6-(Dimethylaminomethylene)-2-cyclohexen-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(Dimethylaminomethylene)-2-cyclohexen-1-one
• 英文别名: 6-(dimethylaminomethylene)cyclohex-2-en-1-one；6-(dimethylaminomethylidene)cyclohex-2-en-1-one
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: KSNAGDSXEHQTGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-(Dimethylaminomethylene)-2-cyclohexen-1-one 、 肌酸 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 10.25h， 以62%的产率得到[(5,6-Dihydro-quinazolin-2-yl)-methyl-amino]-acetic acid
  参考文献：
  名称：

  Antiinflammatory agents: new series of N-substituted amino acids with complex pyrimidine structures endowed with antiphlogistic activity

  摘要：

  A series of N-methyl-N-pyrimidin-2-yl glycines 2a-e, having the pyrimidine ring fused with a cyclohexane [N-methyl-N-(5,6,7,8-tetrahydroquinazolin-2-yl)glycine], cyclohexene [N-methyl-N-(5,6-dihydroquinazolin-2-yl)glycine], 1,2,3,4-tetrahydronaphthalene [N-methyl-N-(5,6-dihydrobenzo[e]quinazolin-2-yl)glycine], benzopyrane [N-methyl-N-(5-phenyl-5H-[1]benzopyrano[4,3-d]pyrimidin-2-yl)glyci ne] and benzothiopyrane [N-methyl-N-(5H-[1]benzothiopyrano[4,3-d]pyrimidin-2-yl)glycine] ring, was prepared and tested for antiinflammatory activity. With the same purpose a number of N-5H-[1]benzopyrano[4,3-d]pyrimidin-2-yl substituted amino acids 3a-e, having a different chain length and branching were also synthesized and tested. All the described products 2 and 3 showed an appreciable antiphlogistic activity, particularly 2b and 2c.

  DOI：

  10.1016/s0014-827x(98)00109-8

文献信息

• NMR of enaminones. part 6—17O and13C NMR study of tautomerization in Schiff bases
  作者：Jin-Cong Zhuo

  DOI：10.1002/(sici)1097-458x(199904)37:4<259::aid-mrc442>3.0.co;2-6

  日期：1999.4

  13C and 17O NMR spectra are reported for three series of Schiff bases: 2‐(aminomethylene)cyclohexanones (1), salicylideneamines (2) and N‐(2‐hydroxy‐1‐naphthalenylmethylene)amines (3). The 13C and 17O NMR data show that Schiff bases 1 exist in ketoenamine form, 2 in enolimine form and 3 as an equilibrium mixture of both forms. The tautomeric composition of Schiff base 3 was estimated. Alkylamines slightly

  报告了三个系列席夫碱的 13C 和 17O NMR 光谱：2-（氨基亚甲基）环己酮（1）、水杨基胺（2）和 N-（2-羟基-1-萘基亚甲基）胺（3）。13C 和 17O NMR 数据表明席夫碱 1 以酮烯胺形式存在，2 以烯胺形式存在，3 作为两种形式的平衡混合物存在。估计了希夫碱 3 的互变异构组成。烷基胺略微偏向于酮烯胺形式；芳香胺有利于烯胺形式。在非极性溶剂中，随着温度的升高，互变异构平衡向烯胺形式转移。版权所有 © 1999 John Wiley & Sons, Ltd.
• Antiinflammatory agents: new series of N-substituted amino acids with complex pyrimidine structures endowed with antiphlogistic activity
  作者：Olga Bruno、Silvia Schenone、Angelo Ranise、Francesco Bondavalli、Walter Filippelli、Giuseppe Falcone、Giulia Motola、Filomena Mazzeo

  DOI：10.1016/s0014-827x(98)00109-8

  日期：1999.1

  A series of N-methyl-N-pyrimidin-2-yl glycines 2a-e, having the pyrimidine ring fused with a cyclohexane [N-methyl-N-(5,6,7,8-tetrahydroquinazolin-2-yl)glycine], cyclohexene [N-methyl-N-(5,6-dihydroquinazolin-2-yl)glycine], 1,2,3,4-tetrahydronaphthalene [N-methyl-N-(5,6-dihydrobenzo[e]quinazolin-2-yl)glycine], benzopyrane [N-methyl-N-(5-phenyl-5H-[1]benzopyrano[4,3-d]pyrimidin-2-yl)glyci ne] and benzothiopyrane [N-methyl-N-(5H-[1]benzothiopyrano[4,3-d]pyrimidin-2-yl)glycine] ring, was prepared and tested for antiinflammatory activity. With the same purpose a number of N-5H-[1]benzopyrano[4,3-d]pyrimidin-2-yl substituted amino acids 3a-e, having a different chain length and branching were also synthesized and tested. All the described products 2 and 3 showed an appreciable antiphlogistic activity, particularly 2b and 2c.