Bicyclo[2.2.2]octa-2,5-diene-2,3,5,6-tetracarboxylic acid tetrakis-(2,4,5-trichloro-phenyl) ester | 202410-67-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Bicyclo[2.2.2]octa-2,5-diene-2,3,5,6-tetracarboxylic acid tetrakis-(2,4,5-trichloro-phenyl) ester
• CAS: 202410-67-1
• 化学式: C₃₆H₁₄Cl₁₂O₈
• 分子量: 999.938
• InChiKey: ZMZTWAYYUMYUQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.88
• 重原子数：
  56.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  、 Bicyclo[2.2.2]octa-2,5-diene-2,3,5,6-tetracarboxylic acid tetrakis-(2,4,5-trichloro-phenyl) ester 在 三乙胺 作用下， 反应 10.0h， 生成 、
  参考文献：
  名称：

  Solvent Controls Synthesis and Properties of Supramolecular Structures

  摘要：

  A template effect by solvent was found in the synthesis of self-assembled capsules. Use of aromatic solvents such as benzene, toluene, and p-xylene leads predominantly to the formation of the C-shaped molecules 3 and 6, which form hydrogen-bonded dimeric capsules. This is the medium in which the solvent-occupied dimeric capsule enjoys the greatest stability, and the best solvated surfaces with properly filled niches are formed preferentially. The dimerization constant (K-D) value and a Delta G(0) value of >14.0 kcal mol(-1) for the capsules 16 (3.3) were estimated for the first time in guest-exchange experiments. When solvents not suitable for dimerization (CHCl3 and CH2Cl2) or those solvents that compete for hydrogen bonds (DMSO and THF) were employed, only statistical yields of the stereoisomers (C-, S-, and W-shaped) were observed. Experimental evidence is presented that the solvent molecules control the covalent bond formation through molecular recognition within the monomeric tetrahedral intermediate. It is proposed that solvation effects can be treated as a subset of molecular recognition events.

  DOI：

  10.1002/(sici)1521-3765(19980807)4:8<1449::aid-chem1449>3.0.co;2-y
• 作为产物：
  描述：

  2,4,5-三氯苯酚 、 Bicyclo[2.2.2]octa-2,5-diene-2,3,5,6-tetracarboxylic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 various solvent(s) 为溶剂， 反应 30.0h， 以67%的产率得到Bicyclo[2.2.2]octa-2,5-diene-2,3,5,6-tetracarboxylic acid tetrakis-(2,4,5-trichloro-phenyl) ester
  参考文献：
  名称：

  Solvent Controls Synthesis and Properties of Supramolecular Structures

  摘要：

  A template effect by solvent was found in the synthesis of self-assembled capsules. Use of aromatic solvents such as benzene, toluene, and p-xylene leads predominantly to the formation of the C-shaped molecules 3 and 6, which form hydrogen-bonded dimeric capsules. This is the medium in which the solvent-occupied dimeric capsule enjoys the greatest stability, and the best solvated surfaces with properly filled niches are formed preferentially. The dimerization constant (K-D) value and a Delta G(0) value of >14.0 kcal mol(-1) for the capsules 16 (3.3) were estimated for the first time in guest-exchange experiments. When solvents not suitable for dimerization (CHCl3 and CH2Cl2) or those solvents that compete for hydrogen bonds (DMSO and THF) were employed, only statistical yields of the stereoisomers (C-, S-, and W-shaped) were observed. Experimental evidence is presented that the solvent molecules control the covalent bond formation through molecular recognition within the monomeric tetrahedral intermediate. It is proposed that solvation effects can be treated as a subset of molecular recognition events.

  DOI：

  10.1002/(sici)1521-3765(19980807)4:8<1449::aid-chem1449>3.0.co;2-y