(E)-N-propenylidene(ethyloxy)amine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-N-propenylidene(ethyloxy)amine
• 英文别名: (E)-N-ethoxyprop-2-en-1-imine
• 化学式: C₅H₉NO
• 分子量: 99.1326
• InChiKey: URSPAOPYZOAFJO-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  O-乙基羟胺 、 丙烯醛 在 potassium dihydrogenphosphate 作用下， 反应 0.75h， 生成 (Z)-N-propenylidene(ethyloxy)amine 、 (E)-N-propenylidene(ethyloxy)amine
  参考文献：
  名称：

  The [(Methyloxy)imino]methyl Moiety as a Bioisoster of Aryl. A Novel Class of Completely Aliphatic .beta.-Adrenergic Receptor Antagonists

  摘要：

  Previous studies in the field of beta-adrenergic drugs had supported the hypothesis of the existence of a bioisosterism between the [(methyleneamino)oxy]methyl moiety (C=NOCH2, MAOMM) of type B beta-blocking drugs and the aryl (Ar) of type A beta-blocking agents. In the MAOMM, however, the carbon of the CH2 linked to the oximic oxygen possesses a hybridization (sp(3)) and a geometry different from those of the corresponding carbon of Ar which possesses an sp(2) hybridization. Furthermore, in the MAOMM, in its preferred conformation, the unsaturated portion (C=N) is situated in a spatial area which does not correspond exactly to the area occupied by Ar. The formal inversion of the atomic sequence C=NOCH2 of the MAOMM leads to a different type of group, the [(methyloxy)imino] methyl moiety (CH2ON=C, MOIMM), which, in the E configuration, appears to present greater steric and electronic analogies with an Ar, with respect to the MAOMM. On the basis of these observations, some completely aliphatic (E)-N-(3-amino-2-hydroxypropylidene) (alkyloxy)amino derivatives of type C (11a,b and 12a,b) were synthesized, the their beta-adrenergic properties were compared with those of the corresponding [(methyleneamino)oxy]methyl isomers of type B (19a,b and 20a,b). The similar beta-adrenergic properties of 11,12 and 19,20 evaluated in vitro both by radioligand binding assays and by functional tests on isolated preparations, are discussed on the basis of considerations regarding the spatial correspondences and electronic analogies between the MOIMM and the MAOMM.

  DOI：

  10.1021/jm00036a018

文献信息

• The [(Methyloxy)imino]methyl Moiety as a Bioisoster of Aryl. A Novel Class of Completely Aliphatic .beta.-Adrenergic Receptor Antagonists
  作者：Bruno Macchia、Aldo Balsamo、M. C. Breschi、Grazia Chiellini、Marco Macchia、Adriano Martinelli、Claudia Martini、Claudia Nardini、Susanna Nencetti

  DOI：10.1021/jm00036a018

  日期：1994.5

  Previous studies in the field of beta-adrenergic drugs had supported the hypothesis of the existence of a bioisosterism between the [(methyleneamino)oxy]methyl moiety (C=NOCH2, MAOMM) of type B beta-blocking drugs and the aryl (Ar) of type A beta-blocking agents. In the MAOMM, however, the carbon of the CH2 linked to the oximic oxygen possesses a hybridization (sp(3)) and a geometry different from those of the corresponding carbon of Ar which possesses an sp(2) hybridization. Furthermore, in the MAOMM, in its preferred conformation, the unsaturated portion (C=N) is situated in a spatial area which does not correspond exactly to the area occupied by Ar. The formal inversion of the atomic sequence C=NOCH2 of the MAOMM leads to a different type of group, the [(methyloxy)imino] methyl moiety (CH2ON=C, MOIMM), which, in the E configuration, appears to present greater steric and electronic analogies with an Ar, with respect to the MAOMM. On the basis of these observations, some completely aliphatic (E)-N-(3-amino-2-hydroxypropylidene) (alkyloxy)amino derivatives of type C (11a,b and 12a,b) were synthesized, the their beta-adrenergic properties were compared with those of the corresponding [(methyleneamino)oxy]methyl isomers of type B (19a,b and 20a,b). The similar beta-adrenergic properties of 11,12 and 19,20 evaluated in vitro both by radioligand binding assays and by functional tests on isolated preparations, are discussed on the basis of considerations regarding the spatial correspondences and electronic analogies between the MOIMM and the MAOMM.