11-bromo-2,4-dimethyl-4,12b-dihydro-1H,7H-chromeno[4',3'-4,5]pyrano[2,3-d]pyrimidine-1,3(2H)-dione | 1092973-07-3

• 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: 11-bromo-2,4-dimethyl-4,12b-dihydro-1H,7H-chromeno[4',3'-4,5]pyrano[2,3-d]pyrimidine-1,3(2H)-dione
• 英文别名: 16-Bromo-4,6-dimethyl-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: 1092973-07-3
• 化学式: C₁₆H₁₃BrN₂O₄
• 分子量: 377.194
• InChiKey: PCUQYNHTFBOGSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 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：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴-2-(丙基-2-氧基)苯甲醛 在 盐酸 、 6C₃₂H₂₄N₆*12C₆H₁₆N₂*12Pd⁽²⁺⁾*21NO₃^(1-)*57H₂O 作用下， 以 硝基甲烷 、 水 为溶剂， 反应 28.0h， 生成 11-bromo-2,4-dimethyl-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：

  离散的自组装Pd12三角形Orthobicupola笼及其在分子内环加成反应中的应用

  摘要：

  水溶性Pd 12 L 6配位笼TC-1是通过对称四吡啶基供体L与90°对位受体顺式[[Pd（NO 3）2（tmeda）]]配位驱动的自组装合成的[tmeda = N，N，N '，N'-四甲基乙烷-1，2-二胺]。Pd 12 L 6协调组件是具有三角形正斜交形几何形状的协调笼的不常见示例。通过多核NMR光谱，ESI-MS和单晶X射线衍射对其进行了表征。四聚体供体的自组装与顺式阻滞的90°异位受体通常产生三/四/六边形的桶或密闭的立方笼。然而，在当前情况下，供体和受体以不寻常的方式排列以产生正交双体几何形状，其中两个三角形冲天炉共享一个共同的不规则六边形面。该笼子用于在硝基甲烷中进行O-炔丙基化苄基巴比妥酸衍生物的分子内环加成反应。在温和的反应条件下，通过笼催化的[4 + 2]环加成反应以协调一致的方式合成了几种五/四环尿嘧啶衍生物，并具有良好的转化率，而在没有笼TC-1的情况下相似的反应导致

  DOI：

  10.1002/chem.201803039

文献信息

• 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.
• Highly stereo and chemoselective synthesis of tetra and pentacyclic frameworks using Solid-State Melt Reaction (SSMR)
  作者：Manickam Bakthadoss、Govindan Sivakumar

  DOI：10.1016/j.tetlet.2014.01.126

  日期：2014.3

  Benzopyran fused tetra and pentacyclic frameworks have been synthesized by the domino Knoevenagel hetero Diels-Alder (DKHDA) reaction using various 1,3-diones with O-allylated salicylaldehydes and O-propargylated salicylaldehydes in a solvent and catalyst free condition via Solid-State Melt Reaction (SSMR). The reaction requires only a single step operation thus providing potentially bioactive polycyclic heterocycles in high yields. (C) 2014 Elsevier Ltd. All rights reserved.