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.
• Nickel Nanoparticles: An Ecofriendly and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones via Biginelli Reaction
  作者：Suryakant B. Sapkal、Kiran F. Shelke、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.5012/bkcs.2010.31.02.351

  日期：2010.2.20

  Nickel nanoparticles (Ni NPs) appeared to exhibit the catalytic activity in one-pot cyclocondensation reaction for the preparation of 3,4-dihydropyrimidine-2(1H)-ones via Biginelli reaction from aromatic/heteroaromatic/aliphatic aldehydes, urea/thiourea and ethyl acetoacetate under microwave irradiation has been described. The UV absorbance spectra showed metallic Ni characteristics and appreciate with the particle size determined by Transmission electron microscopy (TEM). After reaction course the Ni NPs can be re-covered and reused without any apparent loss of activity.

  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。
• Synthesis of Some New 3-Oxo-2-[(<i>Z</i>)-1-phenylmethylidene]-5<i>H</i>-[1,3]thiazolo[3,2-<i>a</i>]-and <i>N</i>-Acetylated Pyrimidines
  作者：A. Mobinikhaledi、N. Foroughifar、J. Alipour Safari、T. Mosleh

  DOI：10.1080/10426500701441457

  日期：2008.9.5

  3-Oxo-2-[(Z)-1-phenylmethylidene]-5H-[1,3]thiazolo[3,2-a] pyrimidine derivatives 2a–f were synthesized by the reaction of an appropriate 3,4-dihydro-2(H)-pyrimidone 1 , chloroacetic acid, sodium acetate and benzaldehyde. Reaction of 1 with acetic anhydride under heating afforded only 3-N-acetylated 3,4-dihydro-2(H)-pyrimidines 3a–f . The yields of the products after recrystallization from ethanol were

  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。