ethyl 4-(3-nitrophenyl)-1,2-dihydro-6-methyl-2-oxopyrimidine-5-carboxylate | 893596-95-7

• 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: ethyl 4-(3-nitrophenyl)-1,2-dihydro-6-methyl-2-oxopyrimidine-5-carboxylate
• 英文别名: ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2-dihydropyrimidine-5-carboxylate；ethyl 6-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one-5-carboxylate；ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1H-pyrimidine-5-carboxylate
• CAS: 893596-95-7
• 化学式: C₁₄H₁₃N₃O₅
• 分子量: 303.274
• InChiKey: CJQVABMLSYBSPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(3-nitrophenyl)-1,2-dihydro-6-methyl-2-oxopyrimidine-5-carboxylate 、 二苯基碘三氟甲烷磺酸盐 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 以61%的产率得到ethyl 4-methyl-6-(3-nitrophenyl)-2-phenoxypyrimidine-5-carboxylate
  参考文献：
  名称：

  Direct metal-free O-arylation of Biginelli 4-aryl-6-methyl-pyrimidine-2(1H)-one derivatives using diaryliodonium salts

  摘要：

  4-Aryl-6-methyl-pyrimidine-2(1H)-one scaffolds of Biginelli type were subjected to C-O cross-coupling reactions using symmetrical diaryliodonium salts under transition metal-free conditions to afford 2-aryl-oxy pyrimidine derivatives in good to excellent yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.079
• 作为产物：
  描述：

  nifetepimine 在 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate 、 水 作用下， 以 乙腈 为溶剂， 反应 1.83h， 以85%的产率得到ethyl 4-(3-nitrophenyl)-1,2-dihydro-6-methyl-2-oxopyrimidine-5-carboxylate
  参考文献：
  名称：

  Novel and Chemoselective Dehydrogenation of 3,4-Dihydropyrimidin-2(1H)-ones with 1,4-Bis(triphenylphosphonium)-2-butene Peroxodisulfate

  摘要：

  3,4-二氢嘧啶-2(1H)-酮在1,4-双(三苯基膦)-2-丁烯过硫酸盐水溶液乙腈中处理下，短时间内高效转化为相应的嘧啶-2(1H)-酮，产率很高。该试剂还能在其他可氧化官能团的存在下实现3,4-二氢嘧啶的选择性氧化。

  DOI：

  10.5012/bkcs.2013.34.6.1751

文献信息

• A novel combination of (diacetoxyiodo)benzene and tert-butylhydroperoxide for the facile oxidative dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones
  作者：Nandkishor N. Karade、Sumit V. Gampawar、Jeevan M. Kondre、Girdharilal B. Tiwari

  DOI：10.1016/j.tetlet.2008.09.045

  日期：2008.11

  A clean and efficient oxidative dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones to 1,2-dihydropyrimidines has been achieved through a novel combination of (diacetoxyiodo)benzene and tert-butylhydroperoxide in CH2Cl2.

  通过在CH 2 Cl 2中将（diacetoxyiodo ）苯和叔丁基氢过氧化物进行新颖的结合，已实现了3,4-dihydropyrimidin-2（1 H）-ones的干净高效氧化脱氢成1,2-dihydropyrimidines 。
• Novel and Chemoselective Dehydrogenation of 3,4-Dihydropyrimidin-2(1H)-ones with 1,4-Bis(triphenylphosphonium)-2-butene Peroxodisulfate
  作者：Maryam Gorjizadeh

  DOI：10.5012/bkcs.2013.34.6.1751

  日期：2013.6.20

  3,4-Dihydropyrimidin-2(1H)-ones were efficiently converted into the corresponding pyrimidin-2(1H)-ones in high yields within a short period of time on treatment with aqueous acetonitrile using 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate. Chemoselective oxidation of 3,4-dihydropyrimidin in the presence of other oxidizable functional groups was also achieved by this reagent.

  3,4-二氢嘧啶-2(1H)-酮在1,4-双(三苯基膦)-2-丁烯过硫酸盐水溶液乙腈中处理下，短时间内高效转化为相应的嘧啶-2(1H)-酮，产率很高。该试剂还能在其他可氧化官能团的存在下实现3,4-二氢嘧啶的选择性氧化。
• An efficient and rapid dehydrogenation of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones (DHPMs) using CAN/HCl
  作者：Hitendra N. Karade、Jyotiranjan Acharya、Mahabir Parshad Kaushik

  DOI：10.1016/j.tetlet.2012.08.017

  日期：2012.10

  An efficient and operationally simple method for the dehydrogenation of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones (DHPMs) has been developed using CAN/HCl. (C) 2012 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed dehydrogenation of dihydro-heterocycles using isoprene as the hydrogen acceptor without oxidants
  作者：Xiao-Jun Liu、Wen-Peng Wang、Cong-De Huo、Xi-Cun Wang、Zheng-Jun Quan

  DOI：10.1039/c6cy02038k

  日期：——

  efficient and general method for Pd-catalyzed dehydrogenative aromatization of dihydro-heteroatom compounds without external O2 and H2 is first described. The protocol firstly uses isoprene as a hydrogen acceptor. Various dihydro-heterocycles including dihydropyrimidinones, dihydropyrimidines and dihydropyridines can be dehydrogenated to produce the corresponding aromatic heterocyclic compounds.

  首先描述了在没有外部O 2和H 2的情况下，Pd催化二氢杂原子化合物进行脱氢芳构化的有效方法。该方案首先使用异戊二烯作为氢受体。包括二氢嘧啶酮，二氢嘧啶和二氢吡啶在内的各种二氢杂环可被脱氢以产生相应的芳族杂环化合物。
• Direct metal-free O-arylation of Biginelli 4-aryl-6-methyl-pyrimidine-2(1H)-one derivatives using diaryliodonium salts
  作者：Prerana B. Thorat、Nitin A. Waghmode、Nandkishor N. Karade

  DOI：10.1016/j.tetlet.2014.08.079

  日期：2014.10

  4-Aryl-6-methyl-pyrimidine-2(1H)-one scaffolds of Biginelli type were subjected to C-O cross-coupling reactions using symmetrical diaryliodonium salts under transition metal-free conditions to afford 2-aryl-oxy pyrimidine derivatives in good to excellent yields. (C) 2014 Elsevier Ltd. All rights reserved.