2H-benzofuro<2,3,f>chromene carboxylic acid | 152821-22-2

• 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: 2H-benzofuro<2,3,f>chromene carboxylic acid
• 英文别名: 3-oxo-3H-benzofuro[3,2-f]chromene-2-carboxylic acid；3-Oxo-[1]benzofuro[3,2-f]chromene-2-carboxylic acid
• CAS: 152821-22-2
• 化学式: C₁₆H₈O₅
• 分子量: 280.237
• InChiKey: CETRFGDVOGFQBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2H-benzofuro<2,3,f>chromene carboxylic acid 在 铜 作用下， 反应 0.17h， 以85%的产率得到2H-benzofuro<2,3,f>chromenone
  参考文献：
  名称：

  An Efficient Preparation of Coumarins

  摘要：

  o-methoxyaryl-aldehydes (or -ketones) react in solid-phase with Meldrum's acid under mild conditions, to give benzylidene derivatives which are cyclized in high yield, with cold sulfuric acid to substituted 3-carboxycoumarins. Thermal decarboxylation, speed up by copper powder, provided an easy access to numerous coumarins.

  DOI：

  10.1080/00397919308013801
• 作为产物：
  描述：

  ethyl 3-oxo-3H-benzofuro[3,2-f]-1-benzopyran-2-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以67%的产率得到2H-benzofuro<2,3,f>chromene carboxylic acid
  参考文献：
  名称：

  Synthesis of novel benzofurocoumarin analogues and their anti-proliferative effect on human cancer cell lines

  摘要：

  The synthesis of five new tetracyclic benzofurocoumarin (benzopsoralen) analogues is described. Their inhibitory effects on the growth of three human tumor cell lines (MDA MB 231 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma) were evaluated, and discussed in terms of structure-activity relationship. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.005

文献信息

• Synthesis of novel benzofurocoumarin analogues and their anti-proliferative effect on human cancer cell lines
  作者：Carla S. Francisco、Lígia R. Rodrigues、Nuno M.F.S.A. Cerqueira、Ana M.F. Oliveira-Campos、Lígia M. Rodrigues

  DOI：10.1016/j.ejmech.2011.11.005

  日期：2012.1

  The synthesis of five new tetracyclic benzofurocoumarin (benzopsoralen) analogues is described. Their inhibitory effects on the growth of three human tumor cell lines (MDA MB 231 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma) were evaluated, and discussed in terms of structure-activity relationship. (C) 2011 Elsevier Masson SAS. All rights reserved.
• An Efficient Preparation of Coumarins
  作者：Francis Rouessac、Anne Leclerc

  DOI：10.1080/00397919308013801

  日期：1993.11

  o-methoxyaryl-aldehydes (or -ketones) react in solid-phase with Meldrum's acid under mild conditions, to give benzylidene derivatives which are cyclized in high yield, with cold sulfuric acid to substituted 3-carboxycoumarins. Thermal decarboxylation, speed up by copper powder, provided an easy access to numerous coumarins.