4-phenyl-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione | 20946-01-4

• 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-phenyl-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione
• 英文别名: 4-phenyl-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione；1-Phenyl-2,4-diazafluoren-3,9-dion
• CAS: 20946-01-4
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: ISEKSXKHQRZFJA-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C (decomp)
• 沸点：
  490.8±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 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：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以71%的产率得到4-phenyl-1H-indeno[1,2-d]pyrimidine-2,5-dione
  参考文献：
  名称：

  Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate

  摘要：

  Ceric ammonium nitrate (CAN) has been explored for the regioselective oxidation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). Interestingly, we obtained ethyl 2,4-dioxo-6-phenyl-tetrahydropyrimidin-5-carboxylates as the major products during the oxidation of DHPMs by CAN/AcOH at 80 degrees C. The reaction afforded a mixture of products while employing CAN in organic solvents without additives. However, the regioselective dehydrogenated product, ethyl 6-methyl-4-aryl(alkyl)-pyrimidin-2(1H)-one-5-carboxylate was obtained by performing the reaction with NaHCO3. The single crystal X-ray crystallography of ethyl 6-methyl-4-(2-phenyl)-pyrimidin-2(1H)-one-5-carboxylate revealed that the oxidized product existed in amidic form rather than aromatized enol form of pyrimidines. The efficiency of the present protocol enabled the synthesis of structurally diverse pyrimidines in moderate to good yields under milder reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.063
• 作为产物：
  描述：

  尿素 、 2-(苯基亚甲基)茚-1,3-二酮 以 溶剂黄146 为溶剂， 反应 0.42h， 以65%的产率得到4-phenyl-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione
  参考文献：
  名称：

  Ali, Mohamed I.; El-Fotooh, Abou; Hamman, G., Phosphorus and Sulfur and the Related Elements, 1988, vol. 39, p. 211 - 216

  摘要：

  DOI：

文献信息

• Design, Synthesis, Characterization, and Antimicrobial Activity of Biginelli Products of Indandione
  作者：Vijay V. Dabholkar、Sunil R. Patil、Rajesh V. Pandey

  DOI：10.1002/jhet.860

  日期：2012.7

  method has been developed for the synthesis of 4‐(substituted phenyl)‐3,4‐dihydro‐1H‐indeno [1,2‐d] pyrimidine‐2,5‐dione (5) and 4‐(substituted phenyl)‐2‐thioxo‐1,2,3,4‐tetrahydroindeno [1,2‐d] pyrimidine‐5‐one (6), by a one‐pot three component cyclocondensation reaction of 1,3 dicarbonyl compound (Indandione) (1), aromatic aldehyde (2), and urea/thiourea (3/4) using catalytic amount of conc. HCl in

  已开发出一种简单有效的方法来合成4-（取代的苯基）-3,4-二氢-1H-茚并[1,2-d]嘧啶-2,5-二酮（5）和4-（取代的）（1），3-二羰基化合物（茚满二酮）的一锅三组分环缩合反应生成苯基）-2-硫代-2-2,3,4-四氢茚并[1,2-d]嘧啶-5- （6）（1），芳香醛（2）和尿素/硫脲（3/4），使用催化量的浓 在回流乙醇中的HCl。筛选代表性样品对革兰氏阴性菌，大肠杆菌和铜绿假单胞菌以及革兰氏阳性菌，金黄色葡萄球菌和白喉C杆菌的抗菌活性使用圆盘扩散法。产物的结构通过IR，1 H，13 C NMR和元素分析确认。
• COMPOUNDS USEFUL FOR TREATING INJURIES FROM WARFARE AGENTS
  申请人：Wu Xinyuan

  公开号：US20150352115A1

  公开（公告）日：2015-12-10

  Compounds and compositions for treating disorders related to TRPA1 are described herein.

  本文描述了用于治疗与TRPA1相关的疾病的化合物和组合物。
• An unusual oxidation–dealkylation of 3,4-dihydropyrimidin-2(1H)-ones mediated by Co(NO3)2·6H2O/K2S2O8 in aqueous acetonitrile
  作者：Pachaiyappan Shanmugam、Paramasivan T. Perumal

  DOI：10.1016/j.tet.2006.11.010

  日期：2007.1

  4-Aryl-6-methyl-3,4-dihydropyrimidin-2(1H)-one (DHPM) scaffolds of Biginelli type were oxidized using Co(II)/S2O82- and the reaction afforded 6-unsubstituted pyrimidin-2(1H)-ones through an unprecedented dealkylation process. 4-Alkyl DHPMs under similar conditions afforded yet another unusual product, ethyl tetrahydropyrimidin-2,4(1H,3H)-dione-5-carboxylate. (c) 2006 Elsevier Ltd. All rights reserved.
• Tricyclic 3,4-dihydropyrimidine-2-thione derivatives as potent TRPA1 antagonists
  作者：Harrie J.M. Gijsen、Didier Berthelot、Michel A.J. De Cleyn、Ivo Geuens、Bert Brône、Marc Mercken

  DOI：10.1016/j.bmcl.2011.12.068

  日期：2012.1

  The transient receptor potential A1 (TRPA1) channel has been implicated in a number of inflammatory and nociceptive processes, and antagonists of the TRPA1 receptor could offer a potential treatment for conditions such as inflammatory or neuropathic pain, airway disorders, and itch. In a high throughput screen aimed at the identification of TRPA1 antagonists, 4-phenyl-2-thioxo-1,2,3,4-tetrahydroindeno[1,2-d]pyrimidin-5-one (1) was identified as a potent TRPA1 receptor antagonist. A series of analogous tricyclic 3,4-dihydropyrimidine-2-thiones has been prepared via the multi-component Biginelli reaction and subsequent derivatization. This has led to TRPA1 antagonists with potencies around 10 nM for both rat and human derived TRPA1 receptors. The activity was shown to reside exclusively in the 4R-enantiomers. (C) 2011 Elsevier Ltd. All rights reserved.
• 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：——