2H-[1,3]dioxolo[4',5':6,7]chromeno[2,3-d]pyrimidine-2,4(3H)-dione | 141266-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2H-[1,3]dioxolo[4',5':6,7]chromeno[2,3-d]pyrimidine-2,4(3H)-dione
• 英文别名: 2,13,15-Trioxa-4,6-diazatetracyclo[8.7.0.03,8.012,16]heptadeca-1(17),3,8,10,12(16)-pentaene-5,7-dione
• CAS: 141266-49-1
• 化学式: C₁₂H₆N₂O₅
• 分子量: 258.19
• InChiKey: SZUZKPOPKYFTAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-<5-bromo-1,3-benzodioxol-6-yl>methylenepyrimidin-2,4,6(1H,3H)-trione 在 sodium chloride 作用下， 反应 0.08h， 以98%的产率得到2H-[1,3]dioxolo[4',5':6,7]chromeno[2,3-d]pyrimidine-2,4(3H)-dione
  参考文献：
  名称：

  Synthesis and mechanism of formation of oxadeazaflavines by microwave thermal cyclization of ortho-halobenzylidene barbiturates

  摘要：

  The thermal cyclization reaction of o-halobenzylidene barbiturates was developed as an efficient and simple method for the preparation of oxadeazaflavines. The use of solid state reaction conditions with microwave irradiation afforded the products in 5 min with 47 to 98% yield. Experimental synthetic results and thermogravimetric reaction analyses agree with the molecular modeling mechanism simulation, indicating that this reaction occurs through an intramolecular hetero-Diels-Alder cyclization followed by fast re-aromatization.

  DOI：

  10.1590/s0103-50532011001100012

文献信息

• Synthesis of Oxadeazaflavines from Barbituric Acid and Aromatic Aldehydes
  作者：José Daniel Figueroa-Villar、Elizabete Rangel Cruz、Nedina Lucia dos Santos

  DOI：10.1080/00397919208021101

  日期：1992.4

  2H-Chromeno[2,3-d]-pyrimidine-2,4(3H)-diones were prepared directly from barbituric acid and salicylaldehydes or by thermal cyclization of the condensation product of barbituric acid and 6-bromopiperonal.