ethyl 4,6-dimethyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 134074-26-3

• 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: ethyl 4,6-dimethyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4,6-dimethyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 134074-26-3
• 化学式: C₉H₁₄N₂O₂S
• mdl: MFCD01208217
• 分子量: 214.288
• InChiKey: XFOVQDPQEDSLQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.555
• 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：

  ethyl 4,6-dimethyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 N,N-二异丙基乙胺 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 氯苯 为溶剂， 反应 43.5h， 生成 ethyl 6,8-dimethyl-4-oxo-3,4,6,9-tetrahydropyrimido[2,1-c][1,2,4,6]thiatriazine-7-carboxylate 2,2-dioxide
  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：

  ethyl 4-hydroxy-4,6-dimethyl-2-thioxohexahydropyrimidine-5-carboxylate 在 对甲苯磺酸 作用下， 以0.671 g的产率得到ethyl 4,6-dimethyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A General Approach to 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) via α-(thio)ureidoalkylation of 1,3-diketones or β-oxoesters

  摘要：

  我们开发出了一种新的通用方法，可用于制备迄今为止难以获得的大量 4-未取代和 4-烷基取代的 5-酰基-1,2,3,4-四氢嘧啶-2-亚硫酰（一）。该方法基于各种 1,3-二酮或β-氧代酯的烯醇化物与容易获得的 N-[烷基（甲苯基）甲基]硫脲、N-（叠氮甲基）硫脲和 N-[烷基（甲苯基）甲基]脲反应，然后在 TsOH 催化下对中间体 4-羟基六氢嘧啶-2-硫酮（一）进行脱水，而不分离或分离后者。

  DOI：

  10.1007/s10593-023-03146-6

文献信息

• Oxidative transformation of thiols to disulfides promoted by activated carbon–air system
  作者：Masahiko Hayashi、Ken-ichi Okunaga、Shunsuke Nishida、Kenjiro Kawamura、Kazuo Eda

  DOI：10.1016/j.tetlet.2010.10.070

  日期：2010.12

  Efficient oxidative transformation of thiols to disulfides took place in the presence of activated carbon under an oxygen (or air) atmosphere. The present oxidation method is available not only for a variety of thiols such as simple aromatic and aliphatic thiols but also for 3,4-dihydropyrimidin-2(1H)-thiones and N-Boc-l-cysteine.

  在氧气（或空气）气氛下，在存在活性炭的情况下，硫醇进行了有效的氧化转化为二硫化物。本氧化方法不仅可用于多种硫醇，例如简单的芳族和脂族硫醇，而且可用于3,4-二氢嘧啶-2（1 H）-硫酮和N- Boc- 1-半胱氨酸。
• Oxidative Dehydrosulfurative Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Alkynes for Access to 2-Alkynylpyrimidines
  作者：Ngoc Son Le Pham、Hyunik Shin、Jun Yong Kang、Jeong-Hun Sohn

  DOI：10.1021/acs.joc.0c00091

  日期：2020.4.3

  (DHPMs) via dehydrosulfurative Sonogashira cross-coupling with concomitant oxidative dehydrogenation using a Pd/Cu catalytic system. Together with the ready availability of DHPMs possessing various substituents at the C4–C6 positions, this transformation offers rapid and general access to diverse 2-alkynylpyrimidine derivatives.

  描述了一种通过Pd / Cu催化体系通过脱硫Sonogashira交叉偶联与伴随的氧化脱氢从3,4-二氢嘧啶-1 H -2-硫酮（DHPM）一步合成2-炔基嘧啶的反应方法。连同在C4–C6位置具有各种取代基的DHPM的现成可用性，这种转变为获得各种2-炔基嘧啶衍生物提供了快速而通用的途径。
• An expedient protocol of the Biginelli dihydropyrimidine synthesis using carbonyl equivalents
  作者：Kamaljit Singh、Jasbir Singh、Prasant K. Deb、Harjit Singh

  DOI：10.1016/s0040-4020(99)00760-7

  日期：1999.10

  A one - pot condensation of perhydro-1,3 heterocycles - aldehyde equivalents with ethyl acetoacetate and ureas provides a convenient synthesis of the title compounds with a variety of substituents at C-4. Yields are equivalent or significantly higher than the conventional methods.

  全氢-1,3杂环-醛当量与乙酰乙酸乙酯和脲的一锅缩合反应可方便地合成标题化合物，其在C-4处具有多个取代基。产率与常规方法相当或相当高。
• Synthesis and bioactivity of several new hetaryl sulfonamides
  作者：Parham Taslimi、Afsun Sujayev、Sevgi Mamedova、Pınar Kalın、İlhami Gulçin、Nastaran Sadeghian、Sukru Beydemir、O. Irfan Kufrevioglu、Saleh H. Alwasel、Vagif Farzaliyev、Sabir Mamedov

  DOI：10.1080/14756366.2016.1238367

  日期：2017.1.1

  was detected in high concentrations in the brain and red blood cells. BChE is another enzymes that is abundant available in the liver and released into the blood in a soluble form. Newly synthesized hetaryl sulfonamides exhibited impressive inhibition profiles with Ki values in the range of 1.42-6.58 nM against hCA I, 1.72-7.41 nM against hCA II, 0.20-1.14 nM against AChE and 1.55-5.92 nM against BChE

  由不同的四氢嘧啶硫酮和芳基磺酰氯合成1-（4-甲基磺酰基）-2-硫酮-4-芳基-5-Z-6-甲基和氧烷基-咪唑。测试了这些化合物的金属螯合作用，并确定了在两个生理相关化合物与碳酸酐酶（CA）同工酶I和II（hCA I和II），丁酰胆碱酯酶（BChE）和乙酰胆碱酯酶（AChE）之间产生抑制作用的短语。在脑和红细胞中检测到高浓度的AChE。BChE是另一种在肝脏中可用并以可溶形式释放到血液中的酶。新合成的杂芳基磺酰胺类药物显示出令人印象深刻的抑制特性，Ki值对hCA I的范围为1.42-6.58 nM，对hCA II为1.72-7.41 nM，对AChE为0.20-1.14 nM，对BChE为1.55-5.92 nM。此外，乙酰唑胺对hCA I的Ki值为43.69±6.44 nM，对hCA II的Ki值为31.67±8.39 nM。此外，他克林对AChE和BChE的Ki值分别为25.75±3.39
• Lipase-Initiated Tandem Biginelli Reactions <i>via in situ</i> -Formed Acetaldehydes in One Pot: Discovery of Single-Ring Deep Blue Luminogens
  作者：Wei Zhang、Na Wang、Zeng-Jie Yang、Yan-Rong Li、Yuan Yu、Xue-Mei Pu、Xiao-Qi Yu

  DOI：10.1002/adsc.201700599

  日期：2017.10.4

  A facile approach for the synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones was developed by a tandem multi‐component reaction (MCR) in one pot. This approach involves two steps, lipase‐catalyzed in situ generation of acetaldehyde and the Biginelli reaction in turn. Several control experiments were performed using acetaldehydes directly to explore the possible mechanism of this procedure. Moreover, owing

  通过在一个锅中进行串联多组分反应（MCR），开发了一种简便的合成3,4-二氢嘧啶-2（1 H）-1的方法。该方法涉及两个步骤：脂肪酶催化的乙醛原位生成和Biginelli反应。直接使用乙醛进行了几次对照实验，以探讨该程序的可能机理。而且，由于MCR具有独特的模块化和高效功能，它可以组装结构多样的产品库（在本文的优化条件下，收率高达98％），并提供了一种出色的合成工具，可用于发现最小的深度-固态的蓝色发光剂，即单环。