1,1′,3,3′-tetramethyl-5-(4-nitrophenyl)-1,5-dihydro-2H,2′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′(1′H,3H,3′H)-pentaone | 1260431-69-3

• 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: 1,1′,3,3′-tetramethyl-5-(4-nitrophenyl)-1,5-dihydro-2H,2′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′(1′H,3H,3′H)-pentaone
• 英文别名: 5-(4-nitrophenyl)-1,1',3,3'-tetramethyl-1,5-dihydro-2H,2'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'(1'H,3H,3'H)-pentaone；1,1',3,3'-tetramethyl-5'-(4-nitrophenyl)spiro[1,3-diazinane-5,6'-5H-furo[2,3-d]pyrimidine]-2,2',4,4',6-pentone
• CAS: 1260431-69-3
• 化学式: C₁₉H₁₇N₅O₈
• 分子量: 443.373
• InChiKey: XOANWYZKZHCTBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5,5'-(4-nitrobenzylidene)di(1,3-dimethylbarbituric acid) 在 urotropine-bromine complex 作用下， 以 水 为溶剂， 反应 4.0h， 生成 1,1′,3,3′-tetramethyl-5-(4-nitrophenyl)-1,5-dihydro-2H,2′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′(1′H,3H,3′H)-pentaone
  参考文献：
  名称：

  乌托品-溴通过多米诺骨牌Knoevenagel缩合/ Michael加成/α-溴化/ Williamson环醚化序列促进功能化的氧杂三环呋喃嘧啶的合成

  摘要：

  通过芳香醛和（硫代）的一锅式伪三组分多米诺偶联，已开发出一种有效，安全且简便的途径来官能化螺[furo [2,3- d ]嘧啶-6,5'-嘧啶]衍生物室温下在水中存在乌托品-溴（UB）配合物时的巴比妥酸。该反应顺序由芳族醛与（硫代）巴比妥酸的最初的Knoevenagel缩合组成，然后第二个当量的（硫代）巴比妥酸衍生物的迈克尔加成，然后由UB催化的Williamson环醚化提供产物。

  DOI：

  10.1016/j.tet.2013.06.030

文献信息

• Molecular Iodine-Catalysed Tandem Synthesis of Oxospirotricyclic Furopyrimidines in Water
  作者：Mohammad Bagher Teimouri、Peyman Akbari-Moghaddam

  DOI：10.3184/174751916x14568468874639

  日期：2016.4

  A simple, efficient and high yielding one-pot protocol for the synthesis of oxospirotricyclic furobarbiturates was developed by pseudo three-component domino coupling of barbituric acids and various benzaldehydes in water, catalysed by molecular iodine.

  在分子碘催化下，通过巴比妥酸和各种苯甲醛在水中的伪三组份多米诺偶联，开发了一种简单、高效、高产的单锅合成氧代三环呋喃巴比妥酸盐的方法。
• New Strategy for the Synthesis of 5-Aryl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)-pentaones and Their Sulfur Analogues
  作者：Mohammad Jalilzadeh、Nader Noroozi Pesyan

  DOI：10.5012/bkcs.2011.32.9.3382

  日期：2011.9.20

  Reaction of barbituric acid (BA), 1,3-dimethyl barbituric acid (DMBA) and 2-thiobarbituric acid (TBA) with cyanogen bromide and aldehydes in the presence of L-(+)-tartaric acid afforded a new route for the synthesis of stable heterocyclic 5-aryl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)pentaones which is a dimeric form of barbiturate (uracil and thiouracil derivative)

  在 L-(+)-酒石酸存在下，巴比妥酸 (BA)、1,3-二甲基巴比妥酸 (DMBA) 和 2-硫代巴比妥酸 (TBA) 与溴化氰和醛的反应为合成稳定的 5-芳基-1H-杂环提供了一条新途径、1'H-螺[呋喃并[2,3-d]嘧啶-6,5'-嘧啶]2,2',4,4',6'(3H,3'H,5H)-五酮，它是巴比妥酸（尿嘧啶和硫尿嘧啶衍生物）的二聚体形式。在与 1,3-二乙基硫代巴比妥酸（DETBA）的反应中，在相同条件下得到了克诺文纳格尔缩合物，然后得到了迈克尔加合物。通过 $^1H$ NMR、$^13}C$ NMR、傅立叶变换红外光谱和质量分析进行了结构阐释。讨论了其形成机理。
• Electrocatalytic and chemical assembling of N,N′-dialkylbarbituric acids and aldehydes: efficient cascade approach to the spiro-[furo[2,3-d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′-(1′H,3H,3′H)-pentone framework
  作者：Anatolii N. Vereshchagin、Michail N. Elinson、Evgeniya O. Dorofeeva、Tatiana A. Zaimovskaya、Nikita O. Stepanov、Sergey V. Gorbunov、Pavel A. Belyakov、Gennady I. Nikishin

  DOI：10.1016/j.tet.2011.11.057

  日期：2012.1

  Electrocatalytic assembling of aldehydes and N,N'-dialkylbarbituric acids leads to selective and efficient formation of substituted 1,5-dihydro-2H,2'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'-(1'H,3H,3'H)-pentones in 70-85% yields as a result of the complex cascade process. The electrocatalytic process smoothly proceeds with aromatic aldehydes bearing both electron-donating and electron-withdrawing groups, and allows for the selective and efficient one-step formation of spirobarbiturates containing furo[2,3-d]pyrimidine scaffold, which are a perspective class of compounds with prominent pharmacological and physiological activity. The application of the effective electrocatalytic cascade method to the formation of medicinally relevant spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'-(1'H,3H,3'H)-pentones is also beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel, facile and environmentally benign synthetic concept for electrocatalytic cascade reaction strategy. (C) 2011 Elsevier Ltd. All rights reserved.
• Cascade assembly of N,N′-dialkylbarbituric acids and aldehydes: a simple and efficient one-pot approach to the substituted 1,5-dihydro-2H,2′H-spiro(furo[2,3-d]pyrimidine-6,5′-pyrimidine)-2,2′,4,4′,6′(1′H,3H,3′H)-pentone framework
  作者：Michail N. Elinson、Anatolii N. Vereshchagin、Nikita O. Stepanov、Pavel A. Belyakov、Gennady I. Nikishin

  DOI：10.1016/j.tetlet.2010.10.041

  日期：2010.12

  Cascade assembly of N,N'-dialkylbarbituric acids and aldehydes in the presence of bromine leads to the selective and efficient formation of substituted 1,5-dihydro-2H,2'H-spiro(furo[2,3-d]pyrimidine-6,5'-pyrimidine)-2,2',4,4',6'-(1'H,3H,3'H)-pentones in 70-88% yields via a complex cascade process. Spirobarbiturates containing the furo[2,3-d]pyrimidine framework are a class of compounds with interesting pharmacological and physiological activity. (C) 2010 Elsevier Ltd. All rights reserved.
• 10.3390/molecules29133178
  作者：Zhang, Yue、Mi, Yu-Hang、Wang, Kuo、Zhao, Hong-Wu

  DOI：10.3390/molecules29133178

  日期：——