4-cyclohexyl-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester | 112080-31-6

• 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: 4-cyclohexyl-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
• 英文别名: ethyl 4-cyclohexyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；Ethyl 4-cyclohexyl-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；ethyl 4-cyclohexyl-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 112080-31-6
• 化学式: C₁₄H₂₂N₂O₃
• 分子量: 266.34
• InChiKey: OUEAJWSKZFZMMI-UHFFFAOYSA-N

物化性质

• 熔点：
  237.5-238.5 °C
• 沸点：
  373.3±42.0 °C(Predicted)
• 密度：
  1.116±0.06 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：
  0.71
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-cyclohexyl-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 在 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.42h， 以85%的产率得到ethyl 4-cyclohexyl-6-methyl-2-oxo-1H-pyrimidine-5-carboxylate
  参考文献：
  名称：

  4-Bis(triphenylphosphonium)-2-butene peroxodisulfate as an efficient oxidizing agent for one-pot synthesis of ethyl pyrimidin-2(1H)-one-5-carboxylates

  摘要：

  An efficient one-pot synthesis of pyrimidin-2(1H)-ones via three-component condensation of aldehyde, ethyl acetoacetate and urea using 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate [BTPBPDS] as an oxidant is described.

  DOI：

  10.1134/s1070363217040284
• 作为产物：
  描述：

  2-(cyclohexanylmethylene)-3-oxobutanoic acid ethyl ester 在 盐酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-cyclohexyl-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  O'Reilly, Brian C.; Atwal, Karnail S., Heterocycles, 1987, vol. 26, # 5, p. 1185 - 1188

  摘要：

  DOI：

文献信息

• Organocatalytic Application of Ionic Liquids: [bmim][MeSO4] as a Recyclable Organocatalyst in the Multicomponent Reaction for the Preparation of Dihydropyrimidinones and -thiones
  作者：Asit Chakraborti、Sudipta Roy、Pradeep Jadhavar、Kapileswar Seth、Kulin Sharma

  DOI：10.1055/s-0030-1260067

  日期：2011.7

  substitution in the latter. The ionic liquid can be recovered and reused for five consecutive reactions without significant loss of catalytic efficiency. The applicability of the methodology for large-scale reaction highlights its potential for bulk synthesis. ionic liquid - organocatalyst - multicomponent reaction - dihydropyrimidinone - dihydropyrimidinethione

  已经研究了基于1-丁基-3-甲基咪唑鎓的室温离子液体的有机催化潜力，该反应通过单锅多组分反应（包括醛，β-酮酸酯或β-二酮）合成二氢嘧啶酮和-硫酮，尿素或硫脲在短时间内的收率很高。研究了影响离子液体作为催化剂效率的因素，例如阴离子和咪唑鎓阳离子，特别是后者中C2取代的影响。可以回收离子液体并将其重新用于五个连续的反应，而不会显着降低催化效率。该方法用于大规模反应的适用性突出了其本体合成的潜力。 离子液体-有机催化剂-多组分反应-二氢嘧啶酮-二氢嘧啶硫酮
• Samarium Triflate–Catalyzed Biginelli Condensation: An Improved Method for the Synthesis of 3,4-Dihydropyrimidin-2(<i>1H</i>)-ones
  作者：A. Venkat Narsaiah、A. Ramesh Reddy、J. S. Yadav

  DOI：10.1080/00397911.2010.515355

  日期：2011.9.15

  Abstract A simple and efficient method for multicomponant synthesis of 3,4-dihydropyrimidinones has been reported. All the reactions were carried out using samarium triflate as catalyst (10 mol%) at acetonitrile reflux. This procedure is applicable to a variety of substrates such as aliphatic, aromatic, and heterocyclic aldehydes.

  摘要 报道了一种简单有效的多组分合成 3,4-二氢嘧啶酮的方法。所有反应均使用三氟甲磺酸钐作为催化剂（10 mol%）在乙腈回流下进行。此程序适用于各种底物，如脂肪族、芳香族和杂环醛。
• Ionic liquid-assisted synthesis of dihydropyrimidin(thi)one Biginelli adducts and investigation of their mechanism of urease inhibition
  作者：Taniris Cafiero Braga、Thamara Ferreira Silva、Thamilla Maria Silva Maciel、Edjan Carlos Dantas da Silva、Edeildo Ferreira da Silva-Júnior、Luzia Valentina Modolo、Isis Martins Figueiredo、Josué Carinhanha Caldas Santos、Thiago Mendonça de Aquino、Ângelo de Fátima

  DOI：10.1039/c9nj03556g

  日期：——

  Twenty-six Biginelli adducts were synthesized through an ionic liquid-assisted synthesis with up to 92% yield. Sixteen of these Biginelli adducts were then assayed to determine their antiureolytic activity against purified urease from jack beans. The substances BA7-S, BA9-S and BA11-S were shown to be as efficient inhibitors as hydroxyurea, a positive control used in in vitro screening assay against

  通过离子液体辅助合成法合成了26种Biginelli加合物，收率高达92％。然后分析这些Biginelli加合物中的16种，以确定它们对来自千斤顶豆的纯化脲酶的抗脲水解活性。物质BA7-S，BA9-S和BA11-S被证明是与羟基脲有效的抑制剂，羟基脲是用于体外抗脲酶筛选试验的阳性对照。荧光研究表明，BA7-S，BA9-S，BA11-S和BA5-S分别具有5.95、6.72、4.55和4.28 M -1的高结合常数，而BAS12-S无取代基的log K b = 2.16 M -1的值低 。另外，在最热力学上有利的BA5-S和BA7-S脲酶复合物中，相应的Biginelli加合物能够通过非离子相互作用（例如疏水相互作用或氢和范德华相互作用）与脲酶的活性位点相互作用， 分别。计算机分析研究还支持BA与活性位点相互作用，从而证实了荧光和动力学分析研究，这清楚表明BA5-S和BA7-S是竞争性抑制剂（K
• Cu(OTf)2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones
  作者：A.S. Paraskar、G.K. Dewkar、A. Sudalai

  DOI：10.1016/s0040-4039(03)00619-1

  日期：2003.4

  Copper(II) triflate catalyzes efficiently the three-component condensation reaction of an aldehyde, β-ketoester and urea in acetonitrile to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones in high yields. The catalyst exhibited remarkable reusable activity.

  三氟甲磺酸铜（II）有效催化醛，β-酮酸酯和尿素在乙腈中的三组分缩合反应，从而以高收率提供相应的3,4-二氢嘧啶-2（1 H）-酮。该催化剂表现出显着的可重复使用的活性。
• Facile Biginelli-Type Reactions Catalysed by Super Acidic Ionic Liquid under Solvent-Free Conditions
  作者：Liang Wang、Min Zhou、Qun Chen、Ming-Yang He

  DOI：10.3184/174751912x13518654161237

  日期：2012.12

  [MeC(OH)2]+ClO4- as a super acidic ionic liquid is an extremely active catalyst for Biginelli-type reactions. The present method is especially effective for the inactive aliphatic aldehydes. The solvent-free conditions, high catalytic activity, wide substrates tolerance and convenient product isolation make the protocol more advantageous.

  [MeC(OH)2]+ClO4- 作为一种超酸性离子液体，是一种非常活跃的 Biginelli 型反应催化剂。本方法对惰性脂肪醛特别有效。无溶剂条件、高催化活性、广泛的底物耐受性和方便的产品分离使该协议更具优势。