methyl 15-epi-Z-geissoschizoate | 223687-36-3

• 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 15-epi-Z-geissoschizoate
• 英文别名: methyl 2-[(2S,3Z,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]acetate
• CAS: 223687-36-3
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: FNXYSQNRXOSXLX-MIRXMIAISA-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：

  methyl 15-epi-Z-geissoschizoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以62%的产率得到[(2S,5R,12bS)-3-Eth-(Z)-ylidene-5-oxy-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Preparation and Conformational Study of Deformyl-Z- and Deformyl-E-geissoschizine Epimers and Na-Boc Derivatives, and Their Nb-Oxides

  摘要：

  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.

  DOI：

  10.3987/com-96-7503
• 作为产物：
  描述：

  (1S)-1-[(12bS)-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-3-yl]ethanol 在 氢氧化钾 、 乙酰氯 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 113.0h， 生成 methyl 15-epi-Z-geissoschizoate
  参考文献：
  名称：

  Syntheses of (±)-Z-Geissoschizol, (±)-3-epi-Z-Geissoschizol, (±)-Corynantheidol, (±)-Dihydrocorynantheol, (±)-3-epi-Dihydrocorynantheol and the Corresponding Corynan-17-oic Acid Methyl Esters

  摘要：

  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.

  DOI：

  10.3987/com-91-5922

文献信息

• 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.
• 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.