6-acetyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinoline | 14528-29-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 6-acetyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinoline
• 英文别名: 6-acetyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline；1-(5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-yl)ethanone
• CAS: 14528-29-1
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: AZKNTZGHGOBKGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-acetyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinoline 在 水 、 lithium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.25h， 生成 阿朴啡
  参考文献：
  名称：

  A convenient formation of aporphine core via benzyne chemistry: conformational analysis and synthesis of (R)-aporphine

  摘要：

  Total synthesis of (R)-aporphine has been accomplished by an approach that employs in the key step a sequence of transformations involving a [4+2] cycloaddition reaction followed by a hydrogen migration, leading to aporphine core in good yield, which was subjected to a 1D gradient NOE experiment, conformational analysis, and simple transformations, including a small scale resolution process, to afford enantiomericallyenriched aporphine alkaloid. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.083
• 作为产物：
  描述：

  N-(2-苯乙基)乙酰胺 在 吡啶 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 30.5h， 生成 6-acetyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinoline
  参考文献：
  名称：

  A convenient formation of aporphine core via benzyne chemistry: conformational analysis and synthesis of (R)-aporphine

  摘要：

  Total synthesis of (R)-aporphine has been accomplished by an approach that employs in the key step a sequence of transformations involving a [4+2] cycloaddition reaction followed by a hydrogen migration, leading to aporphine core in good yield, which was subjected to a 1D gradient NOE experiment, conformational analysis, and simple transformations, including a small scale resolution process, to afford enantiomericallyenriched aporphine alkaloid. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.083

文献信息

• Aporphine Alkaloid Synthesis and Diversification via Direct Arylation
  作者：Marc Lafrance、Nicole Blaquiere、Keith Fagnou

  DOI：10.1002/ejoc.200600674

  日期：2007.2

  aporphines by reaction with benzodioxole, pyridine N-oxide and pyrazine N-oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of (R)-nornuciferine and (R)-nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric

  钯催化的芳基氯化物、溴化物和碘化物的直接芳基化已被应用于通过与苯并二恶唑、吡啶 N-氧化物和吡嗪 N-氧化物反应制备新的阿朴啡类似物，包括 C2 取代的阿朴啡。直接芳基化在这些多样化反应中的成功应用突出了其不仅在收敛合成中而且在发散合成中的效用。我们还描述了 (R)-nornuciferine 和 (R)-nuciferine 的对映选择性合成，采用催化不对称转移氢化以高产率和优异的对映体过量。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• [EN] NITRIC OXIDE AND ITS BIOMEDICAL SIGNIFICANCE<br/>[FR] OXYDE NITRIQUE ET SA VALEUR BIOMÉDICALE
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2012078155A1

  公开（公告）日：2012-06-14

  A pharmaceutical composition for stimulating nitric oxide production in mammalian cells, the pharmaceutical composition including at least one compound selected from a group consisting of: 2,3-dihydroxypropyl oleate; bis(m-phenoxyphenyl) ether; 6-acetyl-5,6,6a,7-tetrahydro-4H-dibezo(de,g)quinoline; and (+)-N-(p-(2-methylbutoxy)benzylidene)-4-(2-methylbutyl)aniline.
• A convenient formation of aporphine core via benzyne chemistry: conformational analysis and synthesis of (R)-aporphine
  作者：Givago P. Perecim、Alessandro Rodrigues、Cristiano Raminelli

  DOI：10.1016/j.tetlet.2015.10.083

  日期：2015.12

  Total synthesis of (R)-aporphine has been accomplished by an approach that employs in the key step a sequence of transformations involving a [4+2] cycloaddition reaction followed by a hydrogen migration, leading to aporphine core in good yield, which was subjected to a 1D gradient NOE experiment, conformational analysis, and simple transformations, including a small scale resolution process, to afford enantiomericallyenriched aporphine alkaloid. (C) 2015 Elsevier Ltd. All rights reserved.

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