2-phenyl-6-propyl-4(3H)-pyrimidinone | 14727-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-phenyl-6-propyl-4(3H)-pyrimidinone
• 英文别名: 2-phenyl-6-propylpyrimidin-4(3H)-one；4-Oxo-6-propyl-2-phenyl-3,4-dihydro-pyrimidin；2-phenyl-6-propyl-3H-pyrimidin-4-one；2-Phenyl-6-propyl-3,4-dihydropyrimidin-4-one；2-phenyl-4-propyl-1H-pyrimidin-6-one
• CAS: 14727-24-3
• 化学式: C₁₃H₁₄N₂O
• mdl: MFCD12137508
• 分子量: 214.267
• InChiKey: KRSOVLHLLUQZRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-6-propyl-4(3H)-pyrimidinone 在 palladium on activated charcoal ammonium hydroxide 、 氢气 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2-苯基-4-丙基嘧啶
  参考文献：
  名称：

  Sakamoto, Takao; Sakasai, Takeji; Yoshizawa, Hiroshi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 12, p. 4554 - 4560

  摘要：

  DOI：
• 作为产物：
  描述：

  苄脒盐酸盐 、 (E)-1,1,1-trichloro-4-methoxyhept-3-en-2-one 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以87%的产率得到2-phenyl-6-propyl-4(3H)-pyrimidinone
  参考文献：
  名称：

  5-和 6-取代的 2-Phenyl-3H-pyrimidin-4-ones 的便捷合成

  摘要：

  通过 4-alkoxy-1,1,1-trichloroalk-3-en- 缩合合成 5-和 6-取代的 2-苯基-3 H-嘧啶-4-酮的简单方便的一锅法描述了与苯甲脒盐酸盐的 2-ones。

  DOI：

  10.1055/s-2008-1032032

文献信息

• Regiospecific Bromination of 2-Phenyl-3<i>H</i>-pyrimidin-4-ones
  作者：Nilo Zanatta、Leonardo Fantinel、Liana Fernandes、Ana Wouters、Helio Bonacorso、Marcos Martins

  DOI：10.1055/s-0028-1083178

  日期：——

  Three methods for the regiospecific bromination of 2-phenyl-3H-pyrimidin-4-ones are presented: bromination of the 5-position of the pyrimidine ring, bromination of the 6-benzylic position and simultaneous bromination of both the 5-position of the pyrimidine ring and 6-benzylic position. Reactions were carried out using simple protocols and the brominated pyrimidines were obtained in good yields.

  本文介绍了 3 种 2-苯基-3H-嘧啶-4-酮的特异性溴化方法：嘧啶环 5 位溴化、6-苄基位溴化以及嘧啶环 5 位和 6-苄基位同时溴化。反应采用简单的方案进行，溴化嘧啶的收率很高。
• Synthesis and Biological Evaluation of Novel Sigma-1 Receptor Antagonists Based on Pyrimidine Scaffold As Agents for Treating Neuropathic Pain
  作者：Yu Lan、Yin Chen、Xudong Cao、Juecheng Zhang、Jie Wang、Xiangqing Xu、Yinli Qiu、Tan Zhang、Xin Liu、Bi-Feng Liu、Guisen Zhang

  DOI：10.1021/jm501207r

  日期：2014.12.26

  The discovery and synthesis of a new series of pyrimidines as potent sigma-1 receptor (sigma R-1) antagonists, associated with pharmacological antineuropathic pain activity, are the focus of this article. The new compounds were evaluated in vitro in sigma-1 and sigma-2 receptor binding assays. The nature of the pyrimidine scaffold was crucial for activity, and a basic amine was shown to be necessary according to the known pharmacophoric model. The most promising derivative was 5-chloro-2-(4-chlorophenyl)-4-methyl-6-(3-(piperidin-1-yl)propoxy)pyrimidine (137), which exhibited a high binding affinity to sigma R-1 receptor (K-i sigma(1) = 1.06 nM) and good sigma-1/2 selectivity (1344-fold). In in vivo tests, compound 137 exerted dose-dependent antinociceptive effects in mice formalin model and rats CCI models of neuropathic pain. In addition, no motor impairments were found in rotarod tests; acceptable pharmacokinetic properties were also noted. These data suggest compound 137 may constitute a novel class of drugs for the treatment of neuropathic pain.
• SAKAMOTO, TAKAO;SAKASAI, TAKEJI;YOSHIZAWA, HIROSHI;TANJI, KEN-ICHI;NISHIM+, CHEM. AND PHARM. BULL., 1983, 31, N 12, 4554-4560
  作者：SAKAMOTO, TAKAO、SAKASAI, TAKEJI、YOSHIZAWA, HIROSHI、TANJI, KEN-ICHI、NISHIM+

  DOI：——

  日期：——
• Sakamoto, Takao; Sakasai, Takeji; Yoshizawa, Hiroshi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 12, p. 4554 - 4560
  作者：Sakamoto, Takao、Sakasai, Takeji、Yoshizawa, Hiroshi、Tanji, Ken-Ichi、Nishimura, Sumiko、Yamanaka, Hiroshi

  DOI：——

  日期：——
• A Convenient Synthesis of 5- and 6-Substituted 2-Phenyl-3<i>H</i>-pyrimidin-4-ones
  作者：Nilo Zanatta、Leonardo Fantinel、Rogério Lourega、Helio Bonacorso、Marcos Martins

  DOI：10.1055/s-2008-1032032

  日期：2008.2

  A simple and convenient one-pot procedure for the synthesis of 5- and 6-substituted 2-phenyl-3 H-pyrimidin-4-ones by the condensation of 4-alkoxy-1,1,1-trichloroalk-3-en-2-ones with benz-amidine hydrochloride is described.

  通过 4-alkoxy-1,1,1-trichloroalk-3-en- 缩合合成 5-和 6-取代的 2-苯基-3 H-嘧啶-4-酮的简单方便的一锅法描述了与苯甲脒盐酸盐的 2-ones。