5-(1H-indol-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]-pyrimidine-2,4(3H,5H)-dione | 1441019-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(1H-indol-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]-pyrimidine-2,4(3H,5H)-dione
• 英文别名: 5-(1H-indol-3-yl)-1,3-dimethyl-1,5-dihydro-2H-chromeno[2,3-d]pyrimidine-2,4(3H)-dione；5-(1H-indol-3-yl)-1,3-dimethyl-5H-chromeno[2,3-d]pyrimidine-2,4-dione
• CAS: 1441019-57-3
• 化学式: C₂₁H₁₇N₃O₃
• 分子量: 359.384
• InChiKey: KJWHHIFYJOWLTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 1,3-二甲基巴比妥酸 、 水杨醛 在 trypsin immobilized via NHCS - dendrimer on Fe₃O₄(at)SiO₂ 作用下， 以 neat (no solvent) 为溶剂， 反应 0.15h， 以98%的产率得到5-(1H-indol-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]-pyrimidine-2,4(3H,5H)-dione
  参考文献：
  名称：

  Fe3O4@SiO2@D-NHCS-Tr作为一种高效且可重复使用的催化剂，用于在无溶剂条件下通过多组分反应合成吲哚-3-基-4H-色烯

  摘要：

  Fe 3 O 4 @SiO 2 @D-NHCS-Tr 被用作吲哚衍生物、水杨醛和活性亚甲基化合物在无溶剂条件下的三组分反应中合成吲哚-3-基-的有效催化剂。 4 H-色烯衍生物。该方法的特点是反应条件绿色、易分离、催化剂环保经济、反应时间短、收率高。

  DOI：

  10.1002/jhet.4258

文献信息

• New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4 <i>H</i> ‐chromenes using magnetic nanoparticle catalyst
  作者：Hassan Ghavidel、Behrooz Mirza、Somayeh Soleimani‐Amiri、Mohammadreza Manafi

  DOI：10.1002/jccs.201900554

  日期：2020.10

  A green synthesis of functionalized 4H‐chromenes using one‐pot, three‐component reaction of salicylaldehyde (1), active methylene (2), and carbon‐based nucleophile (3) using Fe3O4@CONa nanoparticles in water has been performed at 60°C. The Fe3O4@CONa nanoparticle as an efficient, green, and magnetically reusable heterogeneous catalyst was applied in these reactions up to the nine runs. Green catalyst

  使用Fe 3 O 4 @CONa纳米粒子在水中通过水杨醛（1），活性亚甲基（2）和碳基亲核试剂（3）的一锅，三组分反应进行绿色合成功能化4 H-色烯。在60°C下进行。铁3 O 4作为一种有效，绿色和可磁重复使用的多相催化剂，CONa纳米颗粒被用于这些反应中，直到九次运行。发现绿色催化剂和溶剂，较短的反应时间，较高的产品收率以及简单的后处理程序是该方法的一些优点。密度泛函理论计算应用于一锅，三组分反应机理的全包感知。最多的反应是通过以下途径进行的：（a）2比1的亲核加成；（b）闭环，脱水；（c）3（2-萘酚，4-羟基香豆素）亲核取代为中间体。有时将机制突变为：（a）将3（吲哚，2-甲基吲哚）亲核加成1，脱水；（b）将2亲核加成；（c）闭环和脱水。前沿的分子轨道，NBO分析，反应物的分子静电势和中间体证实了该提议机制。理论研究可能有助于挑选合适的反应物。
• Nanocrystalline and Reusable ZnO Catalyst for the Assembly of Densely Functionalized 4<i>H</i>-Chromenes in Aqueous Medium via One-Pot Three Component Reactions: A Greener “NOSE” Approach
  作者：Partha Pratim Ghosh、Asish R. Das

  DOI：10.1021/jo400763z

  日期：2013.6.21

  An ecofriendly, One-pot, three component ZnO nanoparticles-mediated synthesis of 4H-chromene in water under thermal condition has been described. The highly product-selective three component electrophilic reaction of 2-hydroxybenzaldehyde with an active methylene compound and another carbon-based varied nature of nucleophile has been developed by a reversible alkylation procedure using greener "NOSE" approach. Greenness of the process was well instituted, as water was used both;as reaction media as well as medium for the synthesis of catalyst. In these reactions, the use of nano-ZnO as a catalyst was documented to be crucial for rendering the reactions possible in water media, while replacing nano-ZnO with other acids or bases resulted in the generation of too many side products. The catalyst can be efficiently recycled up to the sixth run, an essential point in the area of green chemistry. The methodology provides cleaner conversion, shorter reaction times, and high selectivity, which make the protocol globally putative. The crystal structures of 4H-chromene, easily produced by a chromatography-free highly product-selective reaction, were explored by means of single crystal X-ray diffraction analysis, and H-bonding arrangements of one signified compound prepared is presented. In optimized mild conditions, the isolated yields are 86-93%.
• <scp> Fe ₃ O ₄ </scp> @ <scp> SiO ₂ </scp> @ <scp>D‐NHCS‐Tr</scp> as an efficient and reusable catalyst for the synthesis of <scp> indol‐3‐yl‐4 <i>H</i> </scp> ‐chromene via a multi‐component reaction under solvent‐free conditions
  作者：Robabeh Baharfar、Sahar Peiman、Behrooz Maleki

  DOI：10.1002/jhet.4258

  日期：2021.6

  Fe3O4@SiO2@D-NHCS-Tr was used as an efficient catalyst in the three-component reaction between indole derivatives, salicylaldehyde, and active methylene compounds under solvent-free conditions to the synthesis of indol-3-yl-4H-chromene derivatives. The features of this method include the green conditions of the reaction, easy separation, eco-friendly and cost-effectiveness of the catalyst, and high yield in short

  Fe 3 O 4 @SiO 2 @D-NHCS-Tr 被用作吲哚衍生物、水杨醛和活性亚甲基化合物在无溶剂条件下的三组分反应中合成吲哚-3-基-的有效催化剂。 4 H-色烯衍生物。该方法的特点是反应条件绿色、易分离、催化剂环保经济、反应时间短、收率高。