4-isopropyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-thione | 571903-57-6

• 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-isopropyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-thione
• 英文别名: 4-isopropyl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester；ethyl 4-methyl-6-(methylethyl)-2-thioxo-1,3,6-trihydropyrimidine-5-carboxylate；ethyl 6-methyl-4-propan-2-yl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 571903-57-6
• 化学式: C₁₁H₁₈N₂O₂S
• 分子量: 242.342
• InChiKey: DNSDUOPNEGQGBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  4-isopropyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-thione 在 三氟甲烷磺酸甲酯 、 ammonium acetate 、 氨 作用下， 以 氯苯 为溶剂， 反应 20.5h， 以33%的产率得到ethyl 2-amino-4-(methylethyl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Condensation reactions of guanidines with bis-electrophiles: formation of highly nitrogenous heterocycles

  摘要：

  2-Amino-1,4-dihydropyrimidines were reacted with bis-electrophiles to produce novel fused bipyrimidine, pyrimidoaminotriazine, and pyrimidosulfonamide scaffolds. In addition, a quinazoline library was constructed using a guanidine Atwal-Biginelli reaction with 1-(quinazolin-2-yl)guanidines. The product heterocycles have novel constitutions with high nitrogen atom counts and represent valuable additions to screening libraries for the discovery of new modulators of biological targets. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.127
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 硫脲 、 异丁醛 在 苄基三乙基氯化铵 作用下， 反应 1.5h， 以86%的产率得到4-isopropyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-thione
  参考文献：
  名称：

  在无溶剂条件下合成一些2-氧代和2-硫代取代的嘧啶

  摘要：

  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。

  DOI：

  10.1002/jhet.5570440329

文献信息

• Mild and efficient oxidative aromatization of 4-substituted-1,4-dihydropyrimidines using (diacetoxyiodo)benzene
  作者：Nandkishor N. Karade、Sumit V. Gampawar、Nilesh P. Tale、Sanjay B. Kedar

  DOI：10.1002/jhet.389

  日期：——

  4‐Alkyl or aryl‐1,4‐dihydropyrimidines were readily oxidized by (diacetoxyiodo)benzene under mild reaction conditions to the corresponding pyrimidine derivatives in good to excellent yields. J. Heterocyclic Chem., (2010).

  4-烷基或芳基-1,4-二氢嘧啶很容易在温和的反应条件下被（二乙酰氧基碘）苯氧化为相应的嘧啶衍生物，收率很好。J.杂环化​​学。（2010）。
• Synthesis of 2-substituted pyrimidines and benzoxazoles via a visible-light-driven organocatalytic aerobic oxidation: enhancement of the reaction rate and selectivity by a base
  作者：Lin Wang、Zhi-Gang Ma、Xiao-Jing Wei、Qing-Yuan Meng、Deng-Tao Yang、Shao-Fu Du、Zi-Fei Chen、Li-Zhu Wu、Qiang Liu

  DOI：10.1039/c4gc00337c

  日期：——

  An efficient visible-light-driven photocatalytic oxidation of various 2-substituted dihydropyrimidines and phenolic imines has been achieved using an organic photocatalyst eosin Y bis(tetrabutyl ammonium salt) (TBA-eosin Y) and inexpensive oxidant molecular oxygen. With the aid of a base, significantly enhanced photoinduced electron transfer from substrates dihydropyrimidines or phenolic imines to the excited state of TBA-eosin Y has enabled the aerobic oxidation to yield 2-(methylthio)pyrimidines or 2-arylbenzoxazoles selectively.

  利用有机光催化剂藻红Y双(四丁基铵盐)(TBA-藻红Y)和廉价氧化剂分子氧，已经实现了各种2-取代二氢嘧啶和酚亚胺的高效可见光驱动光催化氧化反应。在碱的辅助下，从底物二氢嘧啶或酚亚胺到TBA-藻红Y激发态的显著增强的光诱导电子转移，使得空气氧化能够选择性地生成2-(甲硫基)嘧啶或2-芳基苯并噁唑。
• An Efficient One-Pot Synthesis of Dihydropyrimidinones by a Samarium Diiodide Catalyzed Biginelli Reaction Under Solvent-Free Conditions
  作者：Xiaoyan Han、Fan Xu、Yiqin Luo、Qi Shen

  DOI：10.1002/ejoc.200400753

  日期：2005.4

  The Biginelli reaction, a one-pot condensation of aldehydes, urea or thiourea, and β-dicarbonyl compounds, is efficiently catalyzed by samarium diiodide. The biologically active dihydropyrimidinones are easily synthesized in moderate to excellent yields under solvent-free conditions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  Biginelli 反应是醛、尿素或硫脲和 β-二羰基化合物的一锅缩合反应，由二碘化钐有效催化。生物活性二氢嘧啶酮在无溶剂条件下很容易以中等至极好的收率合成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• 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。
• Convenient One‐Pot Heterogeneous Catalytic Method for the Preparation of 3,4‐Dihydropyrimidin‐2(<i>1H</i>)‐ones
  作者：Adrienn Hegedüs、Zoltán Hell、Ilona Vígh

  DOI：10.1080/00397910500330858

  日期：2006.2

  aromatic and aliphatic aldehydes, ethyl acetoacetate, and urea or thiourea using a small‐pore‐size zeolite as catalyst is described. Compared with the classical Biginelli reaction conditions, this method has the advantage of high yield, shorter reaction time, and recyclable and reusable catalyst.

  摘要描述了使用小孔径沸石作为催化剂，由芳香族和脂肪族醛、乙酰乙酸乙酯和尿素或硫脲合成二氢嘧啶酮的一种新的、简单的、环保的方法。与经典的Biginelli反应条件相比，该方法具有收率高、反应时间短、催化剂可回收再利用等优点。