1-hydroxy-2-methoxy-4,5,6a,7-tetrahydro-dibenzo[de,g]quinoline-6-carboxylic acid methyl ester | 634151-30-7

• 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-hydroxy-2-methoxy-4,5,6a,7-tetrahydro-dibenzo[de,g]quinoline-6-carboxylic acid methyl ester
• 英文别名: 1-Hydroxy-2-methoxy-6-methoxycarbonyl-4,5,6,6a-tetrahydro-7H-dibenzo-chinolin；methyl 1-hydroxy-2-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-6-carboxylate
• CAS: 634151-30-7
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: UXAPVJJCDKKTMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-hydroxy-2-methoxy-4,5,6a,7-tetrahydro-dibenzo[de,g]quinoline-6-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以86%的产率得到2-甲氧基-6-甲基-5,6,6a,7-四氢-4H-二苯并[de,g]喹啉-1-醇
  参考文献：
  名称：

  Intramolecular ortho-arylation of phenols utilized in the synthesis of the aporphine alkaloids (±)-lirinidine and (±)-nuciferine

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2003.09.026
• 作为产物：
  描述：

  1-(2-bromobenzyl)-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid methyl ester 在 potassium tert-butylate 作用下， 以 氨 为溶剂， 反应 3.0h， 以75%的产率得到1-hydroxy-2-methoxy-4,5,6a,7-tetrahydro-dibenzo[de,g]quinoline-6-carboxylic acid methyl ester
  参考文献：
  名称：

  液氨中的S RN 1反应通过苯酚与芳基卤化物的分子内邻位芳基化反应合成Aporphine和Homoaporphine生物碱

  摘要：

  溴代芳烃的光刺激分子内邻位芳基化反应与在液态氨中含N-取代的四氢异喹啉侧苯氧基的侧基连接，通过S RN 1反应提供了阿菲啡（54-82％产率）生物碱衍生物。该策略首次扩展到了合成高apaporphine衍生物（40％的收率）。在氮上含有吸电子基团的四氢异喹啉前体（即酰胺，磺酰胺和氨基甲酸酯）产生环化产物，而具有碱性氮的前体（即NH或NMe）要么不能产生环化产物，要么仅以低产率得到磷灰石。

  DOI：

  10.1021/jo061478+

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.
• Syntheses of Aporphine and Homoaporphine Alkaloids by Intramolecular <i>ortho</i>-Arylation of Phenols with Aryl Halides via S_RN1 Reactions in Liquid Ammonia
  作者：Silvia M. Barolo、Xin Teng、Gregory D. Cuny、Roberto A. Rossi

  DOI：10.1021/jo061478+

  日期：2006.10.1

  The photostimulated intramolecular ortho-arylation reactions of bromoarenes linked with pendant phenoxy containing N-substituted tetrahydroisoquinolines in liquid ammonia afforded aporphine (54−82% yield) alkaloid derivatives via SRN1 reactions. This strategy was extended for the first time to the synthesis of a homoaporphine derivative (40% yield). Tetrahydroisoquinoline precursors that contained

  溴代芳烃的光刺激分子内邻位芳基化反应与在液态氨中含N-取代的四氢异喹啉侧苯氧基的侧基连接，通过S RN 1反应提供了阿菲啡（54-82％产率）生物碱衍生物。该策略首次扩展到了合成高apaporphine衍生物（40％的收率）。在氮上含有吸电子基团的四氢异喹啉前体（即酰胺，磺酰胺和氨基甲酸酯）产生环化产物，而具有碱性氮的前体（即NH或NMe）要么不能产生环化产物，要么仅以低产率得到磷灰石。