methyl Z-geissoschizoate | 101400-33-3

• 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: methyl Z-geissoschizoate
• 英文别名: methyl [(2R-(2α,3Z,12bβ))-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]acetate；methyl 2-[(2R,3Z,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]acetate
• CAS: 101400-33-3
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: FNXYSQNRXOSXLX-NBHIXCLXSA-N

物化性质

• 沸点：
  483.3±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

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：

  methyl Z-geissoschizoate 在 sodium tetrahydroborate 、 正丁基锂 、 溶剂黄146 、 二异丙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 16-epi Z isositsirikine
  参考文献：
  名称：

  Winterfeldt, Ekkehard; Freund, Ralf, Liebigs Annalen der Chemie, 1986, # 7, p. 1262 - 1267

  摘要：

  DOI：
• 作为产物：
  描述：

  <<2R-(2α,3Z,12bβ)>-3-ethylidene-1,2,3,4,6,7,12,12b-octahydro-4-oxoindolo<2,3-a>quinolizin-2-yl>-acetate 在 sodium tetrahydroborate 、 molecular sieve 、 triethyloxonium hexaflourophosphate 作用下， 生成 methyl Z-geissoschizoate
  参考文献：
  名称：

  Winterfeldt, Ekkehard; Freund, Ralf, Liebigs Annalen der Chemie, 1986, # 7, p. 1262 - 1267

  摘要：

  DOI：

文献信息

• Total syntheses of (+)-geissoschizine, (.+-.)-geissoschizine, and (.+-.)-(Z)-isositsirikine. Stereocontrolled synthesis of exocyclic double bonds by stereospecific iminium ion-vinylsilane cyclizations
  作者：Larry E. Overman、Albert J. Robichaud

  DOI：10.1021/ja00183a046

  日期：1989.1

  Syntheses via la cyclisation du [methoxycarbonyl-2' trimethylsilyl-3' pentene-3' yl]-1 methylene-2 tetrahydro-1,2,3,4 β-carbolinium-2

  通过环化合成 [甲氧基羰基-2'三甲基甲硅烷基-3'戊烯-3'基]-1亚甲基-2四氢-1,2,3,4β-咔啉-2
• Syntheses of (±)-Z-Geissoschizol, (±)-3-epi-Z-Geissoschizol, (±)-Corynantheidol, (±)-Dihydrocorynantheol, (±)-3-epi-Dihydrocorynantheol and the Corresponding Corynan-17-oic Acid Methyl Esters
  作者：Mauri Lounasmaa、Reija Jokela、Birgit Tirkkonen、Jari Miettinen、Minna Halonen

  DOI：10.3987/com-91-5922

  日期：——

  The utility of the Claisen rearrangement using carefully separated, diastereoisomeric allylic alcohols (1a) and (1b) in the preparation of (+/-)-Z-geissoschizol (4a), (+/-)-3-epi-Z-geissoschizol (4b), (+/-)-corynantheidol (7a), (+/-)-dihydrocorynantheol (8a), (+/-)-3-epi-dihydrocorynantheol (8b) and the corresponding corynan-17-oic acid methyl esters (3a, 3b, 5a, 6a and 6b) is shown. Special attention is paid to the stereochemical outcome of catalytic (PtO2) hydrogenation of the C(20) Z-ethylidene side chain.
• New, Short Synthesis of (±)-Geissoschizine
  作者：Mauri Lounasmaa、Reija Jokela、Jari Miettinen、Minna Halonen

  DOI：10.3987/com-92-6049

  日期：——

  A short, easy way to prepare indole alkaloid (+/-)-geissoschizine (1) is described.
• Cleavage of the C-20 Ethylidene Side-Chain of Deformyl-Z- and Deformyl-E-geissoschizine Derivatives Utilizing the Modified Polonovski Reaction
  作者：Mauri Lounasmaa、Reija Jokela、Minna Halonen、Jari Miettinen

  DOI：10.3987/com-93-6477

  日期：——

  Cleavage of the C-20 ethylidene side-chain of deformyl-Z-geissoschizine (1) and deformyl-E-geissoschizine (2), and their N(a)-Boc derivatives (11) and (12), utilizing the modified Polonovski reaction, is described. Mechanistic considerations are presented.
• Preparation and Conformational Study of Deformyl-Z- and Deformyl-E-geissoschizine Epimers and Na-Boc Derivatives, and Their Nb-Oxides
  作者：Mauri Lounasmaa、Reija Jokela、Pirjo Hanhinen、Christiane Laine、Ulla Anttila

  DOI：10.3987/com-96-7503

  日期：——

  Syntheses are reported for deformylgeissoschizine isomers (1-4) and their N-a-Boc derivatives (5-8), as well as for their N-b-oxides (cis and trans) (9-13) and (16-20). Predominant conformations of the compounds were determined by nmr measurements.