1-(1,4,6,7,12,12b-hexahydro-indolo[2,3-a]chinolizin-3-yl)-ethanol | 61755-65-5

• 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: 1-(1,4,6,7,12,12b-hexahydro-indolo[2,3-a]chinolizin-3-yl)-ethanol
• 英文别名: (1R)-1-[(12bS)-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-3-yl]ethanol
• CAS: 61755-65-5
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: ZOPSRKMJIMWMSQ-BZNIZROVSA-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：

  1-(1,4,6,7,12,12b-hexahydro-indolo[2,3-a]chinolizin-3-yl)-ethanol 在 盐酸 、 sodium tetrahydroborate 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 3-ethyl-1,4,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine
  参考文献：
  名称：

  Short Synthetic Route to 5,6-Dihydroflavopereirine and Flavopereirine

  摘要：

  A short synthetic route to 5,6-dihydroflavopereirine (1) and flavopereirine (2) is described.

  DOI：

  10.3987/com-96-7446
• 作为产物：
  描述：

  3-O-[(1R)-1-[(12bS)-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-3-yl]ethyl] 1-O-methyl propanedioate 在 盐酸 、 sodium tetrahydroborate 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-(1,4,6,7,12,12b-hexahydro-indolo[2,3-a]chinolizin-3-yl)-ethanol
  参考文献：
  名称：

  Short Synthesis of 14,15-Didehydro-E-deplancheine, Presumed Biosynthetic Intermediate in the Formation from Geissoschizine, of Corynanthé Alkaloids Missing the Three-Carbon Unit at C-15é

  摘要：

  A short synthesis of 14,15-didehydro-E-deplancheine (4) and its Z-analogue (5) is described.

  DOI：

  10.3987/com-95-7314

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：——
• 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.
• 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.
• NOE Difference Spectroscopy Applied in Stereochemical Investigations of Two Diastereomeric Indoloquinolizidine Alcohols, Significant in the Preparation of Geissoschizine-Type Compounds
  作者：Reija Jokela

  DOI：10.3987/com-92-6119

  日期：——

  Complete H-1-nmr data were recorded for indoloquinolizidine alcohols (2a) and (2b), significant intermediates in the preparation of geissoschizine-type compounds, and for their benzoyl derivatives (3a) and (3b). The stereochemistry was deduced from NOE measurements.