5-ethoxycarbonyl-6-methyl-3-acetyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one | 123043-99-2

• 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: 5-ethoxycarbonyl-6-methyl-3-acetyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 3-acetyl-5-ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2-one；Ethyl 3-acetyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；ethyl 3-acetyl-6-methyl-2-oxo-4-phenyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 123043-99-2
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: FMBPKHVACPZMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethoxycarbonyl-6-methyl-3-acetyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one 生成 (S)-3-Acetyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Separation of enantiomers of 4-aryldihydropyrimidines by direct enantioselective HPLC. A critical comparison of chiral stationary phases

  摘要：

  The separation of the enantiomers of 29 racemic 4-aryldihydropyrimidine-5-carboxylates (DHPMs), aza-analogs of nifedipine-type dihydropyridine calcium channel modulators, was evaluated in direct enantioselective HPLC, employing the following commercially available chiral stationary phases (CSPs): Chiralcel OD-H, ChiraDex, Chirobiotic V and T, and Whelk-O1. In addition, a 1,2-diphenyl-1,2-diaminoethane based CSP and two quinine carbamate based chiral ion exchangers were also employed. For all 29 DHPMs separation of individual enantiomers could be achieved with at least one CSP with alpha-values ranging from 1.10 to 8.67. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00214-0
• 作为产物：
  描述：

  5-ethoxycarbonyl-6-methyl-1,3-diacetyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one 在 氨 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到乙酰胺
  参考文献：
  名称：

  N 1，N 3-二酰基-3,4-二氢嘧啶-2（1 H）-ones：中性酰基转移试剂

  摘要：

  易于获得的N 1，N 3-二酰基3,4-二氢嘧啶-2（1 H）-一有效地酰化氨，伯胺和仲胺，从而以良好或优异的收率提供伯，仲和叔酰胺。通过在中性介质中进行反应，易于分离产物，回收无害副产物和进行转化的化学选择性，证明了该方法的广泛适用性。

  DOI：

  10.1016/j.tet.2009.10.037

文献信息

• A mild and practical method for the regioselective synthesis of N-acylated 3,4-dihydropyrimidin-2-ones. New acyl transfer reagents
  作者：Kamaljit Singh、Sukhdeep Singh

  DOI：10.1016/j.tetlet.2006.09.039

  日期：2006.11

  The treatment of 3,4-dihydropyrimidin-2-ones with n-BuLi at −78 °C, followed by quenching with various electrophiles furnished N3-substituted derivatives, regioselectively. Further, N1,N3-diacyl derivatives were found to transfer N1-acyl groups to nucleophilic sites.

  在-78°C下用正丁基锂处理3,4-二氢嘧啶-2-酮，然后用区域选择性选择性提供的N 3取代衍生物的各种亲电试剂淬灭。此外，发现N 1，N 3-二酰基衍生物将N 1-酰基转移至亲核位点。
• Synthesis of Acetylated Dihydropyrimidine Analogues Under Solvent Free Conditions and their Evaluation as Calcium Channel Blockers
  作者：BHAWANA SATI、ELLAMMA ELLAMMA、HEMLATA SATI、L.V.G. NARGUND、SOMILA KHAIDEM、PRAKASH CHANDRA BHATT、SARLA SAKLANI

  DOI：10.13005/ojc/280259

  日期：2012.6.18

  by SnCl 2 .2H 2 O affords eight different substituted 3,4-dihydropyrimidine ones/ thiones. Further we prepared acetylated 3,4-dihydropyrimidine ones/thiones, on treatment of 3,4-dihydropyrimidine ones/thiones with acetic anhydride using zinc chloride as a catalyst. Calcium channel blocker activity shows that synthesized compounds have moderate activity.

  通过SnCl 2 .2H 2 O将乙酰乙酸乙酯与各种对位和邻位取代的醛以及脲或硫脲进行一锅缩合，得到八种不同的3,4-二氢嘧啶基/硫酮。进一步，在使用氯化锌作为催化剂，用乙酸酐处理3,4-二氢嘧啶基/硫酮的过程中，我们制备了乙酰化的3,4-二氢嘧啶基/硫酮。钙通道阻滞剂活性表明合成的化合物具有中等活性。
• High-Throughput Synthesis of <i>N</i>3-Acylated Dihydropyrimidines Combining Microwave-Assisted Synthesis and Scavenging Techniques
  作者：Doris Dallinger、Nikolay Yu. Gorobets、C. Oliver Kappe

  DOI：10.1021/ol034085v

  日期：2003.4.1

  The solution-phase synthesis of N3-acylated dihydropyrimidines was achieved utilizing microwave flash heating both in the synthesis (acylation) and purification (scavenging) steps. Quenching times for excess anhydrides using polystyrene or silica-supported diamine sequestration reagents were reduced from several hours to minutes utilizing microwave irradiation. The use of water as sequestration agent, coupled with an efficient solid-phase extraction workup technique allowed the rapid generation of a 20-member library of N3-acylated dihydropyrimidines.
• Kappe, Christian Oliver; Roschger, Peter, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 55 - 64
  作者：Kappe, Christian Oliver、Roschger, Peter

  DOI：——

  日期：——
• 3-N-Acylation of 5-Ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2-one
  作者：M. A. Kolosov、V. D. Orlov

  DOI：10.1007/s10593-005-0139-y

  日期：2005.2