquinolizidine alkaloids
  作者：Larry E. Overman、Thomas C. Malone

  DOI：10.1021/jo00148a013

  日期：1982.12
• Imine-enamine annelation: stereoselective syntheses of (±)-deplancheine
  作者：Luisella Calabi、Bruno Danieli、Giordano Lesma、Giovanni Palmisano

  DOI：10.1016/s0040-4039(00)87282-2

  日期：1982.1
• Mandal, Sukhendu B.; Pakrashi, Satyesh C., Heterocycles, 1987, vol. 26, # 6, p. 1557 - 1562
  作者：Mandal, Sukhendu B.、Pakrashi, Satyesh C.

  DOI：——

  日期：——
• Synthesis and Conformational Study of Indolo[2,3-a]quinolizidine-3-ethan-1'-ols: Intermediates for the Synthesis of Deplancheine and Flavopereirine
  作者：Mauri Lounasmaa、Kimmo Karinen、Arto Tolvanen

  DOI：10.3987/com-97-7816

  日期：——

  The synthesis and stereostructures of all four indolo[2,3-a]quinolizidine-3-ethan-1'-ols are described. The two alcohols with an axial side chain exist principally in the conformation where the C/D ring junction is trans, which is favoured by an intramolecular hydrogen bond between the hydroxyl group and the N-b-atom. Dehydration of the four alcohols with P2O5 in each case led to a mixture consisting of E-deplancheine and Z-deplancheine. The three side products were two 3-vinyl isomers, one of which can be converted to deplancheine via double bond isomerization, and 3-ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine, which is a precursor of flavopereirine.