3-Oxo-2-(3,4,5-tris-dodecyloxy-benzoyl)-butyric acid ethyl ester | 210709-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Oxo-2-(3,4,5-tris-dodecyloxy-benzoyl)-butyric acid ethyl ester
• CAS: 210709-56-1
• 化学式: C₄₉H₈₆O₇
• 分子量: 787.218
• InChiKey: ZXAMZTISAVGTMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.54
• 重原子数：
  56.0
• 可旋转键数：
  41.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-Oxo-2-(3,4,5-tris-dodecyloxy-benzoyl)-butyric acid ethyl ester 在 吡啶 、 sodium methylate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 生成 N-butylaminocarbonyl-6-[3,4,5-tri(dodecyloxy)phenyl]isocytosine
  参考文献：
  名称：

  Strong Dimerization of Ureidopyrimidones via Quadruple Hydrogen Bonding

  摘要：

  6-Methyl-2-butylureidopyrimidone dimerizes via four hydrogen bonds in the solid state as well as in CHCl3 solution via a donor-donor-acceptor-acceptor (DDAA) array of hydrogen bonding sites in the 4[1H]-pyrimidinone tautomer. An intramolecular hydrogen bond from the pyrimidine NH group to the urea oxygen atom preorganizes the molecules for dimerization. The dimerization constant of the dimer in CHCl3 exceeds 10(6) M-1. In CHCl3 containing DMSO, the dimer is in equilibrium with the monomeric 6[1H]-pyrimidinone tautomer. In 6-phenyl-2-butylureidopyrimidone, the 4[1H]-pyrimidinone tautomer coexists with the pyrimidin-4-ol form, which dimerizes with similar high dimerization constants via four hydrogen bonds in a DADA array. The latter tautomer predominates in derivatives with electronegative 6-substituents, like 6-nitrophenyl- and 6-trifluoromethyl-2-butylureidopyrimidone. Due to its simple preparation and high dimerization constant, the ureidopyrimidone functionality is a useful building block far supramolecular chemistry.

  DOI：

  10.1021/ja974112a
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 3,4,5-tris(dodecanyloxy)benzoyl chloride 在 sodium ethanolate 作用下， 生成 3-Oxo-2-(3,4,5-tris-dodecyloxy-benzoyl)-butyric acid ethyl ester
  参考文献：
  名称：

  Strong Dimerization of Ureidopyrimidones via Quadruple Hydrogen Bonding

  摘要：

  6-Methyl-2-butylureidopyrimidone dimerizes via four hydrogen bonds in the solid state as well as in CHCl3 solution via a donor-donor-acceptor-acceptor (DDAA) array of hydrogen bonding sites in the 4[1H]-pyrimidinone tautomer. An intramolecular hydrogen bond from the pyrimidine NH group to the urea oxygen atom preorganizes the molecules for dimerization. The dimerization constant of the dimer in CHCl3 exceeds 10(6) M-1. In CHCl3 containing DMSO, the dimer is in equilibrium with the monomeric 6[1H]-pyrimidinone tautomer. In 6-phenyl-2-butylureidopyrimidone, the 4[1H]-pyrimidinone tautomer coexists with the pyrimidin-4-ol form, which dimerizes with similar high dimerization constants via four hydrogen bonds in a DADA array. The latter tautomer predominates in derivatives with electronegative 6-substituents, like 6-nitrophenyl- and 6-trifluoromethyl-2-butylureidopyrimidone. Due to its simple preparation and high dimerization constant, the ureidopyrimidone functionality is a useful building block far supramolecular chemistry.

  DOI：

  10.1021/ja974112a