1-carboethoxy-2,3,4,5-tetrakis(carbometoxy)benzene | 128408-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-carboethoxy-2,3,4,5-tetrakis(carbometoxy)benzene
• 英文别名: 1-ethyl 2,3,4,5-tetramethyl benzene-1,2,3,4,5-pentacarboxylate；1-O-ethyl 2-O,3-O,4-O,5-O-tetramethyl benzene-1,2,3,4,5-pentacarboxylate
• CAS: 128408-46-8
• 化学式: C₁₇H₁₈O₁₀
• 分子量: 382.324
• InChiKey: MGAHLVKZWJGDIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  丁炔二酸二甲酯 、 丙烯酸乙酯 在 水 、 氧气 、 N,N-二甲基甲酰胺 、 palladium dichloride 作用下， 80.0 ℃ 、800.01 kPa 条件下， 反应 24.0h， 以76%的产率得到1-carboethoxy-2,3,4,5-tetrakis(carbometoxy)benzene
  参考文献：
  名称：

  PdCl₂(HNMe₂)₂-Catalyzed Highly Selective Cross [2 + 2 + 2] Cyclization of Alkynoates and Alkenes under Molecular Oxygen

  摘要：

  In the course of our study on palladium-catalyzed aerobic oxidation synthesis, We found that the PdCl2/O-2/DMF system consistently experienced DMF hydrolysis to afford PdCl2(HNMe2)(2), which is the real active catalyst for the aerobic oxidation. Although in situ DMF hydrolysis has been widely used in generating supramolecular assembly architectures, as far as we know, it is the first successful example to utilize PdCl2(HNMe2)(2) in synthetic reactions. The highly selective cross [2 + 2+2] cyclization of alkynoates and different alkenes with electron-withdrawing groups could be smoothly catalyzed by PdCl2(HNMe2)(2)/O-2/DMF to afford the corresponding functionalized pentasubstituted benzenes in good to excellent yields (70-97%). The extension of alkyne surrogates for cross [2 + 2 + 2] cyclization from special alkenes with leaving groups to simple alkenes under molecular oxygen led to a paradigm shift in arene synthesis.

  DOI：

  10.1021/jo902636g

文献信息

• Alkyne oligomerization catalyzed by molybdenum(0) complexes
  作者：G.Attilio Ardizzoia、S Brenna、G LaMonica、A Maspero、N Masciocchi

  DOI：10.1016/s0022-328x(02)01114-2

  日期：2002.4

  Three new molybdenum(0) complexes, [Mo(CO)3(Hpz)3] (1), [Mo(CO)2(Hpz)2(DMAD)2] (2), (DMAD=dimethyl acetylenedicarboxylate) and [Mo(CO)3(1-Me-imidazole)3] (3) were synthesized and characterized. Their activity and selectivity in alkyne cyclotrimerization and co-trimerization reactions was investigated. The molecular structures of 1 and 2 have been determined by unconventional powder and standard single-crystal

  三种新的钼（0）络合物[Mo（CO）3（Hpz）3 ]（1），[Mo（CO）2（Hpz）2（DMAD）2 ]（2），（DMAD =乙酰二羧酸二甲酯）和[合成并表征了Mo（CO）3（1-Me-咪唑）3 ]（3）。研究了它们在炔烃环三聚和共三聚反应中的活性和选择性。1和2的分子结构分别通过非常规粉末和标准单晶衍射方法确定。1个由C 3对称的伪八面体络合物组成，配体处于fac位置；复杂2，理想化的Ç 2对称性，由一个CO取代，并且在一个吡唑获得1由两个DMAD配体，并显示了稀有反π结合的炔属部分的配置。
• 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