1,2-二氢-4-甲基-2-氧代-6-苯基-5-嘧啶羧酸乙酯 | 69207-36-9

• 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: 1,2-二氢-4-甲基-2-氧代-6-苯基-5-嘧啶羧酸乙酯
• 英文名称: ethyl 6-methyl-4-phenylpyrimidin-2(1H)-one-5-carboxylate
• 英文别名: ethyl 6-methyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxylate；ethyl 6-methyl-2-oxo-4-phenyl-1H-pyrimidine-5-carboxylate
• CAS: 69207-36-9
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: SWIRDXKNRHFQJR-UHFFFAOYSA-N

物化性质

• 熔点：
  192-194°C
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 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：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1,2-二氢-4-甲基-2-氧代-6-苯基-5-嘧啶羧酸乙酯 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2-(4-hydroxyphenylamino)-4-methyl-6-phenylpyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity

  摘要：

  A series of pyrimidine derivatives bearing amine substituents at C-2 position were obtained from Biginelli 3,4-dihydropyrimidin-2(1H)-ones and the effect of structural variation on anti-TB activity against Mycobacterium tuberculosis H(37)Rv strain and antiviral activity in a series of cell cultures was evaluated. While the compounds were found to possess structure dependent cytostatic activity, these were not found to be efficient inhibitors of M. tuberculosis nor did they inhibit a broad variety of DNA or RNA viruses in cell culture. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.010
• 作为产物：
  描述：

  2-甲氧基-4-甲基-6-苯基嘧啶-5-羧酸乙酯 在 吡啶盐酸盐 作用下， 反应 0.5h， 以45%的产率得到1,2-二氢-4-甲基-2-氧代-6-苯基-5-嘧啶羧酸乙酯
  参考文献：
  名称：

  Synthesis and Aromatization of Dihydropyrimidines Structurally Related to Calcium Channel Modulators of the Nifedipine-Type

  摘要：

  DOI：

  10.3987/com-97-7931

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 。
• Oxidation of Biginelli Reaction Products: Synthesis of 2-Unsubstituted 1,4-Dihydropyrimidines, Pyrimidines, and 2-Hydroxypyrimidines
  作者：Hyunik Shin、Sam Kim、Bo Choi、Jae Lee、Ki Lee、Tae Lee、Young Kim

  DOI：10.1055/s-0028-1087920

  日期：2009.3

  from the Biginelli product, dihydropyrimidin-2(1H)-thiones in two steps: Oxidation of dihydropyrimidin-2(1H)-thiones using oxone on wet alumina or hydrogen peroxide in the presence of catalytic amount of vanadyl sulfate provided 1,4-di-hydropyrimidine, which was further oxidized to 2-unsubstituted pyrimidines by the treatment of KMnO 4 . Oxidation of dihydropyrimidin-2(1H)-ones by KMnO 4 formed 2-hydroxypyrimidine

  我们设计了一条从 Biginelli 产物二氢嘧啶-2(1H)-硫酮获得 2-未取代嘧啶衍生物的新途径，分两步进行： 在湿氧化铝或过氧化氢存在下使用 oxone 氧化二氢嘧啶-2(1H)-硫酮催化量的硫酸氧钒提供1,4-二氢嘧啶，通过KMnO 4 的处理将其进一步氧化为2-未取代的嘧啶。KMnO 4 氧化二氢嘧啶-2(1H)-酮以优异的产率形成2-羟基嘧啶，而尝试通过KMnO 4 直接脱硫二氢嘧啶-2(1H)-硫酮导致形成2-羟基嘧啶，相同的产物由二氢嘧啶-2(1H)-one氧化得到。
• 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。
• 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。
• Palladium(II) Catalyzed Suzuki/Sonogashira Cross-Coupling Reactions of Sulfonates: An Efficient Approach to C2-Functionalized Pyrimidines and Pyridines
  作者：Zheng-Jun Quan、Fu-Qiang Jing、Zhang Zhang、Yu-Xia Da、Xi-Cun Wang

  DOI：10.1002/ejoc.201300592

  日期：2013.11

  Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)2-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized

  嘧啶-2-基磺酸盐作为反应伙伴，可以从廉价的商业材料中轻松制备，并通过使用 Pd(OAc)2 催化的 Suzuki 和 Sonogashira 反应与芳基硼酸和末端炔烃有效交叉偶联。大量 C2 官能化的嘧啶已经以良好到极好的产率制备。还合成了 2-芳基吡啶和 2-(oct-1-ynyl) 吡啶。