2-(benzoylamino)benzyl benzoate | 112222-87-4

• 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: 2-(benzoylamino)benzyl benzoate
• 英文别名: 2-(benzamido)benzyl benzoate；2-benzamidobenzyl benzoate；1-benzoylamino-2-benzoyloxymethyl-benzene；1-Benzoylamino-2-benzoyloxymethyl-benzol；(2-Benzamino-benzyl)-benzoat；(2-Benzamidophenyl)methyl benzoate；(2-benzamidophenyl)methyl benzoate
• CAS: 112222-87-4
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: KVVORWCDIJWURC-UHFFFAOYSA-N

物化性质

• 熔点：
  112-115 °C
• 沸点：
  428.1±28.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(benzoylamino)benzyl benzoate 在 氢氧化钾 作用下， 生成 2-(苯甲酰基氨基)苄醇
  参考文献：
  名称：

  Raiford; Clark, Journal of the American Chemical Society, 1926, vol. 48, p. 487

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(苯甲酰基氨基)苄醇 生成 2-(benzoylamino)benzyl benzoate
  参考文献：
  名称：

  Polymorphic Diversity: N-Phenylbenzamide as a Possible Polymorphophore

  摘要：

  In this work, we identify and describe a moiety that may be capable of encouraging the formation of polymorphs. Four new N-phenylbenzamide-based compounds have been synthesized yielding four pairs of polymorphs upon recrystallization. The structures of these have been discussed and compared with the previously reported polymorphs of N[2-(hydroxymethyl)phenyl]benzamide. The results indicate that the conformation of the N-phenylbenzamide group is generally constant but is sometimes altered by the crystal packing. The N-phenylbenzamide group is capable of intermolecular N-H center dot center dot center dot O hydrogen bonding but requires a change in conformation which is generally resisted by the molecule. As a consequence, weak forces such as C-H center dot center dot center dot O, C-H center dot center dot center dot N, C-H center dot center dot center dot pi, and pi center dot center dot center dot pi interactions play significant but varying roles in these structures. One possible reason for the varying nature of the pi center dot center dot center dot pi interactions may be due to the variation of the electrostatic potential across the N-phenylbenzamide group in which negative and positive regions alternate across the face of the molecule. It is the combination of all these attributes that possibly leads to polymorphism being observed in the structures reported here.

  DOI：

  10.1021/cg400356s

文献信息

• ‘Green’ methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid
  作者：Ashok K. Prasad、Vineet Kumar、Shashwat Malhotra、Vasulinga T. Ravikumar、Yogesh S. Sanghvi、Virinder S. Parmar

  DOI：10.1016/j.bmc.2005.04.038

  日期：2005.7

  Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a 'green' alternative and mild reaction condition protocol to conventional pyridine-benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide-ionic liquid combination has been successfully

  离子液体1-甲氧基乙基-3-甲基咪唑鎓甲磺酸盐中的苯甲酰氰已被用作常规吡啶-苯甲酰氯系统的“绿色”替代方案，反应条件温和，可用于核糖（核糖和脱氧核糖两者）的有效和选择性苯甲酰化系列）。苯甲酰基氰化物-离子液体组合的使用已成功扩展到酚，芳族胺，苄醇，脂肪族二醇，3-氨基苯酚和2-氨基苄基醇的高效苯甲酰化，这表明该苯甲酰化体系的多功能性。
• Raiford; Couture, Journal of the American Chemical Society, 1924, vol. 46, p. 2312
  作者：Raiford、Couture

  DOI：——

  日期：——
• Raiford; Clark, Journal of the American Chemical Society, 1926, vol. 48, p. 487
  作者：Raiford、Clark

  DOI：——

  日期：——
• Polymorphic Diversity: <i>N</i>-Phenylbenzamide as a Possible Polymorphophore
  作者：Caitlin F. Zipp、Heini W. Dirr、Manuel A. Fernandes、Helder M. Marques、Joseph P. Michael

  DOI：10.1021/cg400356s

  日期：2013.8.7

  In this work, we identify and describe a moiety that may be capable of encouraging the formation of polymorphs. Four new N-phenylbenzamide-based compounds have been synthesized yielding four pairs of polymorphs upon recrystallization. The structures of these have been discussed and compared with the previously reported polymorphs of N[2-(hydroxymethyl)phenyl]benzamide. The results indicate that the conformation of the N-phenylbenzamide group is generally constant but is sometimes altered by the crystal packing. The N-phenylbenzamide group is capable of intermolecular N-H center dot center dot center dot O hydrogen bonding but requires a change in conformation which is generally resisted by the molecule. As a consequence, weak forces such as C-H center dot center dot center dot O, C-H center dot center dot center dot N, C-H center dot center dot center dot pi, and pi center dot center dot center dot pi interactions play significant but varying roles in these structures. One possible reason for the varying nature of the pi center dot center dot center dot pi interactions may be due to the variation of the electrostatic potential across the N-phenylbenzamide group in which negative and positive regions alternate across the face of the molecule. It is the combination of all these attributes that possibly leads to polymorphism being observed in the structures reported here.