trimethyl 1,3-dihydro-3-oxo-4,5,6-isobenzofurantricarboxylate | 128408-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: trimethyl 1,3-dihydro-3-oxo-4,5,6-isobenzofurantricarboxylate
• 英文别名: trimethyl 3-oxo-1,3-dihydro-4,5,6-isobenzofurantricarboxylate；5,6,7-tris(carbomethoxy)-2(3H)benzofuranon；5,6,7-tri(carbomethoxy)phthalide；trimethyl 3-oxo-1H-2-benzofuran-4,5,6-tricarboxylate
• CAS: 128408-52-6
• 化学式: C₁₄H₁₂O₈
• 分子量: 308.244
• InChiKey: SGDIZXQTFMGJON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-丙炔-1-醇 、 丁炔二酸二甲酯 在 Karstedt’s catalyst 锌 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 以91%的产率得到trimethyl 1,3-dihydro-3-oxo-4,5,6-isobenzofurantricarboxylate
  参考文献：
  名称：

  One-pot synthesis of benzolactones and lactams via a cobalt-catalyzed regioselective [2 + 2 + 2] cocyclotrimerization of alkynyl alcohols and amines with propiolates

  摘要：

  描述了一种高效的方法，通过钴催化的[2 + 2 + 2]共聚三聚反应，将炔醇和炔胺与丙炔酸盐合成苯内酯和苯内酰胺。

  DOI：

  10.1039/b509731b

文献信息

• Prop-2-ynyl alcohol as a precursor to the η¹-ethenyl ligand
  作者：Joseph M. O'Connor、Kristin Hiibner

  DOI：10.1039/c39950001209

  日期：——

  In the presence of water the unsaturated iridium(III) metallacyclopentadiene halide complex [graphic omitted]R)(PPh3)2Cl (1, R = CO2Me) undergoes reaction with prop-2-ynyl alcohol, or methyl prop-2-ynyl ether at room temperature to give the η1-ethenyl complex [graphic omitted]R)(PPh3)2(CO)(η1-CHCH2)(3, R = CO2Me) in quantitative yield.

  在水的存在下，不饱和铱（III）金属环戊二烯卤化物络合物[省略图形]R)(PPh3)2Cl（1，R = CO2Me）在室温下与丙炔醇或丙炔基甲基醚发生反应，生成定量产物的η1-乙烯基络合物[省略图形]R)(PPh3)2(CO)(η1-CHCH2)(3，R = CO2Me)。
• Diazadienes as control ligands in homogeneous catalysis XVIII. Palladacyclopentadienes and platinacyclopentadienes and the co-cyclotrimerization of various alkynes
  作者：Heindirk tom Dieck、Christina Munz、Christiane Müller

  DOI：10.1016/0022-328x(90)87071-k

  日期：1990.2
• Iridium Complex-Catalyzed Highly Selective Cross [2 + 2 + 2] Cycloaddition of Two Different Monoynes:  2:1 Coupling versus 1:2 Coupling
  作者：Ryo Takeuchi、Yoshihiko Nakaya

  DOI：10.1021/ol035330d

  日期：2003.10.1

  Highly selective cross [2 + 2 + 2] cycloaddition of two different monoynes is achieved by using a catalytic amount of [Ir(cod)Cl](2) and ligand. The ligand had a considerable effect on the reaction. When 1,2-bis(diphenylphosphino)ethane was used, two molecules of dimethyl acetylenedicarboxylate (DMAD) reacted with one molecule of a monoyne to give the 2:1 coupling product. When 1,2-bis(dipentafluorophenylphosphino)ethane was used instead of dppe, one molecule of DMAD reacted with two molecules of a monoyne to give the 1:2 coupling product.