(-)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-2-one | 131897-80-8

• 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: cis-2-Oxo-3-ethyl-1.2.3.4.6.7.12.12b-octahydro-indolo<2.3-a>chinolizin；16,17-dinor-corynan-15-one；(3R,12bS)-3-ethyl-3,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-one
• CAS: 131897-80-8
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: HIBBYIKNXPWWOI-ABAIWWIYSA-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

• 作为产物：
  描述：

  (S)-(-)-2-[N-(1-tert-butoxy-3-methylbut-2-yl)iminomethyl]-9-methoxymethyl-1,2,3,4-tetrahydro-β-carboline 在 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 磷酸 、 银 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 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：

  Asymmetric synthesis of the corynantheine alkaloids via an intramolecular Blaise reaction. (-)-Corynantheidol and (-)-dihydrocorynantheol

  摘要：

  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.

  DOI：

  10.1021/jo00006a024

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。
• Formal Syntheses of Dihydrocorynantheine and Isorhynchophylline via Proline Catalyzed Mannich-Michael Reaction
  作者：Takashi Itoh、Hitomi Ishikawa、Ayako Tanaka、Michiko Miyazaki、Takuya Kanemitsu、Kazuhiro Nagata

  DOI：10.3987/com-09-11828

  日期：——

  Proline catalyzed Mannich-Michael reaction of 3-ethyl-3-buten-2-one with 9-tosyl-3,4-dihydro-beta-carboline proceeded in a highly stereoselective manner. The reaction was applied to formal syntheses of dihydrocorynantheine and isorhynchophylline.
• BEARD, RICHARD L.;MEYERS, A. I., J. ORG. CHEM., 56,(1991) N, C. 2091-2096
  作者：BEARD, RICHARD L.、MEYERS, A. I.

  DOI：——

  日期：——