4,9,10-Trimethoxy-benzo[c]chromen-6-one | 185986-00-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4,9,10-Trimethoxy-benzo[c]chromen-6-one
• 英文别名: 4,9,10-Trimethoxybenzo[c]chromen-6-one
• CAS: 185986-00-9
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: NWGCOZOPSPKLEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,9,10-Trimethoxy-benzo[c]chromen-6-one 在 盐酸 、 氢氧化钾 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 生成 (2,2',3,3'-tetramethoxy)-biphenyl-6-yl N-methyl-acetamide
  参考文献：
  名称：

  A versatile approach to the synthesis of 4,5-dioxoaporphine and 3,4-dioxocularine alkaloids. One-Pot sequential ring formation from arylacetamides

  摘要：

  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

  DOI：

  10.1016/s0040-4039(97)82963-2
• 作为产物：
  描述：

  1-吲哚-2,3-二甲氧基苯 在 palladium diacetate 、 pyridinium chlorochromate 作用下， 生成 4,9,10-Trimethoxy-benzo[c]chromen-6-one
  参考文献：
  名称：

  A versatile approach to the synthesis of 4,5-dioxoaporphine and 3,4-dioxocularine alkaloids. One-Pot sequential ring formation from arylacetamides

  摘要：

  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

  DOI：

  10.1016/s0040-4039(97)82963-2

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.