(+)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-2-one | 112459-14-0

• 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: (+)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-2-one
• 英文别名: trans-2-Oxo-3-ethyl-1.2.3.4.6.7.12.12b-octahydro-indolo<2.3-a>chinolizin；3α-Ethyl-1,2,3,4,6,7,12,12bα-octahydro-indolo(2,3-a)chinolizin；16,17-dinor-corynan-15-one；(3S,12bS)-3-ethyl-3,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-one
• CAS: 112459-14-0
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: HIBBYIKNXPWWOI-NHYWBVRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-2-one 在 palladium on activated charcoal potassium tert-butylate 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-2-yl acetic acid ethylester
  参考文献：
  名称：

  Andreae, Siegfried; Blasko, Gabor; Szantay, Csaba, Journal fur praktische Chemie (Leipzig 1954), 1987, vol. 329, # 2, p. 374 - 376

  摘要：

  DOI：
• 作为产物：
  描述：

  2-ethyl-3,3-(ethylenedioxy)-N-<<1-(phenylsulfonyl)-2-indolyl>methylene>butylamine 在 盐酸 、 potassium tert-butylate 、 sodium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 乙醇 、 苯 为溶剂， 反应 40.5h， 生成 (+)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-2-one
  参考文献：
  名称：

  Studies on the synthesis of the indolo[2,3-a]quinolizidine system

  摘要：

  DOI：

  10.1021/jo00284a037

文献信息

• Access to Electron-Rich Arene-Fused Hexahydroquinolizinones through a Gold-Catalysis-Initiated Cascade Process
  作者：Lianzhu Liu、Liming Zhang

  DOI：10.1002/anie.201203303

  日期：2012.7.16

  Golden Cascade: With a tethered, electron‐rich arene as the internal nucleophile, a gold‐catalyzed amide cyclization to an alkyne initiates a cascade process that ends with a Ferrier rearrangement. Electron‐rich arene‐bearing hexahydroquinolizin‐2‐ones are formed in good yields and can be converted into indole alkaloids in only a few steps.

  黄金级联：以束缚的、富电子的芳烃作为内部亲核试剂，金催化的酰胺环化成炔引发级联过程，以费里尔重排结束。富含电子的芳烃六氢喹啉-2-酮以良好的产率形成，只需几步即可转化为吲哚生物碱。
• Rapid construction of tetrahydropyridine scaffolds <i>via</i> formal imino Diels–Alder reactions of Schiff bases and Nazarov reagents
  作者：Yen-Ku Wu、Viresh H. Rawal

  DOI：10.1039/c9ob01880h

  日期：——

  Described is a one-flask, two-step method for the synthesis of highly functionalized piperidines. The process involves formal [4 + 2] cycloadditions of Schiff bases and Nazarov reagents, followed by facile elaborations of the initial cycloadducts. Notably, these aza-annulations are facilitated by protic solvents and proceed smoothly under ambient conditions, without other additives. The synthetic utility

  描述了一种用于合成高度官能化的哌啶的一烧瓶，两步方法。该过程涉及席夫碱和纳扎罗夫试剂的正式[4 + 2]环加成反应，然后是初始环加合物的简便修饰。值得注意的是，质子溶剂促进了这些氮杂环化反应，并且在环境条件下无需其他添加剂即可顺利进行。通过（±）-丁苯那嗪的简洁，会聚合成，进一步展示了该环空方案的综合用途。
• Synthetic Studies in Indolo[2,3-a]quinolizidine System
  作者：Venkatachalam S. Giri、Parasuraman Jaisankar、Ranjan K. Manna、James N. Shoolery、Paul Keifer

  DOI：10.1016/0040-4020(95)00581-r

  日期：1995.1

  Synthesis of trans-3-ethyl-1,2,3,4,6,7,12,12b-octa-hydroindolo[2,3-a]quinolizin-2-one (1) and assignment of stereo chemistry of the diastereoisomeric alcohols, 3-(α-hydroxyethyl)-1, 2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-ethylene thioketals (4a-4d) has been discussed.

  反式-3-乙基-1,2,3,4,6,7,12,12b-八氢吲哚[2,3-a]喹诺嗪-2-酮（1）的合成和非对映异构体的立体化学分配已经讨论了醇，3-（α-羟乙基）-1、2,3,4,6,7,12,12b-八氢吲哚并[2,3-a]喹啉锌-2-乙烯硫缩酮（4a-4d）。
• Asymmetric synthesis of the corynantheine alkaloids via an intramolecular Blaise reaction. (-)-Corynantheidol and (-)-dihydrocorynantheol
  作者：Richard L. Beard、A. I. Meyers

  DOI：10.1021/jo00006a024

  日期：1991.3

  An asymmetric total synthesis of the corynantheine family of alkaloids has been accomplished, leading to corynantheidol (1a) and dihydrocorynantheol (1b). Formal syntheses to corynantheidine and dihydrocorynantheine are also shown. The key to this asymmetric route is the use of (1) chiral beta-carboline formamidines, which allow high degrees of diastereoselection at C-3 with chloroacetonitrile, and (2) a new version of the Blaise reaction using Zn-Ag couple and ultrasonic radiation. These two synthetic techniques combine to allow an efficient entry into the title compounds. The overall yield of 1a was 16.4% in seven steps from starting carboline 5.
• Calabash curare alkaloids. Synthetic study in the C-fluorocurine-mavacurine series
  作者：Dennis D. O'Rell、Fred G. H. Lee、V. Boekelheide

  DOI：10.1021/ja00764a052

  日期：1972.5