tetramethyl 8,11-dioxo[4.3.3]propellane-7,9,10,12-tetracarboxylate | 67140-87-8

• 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: tetramethyl 8,11-dioxo[4.3.3]propellane-7,9,10,12-tetracarboxylate
• CAS: 67140-87-8
• 化学式: C₂₀H₂₄O₁₀
• 分子量: 424.405
• InChiKey: KROPIPJGEINLEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.14
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  139.34
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  tetramethyl 8,11-dioxo[4.3.3]propellane-7,9,10,12-tetracarboxylate 在 盐酸 、 氢氧化钾 、 肼 作用下， 反应 2.0h， 生成 Hexahydro-3a,7a-propano-indene
  参考文献：
  名称：

  Weber,R.W.; Cook,J.M., Canadian Journal of Chemistry, 1978, vol. 56, p. 189 - 192

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 1,2-环己二酮 以 甲醇 、 aq. phosphate buffer 为溶剂， 反应 72.0h， 生成 tetramethyl 8,11-dioxo[4.3.3]propellane-7,9,10,12-tetracarboxylate
  参考文献：
  名称：

  Design, synthesis and receptor affinity of novel conformationally restricted σ ligands based on the [4.3.3]propellane scaffold

  摘要：

  A series of novel diastereoisomeric sigma ligands 3 was designed, synthesized and pharmacologically evaluated. The highly rigid [4.3.3]propellane scaffold was used to fix the three dimensional orientation of the pharmacophoric moieties required for a affinity. The syn,syn-configured aminocarbamate syn,syn-3a reveals the most promising ai affinity (K-i = 77 nM) and selectivity over the 02 subtype (21-fold). The sigma(2) affinity of all four diastereomers 3 was in the low micromolar range. Analysis of the distance between the hydrophobic regions (phenyl moieties) of the diastereomers 3 led to the longest range of distances (10.3 -15.2 angstrom) for the most potent sigma(1) ligand syn,syn-3a, which is in good agreement with pharmacophore models. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.021