ethyl 3-acetyl-6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 111535-64-9

• 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 3-acetyl-6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 3-acetyl-6-methyl-4-phenyl-3,4-dihydropyrimidine-2(1H)thione-5-carboxylate；Ethyl 3-acetyl-6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；ethyl 3-acetyl-6-methyl-4-phenyl-2-sulfanylidene-1,4-dihydropyrimidine-5-carboxylate
• CAS: 111535-64-9
• 化学式: C₁₆H₁₈N₂O₃S
• 分子量: 318.397
• InChiKey: NVFZLZINXBEXLY-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  432.7±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

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：
  0.31
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-acetyl-6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 生成 ethyl (4S)-3-acetyl-6-methyl-4-phenyl-2-sulfanylidene-1,4-dihydropyrimidine-5-carboxylate
  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：

  2-(2-乙氧基羰基乙基)硫代-6-甲基-4-苯基-1,4-二氢嘧啶-5-羧酸乙酯 反应 1.0h， 生成 ethyl 3-acetyl-6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Kappe, Christian Oliver; Roschger, Peter, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 55 - 64

  摘要：

  DOI：

文献信息

• A Cs2CO3-mediated simple and selective method for the alkylation and acylation of 3,4-dihydropyrimidin-2(1H)-thiones
  作者：Salil Putatunda、Arijit Chakraborty

  DOI：10.1016/j.crci.2013.12.006

  日期：2014.10

  excellent yields in the presence of Cs2CO3, a mild base. The method evidences a selective S-alkylation when using acyl chlorides as efficient acylating agents at room temperature on the 2-thioxo-dihydropyrimidone moiety. A possible mechanistic interpretation of the different selectivities in case of alkylation and acylation was done with the help of a geometry optimization process.

  摘要 在 Cs2CO3（一种弱碱）存在下，合成了 3,4-二氢嘧啶-2(1H)-硫酮的烷基和酰基衍生物，收率非常好。该方法证明了在室温下使用酰氯作为 2-硫代-二氢嘧啶酮部分上的有效酰化剂时的选择性 S-烷基化。在几何优化过程的帮助下，对烷基化和酰化的不同选择性进行了可能的机械解释。
• 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。
• Substituted pyrimidines useful as calcium channel blockers
  申请人：Merck & Co., Inc.

  公开号：US04675321A1

  公开（公告）日：1987-06-23

  Pharmaceutical compositions of specific substituted pyrimidines and methods of treatment of certain cardiovascular disorders are disclosed. Also disclosed are novel substituted acrylated pyrimidines which are useful as calcium channel blockers.

  本发明揭示了特定取代嘧啶的制药组合物以及治疗某些心血管疾病的方法。还揭示了新型的取代丙烯酸嘧啶，其可用作钙通道阻滞剂。
• KAPPE, CHRISTIAN OLIVER;ROSCHGER, PETER, J. HETEROCYCL. CHEM., 26,(1989) N, C. 55-64
  作者：KAPPE, CHRISTIAN OLIVER、ROSCHGER, PETER

  DOI：——

  日期：——
• US4675321A
  申请人：——

  公开号：US4675321A

  公开（公告）日：1987-06-23