2,4-dimethyl-11-nitro-4,12b-dihydro-1H,7H-chromeno[4',3'-4,5]pyrano[2,3-d]pyrimidine-1,3(2H)-dione | 1092973-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃嘧啶类
• 英文名称: 2,4-dimethyl-11-nitro-4,12b-dihydro-1H,7H-chromeno[4',3'-4,5]pyrano[2,3-d]pyrimidine-1,3(2H)-dione
• 英文别名: 4,6-Dimethyl-16-nitro-8,12-dioxa-4,6-diazatetracyclo[8.8.0.02,7.013,18]octadeca-2(7),9,13(18),14,16-pentaene-3,5-dione
• CAS: 1092973-10-8
• 化学式: C₁₆H₁₃N₃O₆
• 分子量: 343.296
• InChiKey: GINGSYJKYQVALB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-dimethyl-5-{[5-nitro-2-(2-propynyloxy)phenyl]methylene}-2,4,6(1H,3H,5H)-pyrimidinetrione 在 copper(l) iodide 作用下， 以 水 为溶剂， 反应 6.0h， 以81%的产率得到2,4-dimethyl-11-nitro-4,12b-dihydro-1H,7H-chromeno[4',3'-4,5]pyrano[2,3-d]pyrimidine-1,3(2H)-dione
  参考文献：
  名称：

  Intramolecular hetero-Diels–Alder reaction of 1-oxa-1,3-butadienes with terminal acetylenes in aqueous media using CuI

  摘要：

  A new method for the preparation of tetracyclic uracils (oxa-helicene) 4 was developed. The intramolecular hetero-Diels-Alder reaction of 1-oxa-1,3-butadiene 3 and an unactivated alkyne in the presence of CuI led to tetracyclic uracils 4 in aqueous media with good yields. The 1-oxa-1,3-butadiene 3 was prepared through Knoevenagel reaction of O-propargylated salicylaldehyde derivatives and barbituric acid or 1,3-dimethylbarbituric acid. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.08.056

文献信息

• Zirconium oxide (NP) - ionic liquid as an efficient media for the domino Knoevenagel hetero Diels-Alder reaction with unactivated alkynes
  作者：Saeed Balalaie、Ali Poursaeed、Malihe Javan Khoshkholgh、Hamid Reza Bijanzadeh、Eckardt Wolf

  DOI：10.1016/j.crci.2011.12.002

  日期：2012.4

  Immobilized ZrO 2 -nanopowder (NP) in ionic liquid and different organic solvents was used as a suitable Lewis-acid for the synthesis of polycyclic heterocycles which contains pyran-based skeletons. Reaction of O -propargylated salicylaldehyde with active methylene compounds in the presence of ZrO 2 -NP in ionic liquid proceeds via domino Knoevenagel hetero Diels-Alder reaction of unactivated alkynes

  摘要 以离子液体和不同有机溶剂中的固定化ZrO 2 -纳米粉体(NP)作为合适的路易斯酸，用于合成含有吡喃基骨架的多环杂环。在离子液体中，在 ZrO 2 -NP 存在下，O-炔丙基化水杨醛与活性亚甲基化合物的反应通过未活化炔烃的多米诺 Knoevenagel 杂 Diels-Alder 反应进行，以构建吡喃骨架。与不同离子液体和有机溶剂的比较表明，1-丁基-3-甲基咪唑硝酸盐[bmim][NO 3 ]反应时间短，收率高，效果最好。在这些条件下进行反应具有收率高、反应时间短和易于后处理等优点。
• Trifluoroethanol as an efficient reaction media for the synthesis of pyran skeleton through domino Knoevenagel–hetero-Diels–Alder reaction with non-activated alkynes
  作者：Saeed Balalaie、Javad Azizian、Abolghasem Shameli、Hamid Reza Bijanzadeh

  DOI：10.1007/s13738-014-0521-8

  日期：2015.4

  AbstractTrifluoroethanol as an efficient media for the domino Knoevenagel–hetero-Diels–Alder reaction of O-propargyloxy benzaldehydes as non-activated terminal alkynes with some active methylene compounds has been described. Short reaction time, easy work-up, good to high yields, and mild reaction conditions are advantages of this new media. Graphical Abstract

  摘要已经描述了三氟乙醇作为O-炔丙氧基苯甲醛作为未活化的末端炔的多米诺Knoevenagel-杂Diels-Alder反应的有效介质，并与一些活性亚甲基化合物进行了反应。这种新介质的优点是反应时间短，易于后处理，收率高至高以及反应条件温和。 图形概要
• CuI–Ionic Liquids as Efficient Reaction Media for the Synthesis of Pyran Skeleton via Domino Knoevenagel–Hetero–Diels–Alder Reaction with Unactivated Alkynes
  作者：Saeed Balalaie、Javad Azizian、Abolghasem Shameli、Hamid Reza Bijanzadeh

  DOI：10.1080/00397911.2012.669874

  日期：2013.7.3

  Abstract The article describes ionic liquids [bmim][NO3] in the presence of 30% mol CuI as efficient media for the domino Knoevenagel–hetero–Diels–Alder reaction of o-propargyloxy benzaldehydes as unactivated terminal alkynes with some active methylene compounds. Short reaction time, easy workup, good to excellent yields, and mild conditions are advantages of this new media. Supplemental materials

  摘要 本文描述了在 30% mol CuI 存在下离子液体 [bmim][NO3] 作为多米诺 Knoevenagel-hetero-Diels-Alder 反应的有效介质，邻炔氧基苯甲醛作为未活化的末端炔烃与一些活性亚甲基化合物。反应时间短、后处理容易、产率高到极好、条件温和是这种新培养基的优点。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Synthesis of novel annulated uracils via domino Knoevenagel-hetero-Diels–Alder reaction in aqueous media
  作者：Malihe Javan Khoshkholgh、Saeed Balalaie、Hamid Reza Bijanzadeh、Frank Rominger、Jürgen H. Gross

  DOI：10.1016/j.tetlet.2008.09.079

  日期：2008.12

  An efficient synthesis of tetracyclic uracil derivatives (polycyclic pyrans) is achieved via domino Knoevenagel-hetero-Diels–Alder reactions of O-propargylated salicylaldehyde derivatives with 1,3-dimethylbarbituric acid in water as solvent in the presence of CuI. The products are formed in good yields.

  在CuI存在下，通过O-炔丙基化水杨醛衍生物与1,3-二甲基巴比妥酸的多米诺Knoevenagel-杂Diels-Alder反应，可以在水中有效地合成四环尿嘧啶衍生物（多环吡喃）。该产品以高收率形成。
• Intramolecular hetero-Diels–Alder reaction of 1-oxa-1,3-butadienes with terminal acetylenes in aqueous media using CuI
  作者：Malihe Javan Khoshkholgh、Saeed Balalaie、Rolf Gleiter、Frank Rominger

  DOI：10.1016/j.tet.2008.08.056

  日期：2008.11

  A new method for the preparation of tetracyclic uracils (oxa-helicene) 4 was developed. The intramolecular hetero-Diels-Alder reaction of 1-oxa-1,3-butadiene 3 and an unactivated alkyne in the presence of CuI led to tetracyclic uracils 4 in aqueous media with good yields. The 1-oxa-1,3-butadiene 3 was prepared through Knoevenagel reaction of O-propargylated salicylaldehyde derivatives and barbituric acid or 1,3-dimethylbarbituric acid. (C) 2008 Published by Elsevier Ltd.