(1S)-1-[(12bS)-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-3-yl]ethanol | 23100-13-2

• 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: (1S)-1-[(12bS)-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-3-yl]ethanol
• CAS: 23100-13-2；61755-64-4；61755-65-5；66609-37-8；66609-38-9；66965-07-9；66965-08-0
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: ZOPSRKMJIMWMSQ-ZBEGNZNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(12bS)-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-3-yl]ethanol 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 73.0h， 生成 corynan-17-oic acid methyl ester
  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

• Claisen orthoester rearrangement in the direct preparation of Z-isositsirikine and Z-geissoschizine derivatives possessing the right oxidation state at C-17
  作者：Mauri Lounasmaa、Pirjo Hanhinen、Reija Jokela

  DOI：10.1016/0040-4020(95)00477-p

  日期：1995.7

  In the cases of trialkyl 3,3-dialkoxyorthopropionates [triethyl 3,3-diethoxyorthopropionate 14b (or 3,3-diethoxymethylketene diethylacetal 20b) and trimethyl 3,3-dimethoxyorthopropionate 14 a (or 3,3-dimethoxymethylketene dimethylacetal 20a)], the intermediate ketene acetals 25a,b do not rearrange according to the Claisen mechanism to form compounds 26a,b and/or 27a,b possessing two RO-functions at

  利用烯丙醇1（或2）和3-甲氧基ortbopropionate三甲基丙烯酸13a进行的Claisen原酸酯重排导致Z-异三烷衍生物21a-22a（或23a-24a）在C-17处具有一个RO功能。在三烷基3,3- dialkoxyorthopropionates的情况下[三乙基3,3- diethoxyorthopropionate 14B（或3,3-二乙diethoxymethylketene 20B）和三甲基3,3- dimethoxyorthopropionate 14（或3,3-二甲基缩醛dimethoxymethylketene 20A）]，则中间乙烯酮缩醛25a，b不会根据克莱森机理进行重排以形成化合物26a，b和/或27a，b在C-17上具有两个RO功能。描述了中间体原酸酯的合成，即3-甲氧基原丙酸三甲酯13a，3，3-二甲氧基原丙酸三甲酯14a，反式-3-甲氧基原丙酸三甲酯2
• Hanhinen, Pirjo; Nurminen, Tomi; Jokela, Reija, Heterocycles, 1994, vol. 38, # 9, p. 2027 - 2044
  作者：Hanhinen, Pirjo、Nurminen, Tomi、Jokela, Reija、Lounasmaa, Mauri

  DOI：——

  日期：——
• Claisen Orthoester Rearrangement in the Direct Preparation of Deplancheine Derivatives Possessing a Malonyl Group at C-15
  作者：Mauri Lounasmaa、Pirjo Hanhinen

  DOI：10.3987/com-96-7538

  日期：——

  The Claisen orthoester rearrangement utilizing allylic alcohols (1) and (2), and triethyl ortho-2-ethoxycarbonylacetate (= ethyl triethyl orthomalonate) (4) leads directly to deplancheine derivatives (12 - 14) possessing a malonyl group at C-15. Compounds (12 - 14) represent the prototype of highly desired intermediates for the preparation of Corynanthe alkaloids and similar compounds.
• The Claisen rearrangement in the preparation of geissoschizine isomers
  作者：Birgit Tirkkonen、Jari Miettinen、Jaana Salo、Reija Jokela、Mauri Lounasmaa

  DOI：10.1016/s0040-4020(01)87031-9

  日期：1994.3

  The Claisen rearrangement of vinyl allyl ether 3 in refluxing toluene leads to a mixture of (+/-)-($) under bar Z-geissoschizine 5 and (+/-)-15-epi-($) under bar E-geissoschizine 6 [= (+/-)-3-epi-($) under bar E-geissoschizine 6'], whereas vinyl allyl ether 4, under the same reaction conditions, affords only (+/-)-15-epi-($) under bar Z-geissaschizine 15 [= (+/-)3-epi-($) under bar Z-geissoschizine 15']. No (+/-)-($) under bar E-geissoschizine 16 was formed. However, the formation of (+/-)-15-epi-($) under bar E-geissoschizine 6 [= (+/-)-3-epi-($) under bar E-geissoschizine 6'], which has earlier been transformed to (+/-)-($) under bar E-geissoschizine 16, represents a new, formal total synthesis of (+/-)-($) under bar E-geissoschizine 16. A conformational study of the prepared compounds, mainly based on nmr measurements, is presented.
• 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.