1,3-dimethyl-5-piperonylbarbituric acid | 300838-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1,3-dimethyl-5-piperonylbarbituric acid
• 英文别名: 5-(1,3-benzodioxol-5-ylmethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione；5-(1,3-benzodioxol-5-ylmethyl)-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 300838-06-6
• 化学式: C₁₄H₁₄N₂O₅
• mdl: MFCD00552573
• 分子量: 290.276
• InChiKey: VZKWQHSZARRBJR-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  420.9±53.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 cytisine 、 1,3-dimethyl-5-piperonylbarbituric acid 以 水 为溶剂， 反应 1.0h， 以81%的产率得到5-(1,3-benzodioxol-5-ylmethyl)-1,3-dimethyl-5-[[(1R,9S)-6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-11-yl]methyl]-1,3-diazinane-2,4,6-trione
  参考文献：
  名称：

  Chemical modification of plant alkaloids. I. Aminomethylation of barbituric acid derivatives by cytisine

  摘要：

  Reaction of cytisine with 1-mono- and 1,3-disubstituted 5-arylmethylbarbituric acids in the presence of formaldehyde results in aminomethylation of C-5 to form the corresponding 5-cytisylmethylbarbituric acids. The structures of the products are found using PMR spectroscopy mid mass spectrometry. 1-Phenyl-5-(2,4-dimethoxybenzyl)-5-cytisylmethylbarbituric acid is obtained as a mixture of two steroisomers in an approximately 2:1 ratio.

  DOI：

  10.1007/bf02236429
• 作为产物：
  描述：

  5-(benzo[d] [1,3]dioxol-5-ylmethylene)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione 在 sodium tetrahydroborate 作用下， 以 水 、 异丙醇 为溶剂， 以85%的产率得到1,3-dimethyl-5-piperonylbarbituric acid
  参考文献：
  名称：

  Chemical modification of plant alkaloids. I. Aminomethylation of barbituric acid derivatives by cytisine

  摘要：

  Reaction of cytisine with 1-mono- and 1,3-disubstituted 5-arylmethylbarbituric acids in the presence of formaldehyde results in aminomethylation of C-5 to form the corresponding 5-cytisylmethylbarbituric acids. The structures of the products are found using PMR spectroscopy mid mass spectrometry. 1-Phenyl-5-(2,4-dimethoxybenzyl)-5-cytisylmethylbarbituric acid is obtained as a mixture of two steroisomers in an approximately 2:1 ratio.

  DOI：

  10.1007/bf02236429

文献信息

• Sequential one-pot bimetallic Ir(<scp>iii</scp>)/Pd(<scp>0</scp>) catalysed mono-/bis-alkylation and spirocyclisation processes of 1,3-dimethylbarbituric acid and allenes
  作者：Christian Löfberg、Ronald Grigg、Ann Keep、Andrew Derrick、Visuvanathar Sridharan、Colin Kilner

  DOI：10.1039/b614098j

  日期：——

  Microwave assisted indirect functionalization of alcohols with 1,3-dimethylbarbituric acid followed by spirocyclisation employing a sequential one-pot Ir(III)/Pd(0) catalysed process, involving the formation of three new C–C bonds, one spirocyclic ring and one di- or tri-substituted exocyclic alkene, is described.

  微波辅助下，通过一步连续的Ir(III)/Pd(0)催化反应，利用1,3-二甲基巴比妥酸对醇进行间接官能团化，随后进行螺环化反应，涉及形成三个新的C–C键、一个螺环结构以及一个二取代或三取代的环外烯烃，这一过程得以描述。
• Ruthenium-catalyzed selective synthesis of monoalkylated barbituric acids through “borrowing hydrogen” methodology
  作者：Anggi Eka Putra、Yohei Oe、Tetsuo Ohta

  DOI：10.1016/j.tetlet.2017.01.070

  日期：2017.3

  An environmentally benign alkylation of barbituric acids via “borrowing hydrogen” process with ruthenium catalysis has been established. The corresponding 5-(alkyl)barubituric acids were obtained in good to excellent yields with low catalyst loading. Various substrates including aliphatic alcohols were tolerated in the present catalytic system. A novel method for construction of barbituric acid-fused

  已经建立了通过“借入氢”过程和钌催化对巴比妥酸进行无害环境的烷基化反应。以良好的至优异的产率和较低的催化剂负载量获得了相应的5-（烷基）Barubituric酸。在本催化体系中，包括脂肪族醇在内的各种底物是可以容忍的。还证明了一种新的构建巴比妥酸稠合的苯并吡喃衍生物的方法。
• Iridium supported on porous polypyridine-oxadiazole as high-activity and recyclable catalyst for the borrowing hydrogen reaction
  作者：Jiahao Li、Anruo Mao、Wei Yao、Haiyan Zhu、Dawei Wang

  DOI：10.1039/d2gc00190j

  日期：——

  HRTEM, SEM, and XPS, and revealed high catalytic activity for the reaction of dimethyl-6-aminouracil with benzyl alcohols, 1,3-dimethylbarbituric acid with benzyl alcohols and 2-aminobenzylamine and benzyl alcohols through dehydrogenation and the borrowing hydrogen strategy with alcohol or water as the solvent. In addition, this PPO-Ir catalyst could be recycled and reused without a manifest loss of

  多相催化剂的均质化是一个有价值和有趣的研究课题。以吡啶-恶二唑和1-碘-4-乙烯基苯为原料，设计并合成了多孔聚吡啶-恶二唑（PPO）作为载体和配体。铱通过配位键固定在这种聚合物（配体）的骨架上。这种多孔聚吡啶-恶二唑铱催化剂 (PPO-Ir) 通过 XRD、BET、EDS、HRTEM、SEM 和 XPS 清楚地表征，并显示出对二甲基-6-氨基尿嘧啶与苯甲醇 1,3 反应的高催化活性-二甲基巴比妥酸与苄醇和2-氨基苄胺与苄醇通过脱氢和借氢策略以醇或水为溶剂。此外，这种 PPO-Ir 催化剂可以回收再利用，至少 5 次没有明显的催化活性损失，并显示出潜在的应用价值。进一步进行机制探索以阐明该PPO-Ir和这些转变。
• Chemical modification of plant alkaloids. I. Aminomethylation of barbituric acid derivatives by cytisine
  作者：K. A. Krasnov、V. G. Kartsev、A. S. Gorovoi

  DOI：10.1007/bf02236429

  日期：2000.3

  Reaction of cytisine with 1-mono- and 1,3-disubstituted 5-arylmethylbarbituric acids in the presence of formaldehyde results in aminomethylation of C-5 to form the corresponding 5-cytisylmethylbarbituric acids. The structures of the products are found using PMR spectroscopy mid mass spectrometry. 1-Phenyl-5-(2,4-dimethoxybenzyl)-5-cytisylmethylbarbituric acid is obtained as a mixture of two steroisomers in an approximately 2:1 ratio.