4,5-dioxodehydrocorydine

• 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: 4,5-dioxodehydrocorydine
• 英文别名: 1-hydroxy-2,10,11-trimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-4,5(6H)-dione；16-hydroxy-3,4,15-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,3,5,7,9(17),13,15-heptaene-11,12-dione
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: IPVCTRCEGQBADX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二甲氧基苯硼酸 在 四(三苯基膦)钯 氰化钠 、 四氯化锡 、 potassium carbonate 、 甲胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 44.0h， 生成 4,5-dioxodehydrocorydine
  参考文献：
  名称：

  钯（0）铃木交叉偶联反应是合成阿片类药物的关键步骤

  摘要：

  我们报告了一种灵活的方法，可以基于钯（0）催化的苯硼酸与空间受阻的2-溴苯基乙酸酯或溴代苯基乙酰胺的铃木交叉偶联，对4,5-二氧杂卟啉进行全合成，然后依次进行二环化的联芳基乙酰胺由草酰氯/路易斯酸。4，5-二氧杂卟啉的还原提供了对磷腈，脱氢紫杉醇和4-羟基-脱氢紫杉醇的化学选择性进入。（±）为一个三步骤的总合成- ø，ö还报道从容易获得的前体'-dimethylapomorphine。

  DOI：

  10.1016/j.tet.2004.05.014

文献信息

• A versatile approach to the synthesis of 4,5-dioxoaporphine and 3,4-dioxocularine alkaloids. One-Pot sequential ring formation from arylacetamides
  作者：Rafael Suau、Juan Manuel López-Romero、Rodrigo Rico

  DOI：10.1016/s0040-4039(97)82963-2

  日期：1996.12

  Cyclization of biarylacetamides to their phenanthrene derivatives is promoted by oxalyl chloride/stannyl chloride. The reaction proceeds with a second cyclization in which the oxalyl fragment acts as an alpha-dicarbonyl transfer agent to give 4,5-dioxoaporphine alkaloids in a single step. This double cyclization was also applied to aryloxyphenyl acetamides to give the corresponding 3,4-dioxocularine alkaloids. Decarbonylated aristocularine alkaloids were also formed in this case. Copyright (C) 1996 Elsevier Science Ltd
• Sequential bicyclization of biphenyl acetamides promoted by (COCl)2/SnCl4. Total synthesis of 4,5-dioxoaporphines
  作者：Rafael Suau、Juan Manuel López-Romero、Rodrigo Rico

  DOI：10.1016/s0040-4020(97)00923-x

  日期：1997.10

  The reaction of biphenyl acetamides with excess of oxalyl chloride/stannyl chloride offers a one pot, high-yield entry to 4,5-dioxoaporphine alkaloids. This strategy has been applied to the synthesis of 4,5-dioxodehydrocorydine starting from 1-iodo-2,3-dimethoxybenzene. The cytotoxicity of tetraoxygenated 4,5-dioxoaporphines has been evaluated. (C) 1997 Elsevier Science Ltd.
• The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids
  作者：R Suau、R Rico、F Nájera、F.J Ortiz-López、J.M López-Romero、M Moreno-Mañas、A Roglans

  DOI：10.1016/j.tet.2004.05.014

  日期：2004.6

  of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy-dehydroaporphines. A three-steps total synthesis for (±)-O,O′-dimethylapomorphine from readily

  我们报告了一种灵活的方法，可以基于钯（0）催化的苯硼酸与空间受阻的2-溴苯基乙酸酯或溴代苯基乙酰胺的铃木交叉偶联，对4,5-二氧杂卟啉进行全合成，然后依次进行二环化的联芳基乙酰胺由草酰氯/路易斯酸。4，5-二氧杂卟啉的还原提供了对磷腈，脱氢紫杉醇和4-羟基-脱氢紫杉醇的化学选择性进入。（±）为一个三步骤的总合成- ø，ö还报道从容易获得的前体'-dimethylapomorphine。

表征谱图