1,2,3,4-四氢-6-甲基-4-(4-硝基苯基)-2-氧代-5-嘧啶羧酸 | 356566-57-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1,2,3,4-四氢-6-甲基-4-(4-硝基苯基)-2-氧代-5-嘧啶羧酸
• 英文名称: 6-Methyl-4-(4-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid
• 英文别名: 6-Methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid；6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylic acid
• CAS: 356566-57-9
• 化学式: C₁₂H₁₁N₃O₅
• 分子量: 277.236
• InChiKey: JRAMDMCEIDFGMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  489.5±45.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢-6-甲基-4-(4-硝基苯基)-2-氧代-5-嘧啶羧酸 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-ethylsulfinylethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
  参考文献：
  名称：

  Identification and characterization of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones as inhibitors of the fatty acid transporter FATP4

  摘要：

  Several potent, cell permeable 4-aryl-dihydropyrimidinones have been identified as inhibitors of FATP4. Lipophilic ester substituents at the 5-position and substitution at the para-position (optimal groups being -NO2 and CF3) of the 4-aryl group led to active compounds. In two cases racemates were resolved and the S enantiomers shown to have higher potencies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.102
• 作为产物：
  描述：

  2-cyanoethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 以95%的产率得到1,2,3,4-四氢-6-甲基-4-(4-硝基苯基)-2-氧代-5-嘧啶羧酸
  参考文献：
  名称：

  Identification and characterization of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones as inhibitors of the fatty acid transporter FATP4

  摘要：

  Several potent, cell permeable 4-aryl-dihydropyrimidinones have been identified as inhibitors of FATP4. Lipophilic ester substituents at the 5-position and substitution at the para-position (optimal groups being -NO2 and CF3) of the 4-aryl group led to active compounds. In two cases racemates were resolved and the S enantiomers shown to have higher potencies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.102

文献信息

• 离子液体常温催化3,4-二氢嘧啶-2-酮类化合 物的合成方法
  申请人：盐城师范学院

  公开号：CN106632073B

  公开（公告）日：2019-06-14

  本发明公开了一种离子液体常温催化3，4‑二氢嘧啶‑2‑酮类化合物的合成方法。其技术关键是采用纳米硅负载的酸官能团的离子液体作为催化剂，乙醇作为反应介质，原料芳香醛、1，3‑二羰基化合物、脲素于常温、常压下反应得到目标产物。优点为：(1)原料来源广泛，制备方便；(2)催化剂催化效果好，分离简单，可循环使用、节能减排的效果明显；(3)反应在常温常压下进行，安全平稳，容易工业放大，是环境友好的化工过程。
• ENANTIOSELECTIVE SYNTHESIS OF DIHYDROPYRIMIDINONES AND HEXAHYDROPYRIMIDINONES
  申请人：Universitat de les Illes Balears

  公开号：EP3260446A1

  公开（公告）日：2017-12-27

  The present invention provides with a "one pot" easily scalable preparation process, or method to obtain enantiomerically enriched dihydropyrimidinones (DHPMs), in high yield and high enantiomeric purity, based on the concept of organocatalysis by a network of cooperative hydrogen bonds (NCHB). Said preparation process obtains enantiomerically enriched DHPMs without the use of metal-based catalysis and with the possibility of the recovery of the chiral organocatalyst comprising a NCHB used. The present invention also provides with new enantiomerically and diastereomerically enriched hexahydropyrimidinones (HHPMs), as well as a preparation process to obtain them also based on the concept of organocatalysis by a NCHB. Said preparation process obtains enantiomerically and diastereomerically enriched HHPMs without the use of metal-based catalysis and with the possibility of the recovery of the chiral organocatalyst comprising a NCHB used.

  本发明基于协同氢键网络（NCHB）有机催化的概念，提供了一种 "一锅式 "易扩展的制备工艺或方法，以高产率和高对映体纯度获得对映体富集的二氢嘧啶酮（DHPMs）。所述制备工艺无需使用金属催化，即可获得对映体富集的 DHPM，并有可能回收由所使用的 NCHB 组成的手性有机催化剂。本发明还提供了新的对映异构体和非对映异构体富集的六氢嘧啶酮（HHPMs），以及同样基于 NCHB 有机催化概念的获得它们的制备工艺。该制备工艺无需使用金属催化即可获得对映体和非对映异构体富集的六氢嘧啶酮（HHPMs），并有可能回收由所使用的 NCHB 组成的手性有机催化剂。
• Valverde, Maria Garcia; Dallinger, Doris; Kappe, C. Oliver, Synlett, 2001, # 6, p. 741 - 744
  作者：Valverde, Maria Garcia、Dallinger, Doris、Kappe, C. Oliver

  DOI：——

  日期：——
• [EN] NOVEL 2-OXO-1,2,3,4-TETRAHYDROPYRIMIDINES, BICYCLIC PYRIMIDINE DIONES AND IMIDAZOLIDINE-2,4-DIONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] NOUVELLES 2-OXO-1,2,3,4-TÉTRAHYDROPYRIMIDINES, PYRIMIDINE DIONES BICYCLIQUES ET IMIDAZOLIDINE-2,4-DIONES UTILES COMME INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE INDUCTIBLE
  申请人：KALYPSYS INC

  公开号：WO2007101213A2

  公开（公告）日：2007-09-07

  [EN] The present invention relates to novel 2-oxo-l,2,3,4-tetrahydropyrimidines, bicyclic pyrimidine diones and imidizolidine-2,4-diones and methods useful as inhibitors of nitric oxide synthase.
  [FR] La présente invention concerne de nouvelles 2-oxo-1,2,3,4-tétrahydropyrimidines, pyrimidine diones bicycliques et imidizolidine-2,4-diones et des procédés, utiles comme inhibiteurs de l'oxyde nitrique synthase.
• Identification and characterization of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones as inhibitors of the fatty acid transporter FATP4
  作者：Christopher Blackburn、Bing Guan、James Brown、Courtney Cullis、Stephen M. Condon、Tracy J. Jenkins、Stephane Peluso、Yingchun Ye、Ruth E. Gimeno、Sandhya Punreddy、Ying Sun、Hui Wu、Brian Hubbard、Virendar Kaushik、Peter Tummino、Praveen Sanchetti、Dong Yu Sun、Tom Daniels、Effie Tozzo、Suresh K. Balani、Prakash Raman

  DOI：10.1016/j.bmcl.2006.03.102

  日期：2006.7

  Several potent, cell permeable 4-aryl-dihydropyrimidinones have been identified as inhibitors of FATP4. Lipophilic ester substituents at the 5-position and substitution at the para-position (optimal groups being -NO2 and CF3) of the 4-aryl group led to active compounds. In two cases racemates were resolved and the S enantiomers shown to have higher potencies. (c) 2006 Elsevier Ltd. All rights reserved.