bis-N-benzamidomethyl ether | 113660-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis-N-benzamidomethyl ether
• 英文别名: benzamidomethyl ether；N,N'-(2-oxa-propanediyl)-bis-benzamide；N,N'-(2-Oxa-propandiyl)-bis-benzamid；Bis-benzoylaminomethyl-ether；N-{[(Benzoylamino)methoxy]methyl}benzamide；N-(benzamidomethoxymethyl)benzamide
• CAS: 113660-19-8
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: DPSXPLAMZYYMER-UHFFFAOYSA-N

物化性质

• 沸点：
  584.2±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯并-15-冠醚-5 、 bis-N-benzamidomethyl ether 在 PPA 作用下， 反应 0.33h， 生成 4',5'-di-(N-benzamidomethyl)benzo-15-crown-5
  参考文献：
  名称：

  大杂环。27.苯并冠醚的酰胺甲基化

  摘要：

  DOI：

  10.1007/bf00473449
• 作为产物：
  描述：

  聚合甲醛 、 苯甲酰胺 在 potassium carbonate 作用下， 以 水 为溶剂， 以57%的产率得到N-羟甲基苯甲酰胺
  参考文献：
  名称：

  Mechanism of hydrolysis of benzamidomethyl derivatives of phenols and its implications for prodrug design

  摘要：

  A series of O-benzamidomethyl derivatives of phenols was synthesized, and their rates of hydrolysis were investigated. The hydrolyses of the compounds follow pseudo-first-order kinetics resulting in quantitative and rapid regeneration of the phenol. The rates of hydrolysis were shown to be dependent on phenol nucleofugicity as well as the pK(a) of the amide. The mechanism of hydrolysis apparently involves an elimination of the phenol anion from the conjugate base of the amide (E1cB-like).

  DOI：

  10.1021/jo00032a020

文献信息

• LUKYANENKO, N. G.;PASTUSHOK, V. N.;TONYA, L. E.;KOSTYANOVSKIJ, R. G., XIMIYA GETEROTSIKL. SOED.,(1987) N 8, 1039-1042
  作者：LUKYANENKO, N. G.、PASTUSHOK, V. N.、TONYA, L. E.、KOSTYANOVSKIJ, R. G.

  DOI：——

  日期：——
• Macroheterocycles. 27. Amidomethylation of benzo-crown ethers
  作者：N. G. Luk'yanenko、V. N. Pastushok、L. E. Tonya、R. G. Kostyanovskii

  DOI：10.1007/bf00473449

  日期：1987.8
• Mechanism of hydrolysis of benzamidomethyl derivatives of phenols and its implications for prodrug design
  作者：John J. Getz、Richard J. Prankerd、Kenneth B. Sloan

  DOI：10.1021/jo00032a020

  日期：1992.3

  A series of O-benzamidomethyl derivatives of phenols was synthesized, and their rates of hydrolysis were investigated. The hydrolyses of the compounds follow pseudo-first-order kinetics resulting in quantitative and rapid regeneration of the phenol. The rates of hydrolysis were shown to be dependent on phenol nucleofugicity as well as the pK(a) of the amide. The mechanism of hydrolysis apparently involves an elimination of the phenol anion from the conjugate base of the amide (E1cB-like).