methyl 6-methyl-4-(naphthalen-2'-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6-methyl-4-(naphthalen-2'-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: methyl 6-methyl-4-(naphthalen-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；Methyl 6-methyl-4-(2-naphthyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；methyl 6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: PXLQWELVNYBRRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸甲酯 、 2-萘甲醛 、 尿素 在 C₂₀H₁₈N₂O₄Zr⁽²⁺⁾*2C₈F₁₇O₃S^(1-) 作用下， 以 neat (no solvent) 为溶剂， 反应 0.67h， 以85%的产率得到methyl 6-methyl-4-(naphthalen-2'-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  空气稳定的锆（IV）-三氯苯酚全氟辛烷磺酸盐是在无溶剂条件下合成3,4-二氢嘧啶-2-（1H）-酮/硫酮的高效且可重复使用的催化剂

  摘要：

  通过使Zr（salphen）Cl 2与C 8 F 17 SO 3 Ag反应成功合成了一种空气稳定的锆（IV）-salophen全氟辛烷磺酸盐（1）。配合物1通过不同的技术（NMR，IR，HRMS，TG-DSC，电导率和酸度测量）进行了表征和研究，被发现具有空气稳定性，耐水性，热稳定性和强路易斯酸性。络合物1在无溶剂条件下通过醛，1,3-二羰基化合物和脲/硫脲的Biginelli反应合成3,4-二氢嘧啶-2-（1H）-酮/硫酮具有很高的催化效率。此外，复数1可以重复使用5次，而催化效率的变化却很小。与以前报道的方法相比，该方案的重要特征是无溶剂条件，反应时间短，底物相容性广，效率高和可重复使用性好。

  DOI：

  10.1002/aoc.5454

文献信息

• Methods and compositions for treating pain
  申请人：Moran M. Magdalene

  公开号：US20070219222A1

  公开（公告）日：2007-09-20

  The present application relates to compounds and methods for treating pain, incontinence and other conditions.

  本申请涉及化合物和治疗疼痛、失禁和其他疾病的方法。
• Dihydropyrimidones: As novel class of β-glucuronidase inhibitors
  作者：Farman Ali、Khalid Mohammed Khan、Uzma Salar、Sarosh Iqbal、Muhammad Taha、Nor Hadiani Ismail、Shahnaz Perveen、Abdul Wadood、Mehreen Ghufran、Basharat Ali

  DOI：10.1016/j.bmc.2016.06.002

  日期：2016.8

  Dihydropyrimidones 1–37 were synthesized via a ‘one-pot’ three component reaction according to well-known Biginelli reaction by utilizing Cu(NO3)2·3H2O as catalyst, and screened for their in vitro β-glucuronidase inhibitory activity. It is worth mentioning that amongst the active molecules, compounds 8 (IC50 = 28.16 ± .056 μM), 9 (IC50 = 18.16 ± 0.41 μM), 10 (IC50 = 22.14 ± 0.43 μM), 13 (IC50 = 34.16 ± 0

  Dihydropyrimidones 1 - 37分别经由“一锅”根据通过利用铜公知的Biginelli反应三个组分反应而合成（NO 3）2 ·3H 2 O作为催化剂，并筛选它们的体外β葡萄糖醛酸酶抑制活性。值得一提的是，在活性分子中，化合物8（IC 50  = 28.16±.056μM），9（IC 50  = 18.16± 0.41μM ），10（IC 50  = 22.14±0.43μM），13（IC 50  = 34.16±0.65μM），14（IC 50  = 17.60±0.35μM），15（IC 50  = 15.19±0.30μM），16（IC 50  = 27.16±0.48μM），17（IC 50  = 48.16±1.06μM），22（IC 50  = 40.16±0.85μM），23（IC 50  = 44.16） ±  0.86μM ），24（IC 50 = 47.16±0
• METHODS AND COMPOSITIONS FOR TREATING PAIN
  申请人：Moran Magdalene M.

  公开号：US20140221401A1

  公开（公告）日：2014-08-07

  The present application relates to compounds and methods for treating pain, incontinence and other conditions.

  本申请涉及用于治疗疼痛、失禁和其他疾病的化合物和方法。
• Zn2+/MCM-41 catalyzed Biginelli reaction of heteroaryl aldehydes and evaluation of the antimicrobial activity and cytotoxicity of the pyrimidone products
  作者：Zarrin Ghasemi、Farzaneh Farshbaf Orafa、Mahtab Pirouzmand、Gholamreza Zarrini、Behnaz Nikzad Kojanag、Roya Salehi

  DOI：10.1016/j.tetlet.2015.09.143

  日期：2015.11

  The three component Biginelli condensation of various aryl aldehydes, 1,3-dicarbonyls and urea was investigated in the presence of free or MCM-41 supported ZnNO3. The pyrimidone products, which were obtained under solvent-free conditions, were evaluated for antibacterial and antifungal activities as well as their cytotoxicities. (C) 2015 Elsevier Ltd. All rights reserved.
• Recyclable Triphenylbismuth(V) Bisperfluorooctanesulfonate Catalyzed Synthesis of Dihydropyrimidinones
  作者：Ablimit Abdukader、Rong Wang、Marhaba Mamat

  DOI：10.3987/com-19-14196

  日期：——

  Triphenylbismuth(V) bisperfluorooctanesulfonate Ph3Bi(OSO2C8F17)(2) was successfully synthesized by treatment of Ph3BiCl2 with C8F17SO2OAg, and was found to have the nature of air-stability, water tolerance, high thermal stability and strong Lewis acidity. This complex showed high catalytic efficiency for the synthesis of dihydropyrimidinones (DHPMs) via three-component reaction of aromatic aldehydes, 1,3-dicarbonyl compound and urea under mild conditions. Furthermore, it can be reused without loss of activity in a test of five cycles. Hence, here we provide a convenient and efficient method for preparation of dihydropyrimidinones.