2,6-二乙酰氨基苯甲酸 | 7758-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,6-二乙酰氨基苯甲酸
• 中文别名: 细胞色素c551.5(9CI)
• 英文名称: 2,6-di(acetylamino)benzoic acid
• 英文别名: 2,6-bis(acetamido)benzoic acid；2,6-Bis-acetamino-benzoesaeure；2,6-Diacetylaminobenzoesaeure；2,6-Diacetamidobenzoic acid
• CAS: 7758-61-4
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: NABNXFSMKRRBSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  545.1±45.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-二乙酰氨基苯甲酸 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 19.5h， 生成 2-(t-BuC6H4)3CCONH-6-n-BuCONHC6H3COOH
  参考文献：
  名称：

  Synthesis and structures of soluble magnesium and zinc carboxylates containing intramolecular NH⋯O hydrogen bonds in nonpolar solvents

  摘要：

  含有分子内NH⋯O氢键的镁和锌羧酸盐在非极性溶剂中表现出快速的顺式-反式异构化，并通过添加等摩尔配体转化为阴离子三羧酸盐。

  DOI：

  10.1039/c5dt00053j

文献信息

• Contribution of Intramolecular NH···O Hydrogen Bonds to Magnesium–Carboxylate Bonds
  作者：Taka-aki Okamura、Junko Nakagawa

  DOI：10.1021/ic400671v

  日期：2013.10.7

  Mg–carboxylate bond at the trans position. In contrast, a weak Mg–carboxylate bond strengthens the Mg–O(water) bond, probably increasing the acidity. Based on the experimental results and theoretical calculations, a new switching mechanism is proposed. In the proposed mechanism, the acidity of the coordinated water on magnesium is controlled during catalytic hydrolysis in endonuclease.

  合成了一系列含有分子内NH···O氢键的羧酸镁配合物。通过X射线分析确定它们的分子结构。与配位氧原子的直接NH···O氢键延长了Mg-O键，而与羰基的氢键缩短了Mg-O键。双NH···O氢键显着降低了羧酸根阴离子的碱度，并阻止了与Mg离子呈反式配位。然而，成功地获得了顺式-二羧酸盐配合物。水与Mg 2+离子的强配位可稳定反式处弱的Mg-羧酸盐键位置。相反，弱的Mg-羧酸盐键会增强Mg-O（水）键，可能会增加酸度。基于实验结果和理论计算，提出了一种新的切换机制。在提出的机理中，在核酸内切酶催化水解过程中控制了配位水对镁的酸度。
• Regulation of the Hydrolytic Activity of Mg²⁺-Dependent Phosphatase Models by Intramolecular NH···O Hydrogen Bonds
  作者：Taka-aki Okamura、Ryosuke Furuya、Kiyotaka Onitsuka

  DOI：10.1021/ja509006x

  日期：2014.10.22

  Magnesium-dependent phosphatase models containing intramolecular NH...O hydrogen bonds were synthesized and structurally characterized by X-ray analysis. The Mg-O bond distances varied with the mode of the hydrogen bonds. H-1 NMR spectra in nonpolar solvents revealed that the acidity of the coordinated water molecule was regulated by the hydrogen bonds. Further, stoichiometric hydrolysis of phosphoric ester significantly depended on the hydrogen bonds. Zinc analogues showed similar but smaller dependencies, which suggest the indispensable role of Mg2+ ion in the activation of the enzymes.
• Polymeric and dimeric magnetic properties of square planar Cu(II) species controlled by hydrogen bond networks: [CuIIOCO-2,6-(CH3CONH)2C6H32(H2O)2]·nH2O (n = 1, 4)
  作者：Yusuke Yamada、Norikazu Ueyama、Taka-aki Okamura、Wasuke Mori、Akira Nakamura

  DOI：10.1016/s0020-1693(97)06144-6

  日期：1998.7
• Synthesis and structures of soluble magnesium and zinc carboxylates containing intramolecular NH⋯O hydrogen bonds in nonpolar solvents
  作者：Taka-aki Okamura、Ryosuke Furuya、Kiyotaka Onitsuka

  DOI：10.1039/c5dt00053j

  日期：——

  Magnesium and zinc carboxylates containing intramolecular NH⋯O hydrogen bonds showed a fast trans–cis isomerization in nonpolar solvents and were converted into anionic tris(carboxylate)s by the addition of an equimolar ligand.

  含有分子内NH⋯O氢键的镁和锌羧酸盐在非极性溶剂中表现出快速的顺式-反式异构化，并通过添加等摩尔配体转化为阴离子三羧酸盐。