5-(4-chlorophenyl)-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 | 1260431-67-1

• 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: 5-(4-chlorophenyl)-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
• 英文别名: 5'-(4-chlorophenyl)-1,1',3,3'-tetramethylspiro[1,3-diazinane-5,6'-5H-furo[2,3-d]pyrimidine]-2,2',4,4',6-pentone
• CAS: 1260431-67-1
• 化学式: C₁₉H₁₇ClN₄O₆
• 分子量: 432.82
• InChiKey: MKJLHERVDDMRME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  30
• 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：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 urotropine-bromine complex 作用下， 以 水 为溶剂， 反应 4.0h， 生成 5-(4-chlorophenyl)-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
  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。
• 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.
• Urotropine–bromine promoted synthesis of functionalized oxaspirotricyclic furopyrimidines via a domino Knoevenagel condensation/Michael addition/α-bromination/Williamson cycloetherification sequence in water
  作者：Mohammad Bagher Teimouri、Peyman Akbari-Moghaddam、Mahnaz Motaghinezhad

  DOI：10.1016/j.tet.2013.06.030

  日期：2013.8

  5′-pyrimidine] derivatives has been developed by a one-pot pseudo three-component domino coupling of aromatic aldehydes and (thio)barbituric acids in the presence of urotropine–bromine (UB) complex in water at room temperature. The reaction sequence consists of an initial Knoevenagel condensation of aromatic aldehydes with (thio)barbituric acids, followed by Michael addition of the second equivalent of

  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。