4-(3-nitrophenyl)-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 4-(3-nitrophenyl)-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione
• 化学式: C₁₇H₁₁N₃O₄
• 分子量: 321.292
• InChiKey: MADAZCSFUNHSHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-茚满二酮 、 间硝基苯甲醛 、 尿素 在 四磷十氧化物 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以93%的产率得到4-(3-nitrophenyl)-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione
  参考文献：
  名称：

  An Efficient and Modified Biginelli-Type Synthesis of 3,4-Dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione Using Phosphorous Pentoxide

  摘要：

  A simple, clean and convenient one-pot method has been developed for the synthesis of 4-phenyl-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione and 4-phenyl-2-thioxo-1,2,3,4-tetrahydro-5H-indeno[1,2-d]pyrimidine-5-one by multicomponent condensation of 1,3-indanedione, aromatic aldehydes and urea/thiourea using phosphorus pentoxide in ethanol under reflux conditions. The simple workup procedure and moderate to good yields within short time are some important features of this protocol. The synthesized compounds have been interpreted on the basis of their spectroscopic data.

  DOI：

  10.1080/00397911.2014.947652

文献信息

• [EN] 3,4-DIHYDROPYRIMIDINE TRPA1 ANTAGONISTS<br/>[FR] ANTAGONISTES DES TRPA1 CONSTITUÉS PAR DES 3,4-DIHYDROPYRIMIDINES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2009147079A1

  公开（公告）日：2009-12-10

  The present invention is related to novel 3,4-dihydropyrimidine compounds of formula (I) having TRPA1 receptor antagonistic properties, pharmaceutical compositions comprising these compounds, chemical processes for preparing these compounds and their use in the treatment of diseases linked to the modulation of the TRPA1 receptors in animals, in particular humans.

  本发明涉及具有TRPA1受体拮抗性质的新型3,4-二氢嘧啶化合物（I）的药物组合物，包括这些化合物的化学制备过程以及它们在治疗与动物中TRPA1受体调节相关的疾病，特别是人类中的用途。
• Shanmugam, Pachaiyappan; Sabastein, Cruz; Perumal, Paramasivan T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 1, p. 135 - 140
  作者：Shanmugam, Pachaiyappan、Sabastein, Cruz、Perumal, Paramasivan T.

  DOI：——

  日期：——
• 3,4-DIHYDROPYRIMIDINE TRPA1 ANTAGONISTS
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP2300440B1

  公开（公告）日：2013-02-27
• An Efficient and Modified Biginelli-Type Synthesis of 3,4-Dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione Using Phosphorous Pentoxide
  作者：Poojali P. Warekar、Govind B. Kolekar、Madhukar B. Deshmukh、Prashant V. Anbhule

  DOI：10.1080/00397911.2014.947652

  日期：2014.12.17

  A simple, clean and convenient one-pot method has been developed for the synthesis of 4-phenyl-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione and 4-phenyl-2-thioxo-1,2,3,4-tetrahydro-5H-indeno[1,2-d]pyrimidine-5-one by multicomponent condensation of 1,3-indanedione, aromatic aldehydes and urea/thiourea using phosphorus pentoxide in ethanol under reflux conditions. The simple workup procedure and moderate to good yields within short time are some important features of this protocol. The synthesized compounds have been interpreted on the basis of their spectroscopic data.