4-butyl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester

• 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-butyl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester
• 英文别名: ethyl-4-butyl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；4-n-butyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-thione；ethyl 4-butyl-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₂H₂₀N₂O₂S
• 分子量: 256.369
• InChiKey: XZZDZAOMRSFSTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 氯乙酸 、 4-butyl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester 在 sodium acetate 作用下， 以 1,4-二氧六环 为溶剂， 以56%的产率得到ethyl 5-butyl-7-methyl-3-oxo-2-[(Z)-1-phenylmethylidene]-5H-[1,3]thiazolo[3,2-a]pyrimidine-6(3H)-carboxylate
  参考文献：
  名称：

  一些新型3-Oxo-2-[(Z)-1-苯基亚甲基]-5H-[1,3]噻唑并[3,2-a]-和N-乙酰化嘧啶的合成

  摘要：

  3-Oxo-2-[(Z)-1-苯基亚甲基]-5H-[1,3]噻唑并[3,2-a]嘧啶衍生物2a-f是通过适当的3,4-二氢- 2(H)-嘧啶酮1、氯乙酸、乙酸钠和苯甲醛。1 与乙酸酐在加热下反应仅得到 3-N-乙酰化 3,4-二氢-2(H)-嘧啶 3a-f。从乙醇中重结晶后产物的产率约为 60-92%。IR、 1 H NMR 光谱和元素分析用于鉴定这些化合物。

  DOI：

  10.1080/10426500701441457
• 作为产物：
  描述：

  正戊醛 、 乙酰乙酸乙酯 、 硫脲 在 nickel nanoparticles (Ni NPs) 作用下， 反应 0.12h， 以80%的产率得到4-butyl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Nickel Nanoparticles: An Ecofriendly and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones via Biginelli Reaction

  摘要：

  镍纳米颗粒（Ni NPs）在微波辐射下，能够在一锅法环缩合反应中表现出催化活性，用于从芳香族/杂芳香族/脂肪族醛、尿素/硫脲和乙基乙酰乙酸酯制备3,4-二氢嘧啶-2(1H)-酮，通过比吉内利反应已被描述。紫外吸收光谱显示出金属镍的特征，并且粒径通过透射电子显微镜（TEM）确定。反应结束后，Ni NPs可以重新回收并重复使用，且没有明显的活性损失。

  DOI：

  10.5012/bkcs.2010.31.02.351

文献信息

• Synthesis of some 2-oxo and 2-thioxo substituted pyrimidines using solvent-free conditions
  作者：Akbar Mobinikhaledi、Naser Forughifar、Jil A. Alipour Safari、EhsaN. Amini

  DOI：10.1002/jhet.5570440329

  日期：2007.5

  three components cyclocondensation reaction of β-ketoester, aldehyde and urea/thiourea using benzyltriethylammonium chloride as a catalyst under solvent-free conditions. The yields of products following recrystallization from ethanol were of the order of 65-87%. IR and 1HNMR spectroscopy and elemental analysis were used for identification of these compounds.

  在无溶剂的条件下，以苄基三乙基氯化铵为催化剂，通过β-酮酸酯，醛和脲/硫脲的三锅单组分三环缩合反应，合成了一系列氧代和硫代嘧啶4（am）。用乙醇重结晶后的产物产率为65-87％。红外和1 HNMR光谱和元素分析用于鉴定这些化合物。
• Lanthanide Triflate Catalyzed One-Pot Synthesis of Dihydropyrimidin-2(1<i>H</i>)-thiones by a Three-Component of 1,3-Dicarbonyl Compounds, Aldehydes, and Thiourea Using a Solvent-Free Biginelli Condensation
  作者：Limin Wang、Changtao Qian、He Tian、Yun Ma

  DOI：10.1081/scc-120018755

  日期：2003.1.5

  Novel one-pot Biginelli-type reaction has been developed. Aromatic and aliphatic aldehydes with beta-dicarbonyl compounds and thiourea in the presence of catalytic amount 5 mol% of Yb(OTf)3 at 100degrees C for 60-90 min under solvent-free conditions proceeded smoothly to afford corresponding dihydropyrimidin-thiones. The yields of the classical Biginelli reaction can be increased from 20-50% to 81-91 % while the reaction time was shortened from 18-48 h to 60-90 min. In addition the catalyst can be easily recovered and reused.
• Al₂O₃/MeSO₃H: A Novel and Recyclable Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidinones or Their Sulfur Derivatives in Biginelli Condensation
  作者：Hashem Sharghi、Mahboubeh Jokar

  DOI：10.1080/00397910802444258

  日期：2009.2.25

  Al2O3/CH3SO3H (AMA) is an efficient catalyst for the three-component condensation reaction of aldehyde, 1,3-dicarbonyl compound, and urea or thiourea to afford the corresponding 3,4-dihydropyrimidin-2-(1H)-ones in high isolated yield via this procedure, which works very effectively regardless of the electronic nature of the substituent on the ring, although electron-donating groups precipitate the rate of reaction. The catalyst is recyclable and stable at room temperature, and the reaction protocol is simple, is cost-effective, and gives good isolated yield with high purity.