Ethyl Ester of 4,6-Diphenyl-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic Acid | 34906-29-1

• 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 Ester of 4,6-Diphenyl-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic Acid
• 英文别名: ethyl 1,2-dihydro-2-oxo-4,6-diphenylpyrimidine-5-carboxylate；ethyl 2-oxo-4,6-diphenyl-1H-pyrimidine-5-carboxylate；ethyl 4,6-diphenylpyrimidin-2(1H)-one-5-carboxylate；2-oxo-4,6-diphenyl-1,2-dihydro-pyrimidine-5-carboxylic acid ethyl ester
• CAS: 34906-29-1
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: MOMNZZYQWWJGJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl Ester of 4,6-Diphenyl-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic Acid 在 caesium carbonate 、 lithium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 4-[4-[(5-ethoxycarbonyl-2-oxo-4,6-diphenyl-pyrimidin-1-yl)methyl]phenyl]-2-hydroxy-4-oxo-but-2-enoic acid
  参考文献：
  名称：

  Synthesis of dihydropyrimidine α,γ-diketobutanoic acid derivatives targeting HIV integrase

  摘要：

  The synthesis and antiviral evaluation of a series of dihydropyrimidinone and thiopyrimidine derivatives bearing aryl alpha, gamma-diketobutanoic acid moiety are described using the Biginelli multicomponent reaction as key step. The most active among 20 synthesized novel compounds were 4c, 4d and 5b, which possess nanomolar HIV-1 integrase (IN) stand transfer (ST) inhibition activities. In order to understand their mode of interactions within the IN active site, we docked all the compounds into the previously reported X-ray crystal structure of IN. We observed that compounds 4c, 4d and 5b occupied an area close to the two catalytic Mg2+ ions surrounded by their chelating triad (E221, D128 and D185), DC16, Y212 and the beta-diketo acid moiety of 4c, 4d and 5b chelating Mg2+. As those compounds lack anti-HIV activities in cell, their prodrugs were synthetized. The prodrug 4c' exhibited an anti-HIV activity of 0.19 mu M in primary human lymphocytes with some cytotoxicity. All together, these results indicate that the new analogs potentially interact within the catalytic site with highly conserved residues important for IN catalytic activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.015
• 作为产物：
  描述：

  ethyl 1-methyl-4,6-diphenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 五氯化磷 作用下， 以 三氯氧磷 为溶剂， 反应 4.0h， 以45%的产率得到Ethyl Ester of 4,6-Diphenyl-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic Acid
  参考文献：
  名称：

  Electrochemical reduction of hydrogenated 2-pyrimidones on a graphite electrode

  摘要：

  DOI：

  10.1007/bf00505910

文献信息

• Oxidative transformation of thiols to disulfides promoted by activated carbon–air system
  作者：Masahiko Hayashi、Ken-ichi Okunaga、Shunsuke Nishida、Kenjiro Kawamura、Kazuo Eda

  DOI：10.1016/j.tetlet.2010.10.070

  日期：2010.12

  Efficient oxidative transformation of thiols to disulfides took place in the presence of activated carbon under an oxygen (or air) atmosphere. The present oxidation method is available not only for a variety of thiols such as simple aromatic and aliphatic thiols but also for 3,4-dihydropyrimidin-2(1H)-thiones and N-Boc-l-cysteine.

  在氧气（或空气）气氛下，在存在活性炭的情况下，硫醇进行了有效的氧化转化为二硫化物。本氧化方法不仅可用于多种硫醇，例如简单的芳族和脂族硫醇，而且可用于3,4-二氢嘧啶-2（1 H）-硫酮和N- Boc- 1-半胱氨酸。
• Facile Synthesis of Chiral Cyclic Ureas through Hydrogenation of 2-Hydroxypyrimidine/Pyrimidin-2(1<i>H</i> )-one Tautomers
  作者：Guang-Shou Feng、Mu-Wang Chen、Lei Shi、Yong-Gui Zhou

  DOI：10.1002/anie.201801485

  日期：2018.5.14

  A facile access to optically active cyclic ureas was developed through palladium‐catalyzed asymmetric hydrogenation of pyrimidines containing tautomeric hydroxy group with up to 99 % ee. Mechanistic studies indicated that reaction pathway proceed through hydrogenation of C=N of the oxo tautomer pyrimidin‐2(1H)‐one, acid‐catalyzed isomerization of enamine–imine, and hydrogenation of imine pathway. In

  通过钯催化不对称氢化的嘧啶类化合物，可以容易地获得旋光性环状脲，其中嘧啶类的互变异构羟基含量高达ee的99％。机理研究表明，反应途径是通过羰基互变异构体嘧啶2（1 H）-1的C = N氢化，烯胺-亚胺的酸催化异构化和亚胺途径的氢化而进行的。此外，手性环状脲很容易转化为有用的手性1,3-二胺和硫脲衍生物，而不会降低光学纯度。
• Photochemical Preparation of Pyrimidin-2(1<i>H</i>)-ones by Rhenium(I) Complexes with Visible Light
  作者：Qiang Liu、Ya-Nan Li、Hui-Hui Zhang、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/jo102062u

  日期：2011.3.4

  irradiation (λ > 400 nm) of rhenium(I) complexes (P1−P4), a photochemical conversion from 3,4-dihydropyrimidin-2(1H)-ones to pyrimidin-2(1H)-ones at room temperature has been achieved with good to excellent yields in CH3CN−H2O solution containing CCl4 and K2CO3. Luminescence quenching study and product analysis reveal that photoinduced electron transfer between rhenium(I) complex P and 3,4-dihydropyrimidin-2(1H)-ones

  与铼的可见光照射（λ> 400nm）的（I）配合物（P1 - P4）由3,4-二氢嘧啶2，光化学转化（1 ħ） -酮向嘧啶-2-（1 ħ） -酮在在含有CCl 4和K 2 CO 3的CH 3 CN-H 2 O溶液中，室温可以达到良好或极好的收率。发光猝灭研究和产物分析表明rh（I）配合物P和3,4-dihydropyrimidin-2（1 H）-ones之间的光诱导电子转移在初始事件中起重要作用。
• Interrogation of 2,2′-Bipyrimidines as Low-Potential Two-Electron Electrolytes
  作者：Jeremy D. Griffin、Adam R. Pancoast、Matthew S. Sigman

  DOI：10.1021/jacs.0c11267

  日期：2021.1.20

  demonstrating the propensity of nitrogen-containing heterocycles to undergo multielectron reduction at low potentials, we focused on the development of a novel electrolyte scaffold based upon a 2,2'-bipyrimidine skeleton. This scaffold is capable of storing two electrons per molecule while also exhibiting a low (∼-2.0 V vs Fc/Fc+) reduction potential. A library of 24 potential bipyrimidine anolytes were

  随着可再生能源的利用不断扩大，对氧化还原液流电池（RFB）等新型电网储能技术的需求将变得至关重要。最终，RFB 的能量密度将取决于各个电解质的氧化还原电位、它们的溶解度以及每个分子存储的电子数量。先前的文献报道证明了含氮杂环在低电位下发生多电子还原的倾向，我们专注于开发基于2,2'-联嘧啶骨架的新型电解质支架。该支架能够每个分子存储两个电子，同时还表现出较低的还原电位（~-2.0 V vs Fc/Fc+）。合成并系统评估了 24 种潜在联嘧啶阳极电解液的库，以通过计算评估揭示结构-功能关系。通过对这些关系的分析，发现在还原态下破坏系统平面性的空间相互作用可能是导致某些阳极电解液更高水平降解的原因。最终确定主要分解途径是溶剂对二价阴离子的质子化，这可以通过电化学或化学氧化来逆转。为了验证应变诱导分解的假设，合成并评估了两种具有最小空间阻碍的新电解质，并发现它们确实比其空间位阻对应物表现出更高的稳定性。
• Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones through Organocatalytic Transfer Hydrogenation of 2-Hydroxypyrimidines
  作者：Fan-Jie Meng、Lei Shi、Guang-Shou Feng、Lei Sun、Yong-Gui Zhou

  DOI：10.1021/acs.joc.8b03128

  日期：2019.4.5

  acid-catalyzed transfer hydrogenation of 2-hydroxypyrimidines has been successfully realized using Hantzsch ester or dihydrophenanthridine as the hydrogen source, furnishing the chiral 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with excellent yields and enantioselectivities of ≤99%. Notably, a novel kind of chiral DHPMs with an alkyl stereogenic center can be prepared through highly chemoselective transfer hydrogenation

  以Hantzsch酯或二氢菲啶为氢源，成功地实现了2-羟基嘧啶的手性磷酸催化转移氢化，为手性3,4-二氢嘧啶-2（1 H）-one（DHPMs）提供了优异的收率和对映体选择性。 ≤99％。值得注意的是，可以通过高度化学选择性的转移氢化来制备具有烷基立体生成中心的新型手性DHPM。