N-(2-Hydrazinocarbonyl-phenyl)-2,2-diphenyl-acetamide | 178422-77-0

• 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: N-(2-Hydrazinocarbonyl-phenyl)-2,2-diphenyl-acetamide
• 英文别名: N-[2-(hydrazinecarbonyl)phenyl]-2,2-diphenylacetamide
• CAS: 178422-77-0
• 化学式: C₂₁H₁₉N₃O₂
• 分子量: 345.401
• InChiKey: BYKSUZMTBOKRBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  84.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-Hydrazinocarbonyl-phenyl)-2,2-diphenyl-acetamide 在 吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 3-<(S)-2-Acetoxypropanoyl>amino-2-diphenylmethyl-3,4-dihydroquinazolin-4-one
  参考文献：
  名称：

  The N–N bond as a chiral axis: 3-diacylaminoquinazolinones as chiral acylating agents

  摘要：

  3-Diacylaminoquinazolinones 10 and 15 have high enough barriers to rotation around their N-N bonds to allow separation of each into diastereoisomers. Interconversion of diastereoisomers 10a and 10b occurs on heating in boiling toluene and thermodynamic parameters for this process have been measured, The barriers to rotation around the N-N bonds in analogous monoacylaminoquinazolinones are not sufficient to permit isolation of stereoisomers at room temperature unless the exocyclic nitrogen is additionally substituted e.g. by an alkyl group as in 28, X-Ray crystal structure determinations carried out on 10a, 10b, 15a and 28b confirm the presence of chiral axes, Reaction of both diastereoisomers 15a and 15b with 1-phenylethylamine takes place with exclusive reaction at the 1-acetoxypropionyl carbonyl group and with partial kinetic resolution: the preferred sense of enantioselectivity obtained is dominated by the N-N axis.

  DOI：

  10.1039/p19960001047
• 作为产物：
  描述：

  Methyl 2-[(diphenylacetyl)amino]benzoate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以91%的产率得到N-(2-Hydrazinocarbonyl-phenyl)-2,2-diphenyl-acetamide
  参考文献：
  名称：

  The N–N bond as a chiral axis: 3-diacylaminoquinazolinones as chiral acylating agents

  摘要：

  3-Diacylaminoquinazolinones 10 and 15 have high enough barriers to rotation around their N-N bonds to allow separation of each into diastereoisomers. Interconversion of diastereoisomers 10a and 10b occurs on heating in boiling toluene and thermodynamic parameters for this process have been measured, The barriers to rotation around the N-N bonds in analogous monoacylaminoquinazolinones are not sufficient to permit isolation of stereoisomers at room temperature unless the exocyclic nitrogen is additionally substituted e.g. by an alkyl group as in 28, X-Ray crystal structure determinations carried out on 10a, 10b, 15a and 28b confirm the presence of chiral axes, Reaction of both diastereoisomers 15a and 15b with 1-phenylethylamine takes place with exclusive reaction at the 1-acetoxypropionyl carbonyl group and with partial kinetic resolution: the preferred sense of enantioselectivity obtained is dominated by the N-N axis.

  DOI：

  10.1039/p19960001047

文献信息

• The N–N bond as a chiral axis: 3-diacylaminoquinazolinones as chiral acylating agents
  作者：Robert S. Atkinson、Emma Barker、Paul J. Edwards、Gordon A. Thomson

  DOI：10.1039/p19960001047

  日期：——

  3-Diacylaminoquinazolinones 10 and 15 have high enough barriers to rotation around their N-N bonds to allow separation of each into diastereoisomers. Interconversion of diastereoisomers 10a and 10b occurs on heating in boiling toluene and thermodynamic parameters for this process have been measured, The barriers to rotation around the N-N bonds in analogous monoacylaminoquinazolinones are not sufficient to permit isolation of stereoisomers at room temperature unless the exocyclic nitrogen is additionally substituted e.g. by an alkyl group as in 28, X-Ray crystal structure determinations carried out on 10a, 10b, 15a and 28b confirm the presence of chiral axes, Reaction of both diastereoisomers 15a and 15b with 1-phenylethylamine takes place with exclusive reaction at the 1-acetoxypropionyl carbonyl group and with partial kinetic resolution: the preferred sense of enantioselectivity obtained is dominated by the N-N axis.