2,4-bis[[(cis,cis)-2,4-dioxo-1,5,7-tris((benzyloxy)methyl)-3-azabicyclo[3.3.1]non-7-carboxylic]] acid m-xylene | 182184-41-4

• 分子结构分类: 有机化合物
• 英文名称: 2,4-bis[[(cis,cis)-2,4-dioxo-1,5,7-tris((benzyloxy)methyl)-3-azabicyclo[3.3.1]non-7-carboxylic]] acid m-xylene
• CAS: 182184-41-4
• 化学式: C₇₄H₇₆N₂O₁₄
• 分子量: 1217.42
• InChiKey: SFYCBAPFJYXUDM-XYYPCNNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.81
• 重原子数：
  90.0
• 可旋转键数：
  28.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  204.74
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,4-bis[[(cis,cis)-2,4-dioxo-1,5,7-tris((benzyloxy)methyl)-3-azabicyclo[3.3.1]non-7-carboxylic]] acid m-xylene 在 diphenyl guanidine 作用下， 以 苯 为溶剂， 生成 (1S,5R,7S)-1,5,7-Tris-benzyloxymethyl-3-[2,4-dimethyl-5-((1S,5R,7S)-1,5,7-tris-benzyloxymethyl-7-carboxy-2,4-dioxo-3-aza-bicyclo[3.3.1]non-3-yl)-phenyl]-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid anion
  参考文献：
  名称：

  Energetics of a Low Barrier Hydrogen Bond in Nonpolar Solvents

  摘要：

  A measure of the strength of a low barrier hydrogen bond (LBHB) in apolar organic media was obtained using synthetic molecules derived from Kemp's triacid. The structures feature unusually rigid conformations that enforce intramolecular hydrogen bonds in a dicarboxylic acid, its corresponding acid-amide and their respective conjugate bases. Analysis of proton and deuterium NMR spectra established the formation of a LBHB in the conjugate base of the diacid and a conventional hydrogen bond in the conjugate base of the acid-amide. Through deprotonation equilibria with organic bases, it was determined that the conjugate base of the diacid was more stable than the conjugate base of the acid-amide by 2.4 kcal/mol in benzene and 1.4 kcal/mol in dichloromethane. These figures set the upper limits for the free energy of the additional stabilization arising from the LBHB at 25 degrees C. This value is far lower than many estimates but is closer to the recent determinations of Schwartz and Drueckhammer.

  DOI：

  10.1021/ja960288l
• 作为产物：
  描述：

  Kemp's anhydride acid 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2,4-bis[[(cis,cis)-2,4-dioxo-1,5,7-tris((benzyloxy)methyl)-3-azabicyclo[3.3.1]non-7-carboxylic]] acid m-xylene
  参考文献：
  名称：

  Energetics of a Low Barrier Hydrogen Bond in Nonpolar Solvents

  摘要：

  A measure of the strength of a low barrier hydrogen bond (LBHB) in apolar organic media was obtained using synthetic molecules derived from Kemp's triacid. The structures feature unusually rigid conformations that enforce intramolecular hydrogen bonds in a dicarboxylic acid, its corresponding acid-amide and their respective conjugate bases. Analysis of proton and deuterium NMR spectra established the formation of a LBHB in the conjugate base of the diacid and a conventional hydrogen bond in the conjugate base of the acid-amide. Through deprotonation equilibria with organic bases, it was determined that the conjugate base of the diacid was more stable than the conjugate base of the acid-amide by 2.4 kcal/mol in benzene and 1.4 kcal/mol in dichloromethane. These figures set the upper limits for the free energy of the additional stabilization arising from the LBHB at 25 degrees C. This value is far lower than many estimates but is closer to the recent determinations of Schwartz and Drueckhammer.

  DOI：

  10.1021/ja960288l