1,2-Dimethoxy-6-methoxycarbonyl-4,5,6,6a-tetrahydro-7H-dibenzo-chinolin | 100022-14-8

• 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: 1,2-Dimethoxy-6-methoxycarbonyl-4,5,6,6a-tetrahydro-7H-dibenzo-chinolin
• 英文别名: N-Methoxycarbonyl-N-nornuciferine；methyl 1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-6-carboxylate
• CAS: 100022-14-8
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: NZPPZYPCWOGFIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-Dimethoxy-6-methoxycarbonyl-4,5,6,6a-tetrahydro-7H-dibenzo-chinolin 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以66%的产率得到nuciferine
  参考文献：
  名称：

  Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives

  摘要：

  A concise route to armepavine 1 and nuciferine 2 and 3, which can be isolated from the leaves of Nelumbo nucifera (Nymphaceae), has been achieved in which the longest linear sequence is only six steps from commercially available benzaldehyde in 28%, 21%, and 20% overall yield, respectively. The key transformations in the synthesis are the radical cyclization of aryl bromide with Bu3SnH and the Pictet-Spengler reaction of N-substituted amine with aldehyde.

  DOI：

  10.1080/00397910903435411
• 作为产物：
  描述：

  methyl 1-[(2-bromophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 palladium diacetate potassium carbonate 作用下， 以 二甲胺 为溶剂， 以58%的产率得到1,2-Dimethoxy-6-methoxycarbonyl-4,5,6,6a-tetrahydro-7H-dibenzo-chinolin
  参考文献：
  名称：

  通过直接芳基化合成阿朴啡生物碱并使其多样化

  摘要：

  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)

  DOI：

  10.1002/ejoc.200600674

文献信息

• Intramolecular ortho-arylation of phenols utilized in the synthesis of the aporphine alkaloids (±)-lirinidine and (±)-nuciferine
  作者：Gregory D. Cuny

  DOI：10.1016/j.tetlet.2003.09.026

  日期：2003.10

  A palladium-mediated intramolecular phenol ortho-arylation reaction applied to the construction of aporphine alkaloids is reported. Most significantly, the efficiency of this transformation was enhanced by the utilization of trialkylphosphine (i.e. tricyclohexylphosphine) or trialkylphosphonium salts (i.e. di-tert-butylmethyl-phosphonium tetrafluoroborate) as co-catalysts in the presence of cesium carbonate. This methodology was employed in the syntheses of the aporphine alkaloids (+/-)-lirinidine and (+/-)-nuciferine. (C) 2003 Elsevier Ltd. All rights reserved.
• 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)
• Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives
  作者：Chia-Fu Chang、Chu-Yun Huang、Yu-Chao Huang、Kuan-Yu Lin、Yean-Jang Lee、Chau-Jong Wang

  DOI：10.1080/00397910903435411

  日期：2010.11.3

  A concise route to armepavine 1 and nuciferine 2 and 3, which can be isolated from the leaves of Nelumbo nucifera (Nymphaceae), has been achieved in which the longest linear sequence is only six steps from commercially available benzaldehyde in 28%, 21%, and 20% overall yield, respectively. The key transformations in the synthesis are the radical cyclization of aryl bromide with Bu3SnH and the Pictet-Spengler reaction of N-substituted amine with aldehyde.