4,4′‐(1,4‐phenylene)bis(2‐amino‐7,7‐dimethyl‐5‐oxo‐5,6,7,8‐tetrahydro‐4H‐chromene‐3‐carbonitrile) | 309927-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4′‐(1,4‐phenylene)bis(2‐amino‐7,7‐dimethyl‐5‐oxo‐5,6,7,8‐tetrahydro‐4H‐chromene‐3‐carbonitrile)
• 英文别名: 4,4′‐(1,4‐phenylene)bis(2‐amino‐3‐cyano‐7,7‐dimethyl‐5‐oxo‐4H‐5,6,7,8‐tetrahydrobenzo[b]pyran)；2-amino-4-(4-(2-amino-3-cyano-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromen-4-yl)phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；4,4’-(1,4-phenylene)bis(2-amino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile)；4,4′-(1,4-Phenylene)bis(2-amino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile)；4,4'-(1,4-phenylene)bis(2-amino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile)；4,4'-(1,4-phenylene)bis(2-amino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4Hchromene-3-carbonitrile)；2-amino-4-[4-(2-amino-3-cyano-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromen-4-yl)phenyl]-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• CAS: 309927-27-3
• 化学式: C₃₀H₃₀N₄O₄
• mdl: MFCD01466459
• 分子量: 510.593
• InChiKey: KKYKZLCNFIFHIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-羟基-5,5-二甲基环己-2-烯-1-酮 、 对苯二甲醛 、 丙二腈 在 iron(III) oxide 、 ammonium acetate 作用下， 以 水 为溶剂， 以87%的产率得到4,4′‐(1,4‐phenylene)bis(2‐amino‐7,7‐dimethyl‐5‐oxo‐5,6,7,8‐tetrahydro‐4H‐chromene‐3‐carbonitrile)
  参考文献：
  名称：

  Water dispersed magnetic nanoparticles (H2O-DMNPs) of γ-Fe2O3 for multicomponent coupling reactions: a green, single-pot technique for the synthesis of tetrahydro-4H-chromenes and hexahydroquinoline carboxylates

  摘要：

  Water dispersed magnetic nanoparticles (DMNPs) of gamma-Fe2O3 represent a simple and green catalyst for the rapid three-component synthesis of tetrahydro-4H-chromene and hexahydroquinoline carboxylate skeletons via single-pot domino Knoevenagel-Michael-cyclization reactions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.048

文献信息

• An efficient and practical synthesis of specially 2-amino-4H-pyrans catalyzed by C4(DABCO-SO3H)2·4Cl
  作者：Omid Goli-Jolodar、Frahad Shirini、Mohadeseh Seddighi

  DOI：10.1016/j.dyepig.2016.06.001

  日期：2016.10

  A mild, simple and convenient procedure for the synthesis of spiro-oxindole heterocycles containing fused 4H-pyran ring and also bis-2-amino-4H-pyrans derivatives was described using C4(DABCO-SO3H)2·4Cl as a nano, efficient, cheap, and reusable catalyst under mild and homogeneous conditions.

  使用C 4（DABCO-SO 3 H）2 · 4Cl描述了一种温和，简单，方便的方法，用于合成含有稠合的4 H-吡喃环以及双-2-氨基-4 H-吡喃衍生物的螺-羟吲哚杂环。在温和均匀的条件下作为一种纳米，高效，廉价且可重复使用的催化剂。
• An approach to the synthesis and characterization of HMS/Pr-Rh-Zr as efficient catalyst for synthesis of tetrahydrobenzo[b]pyran and 1,4-dihydropyrano[2,3-c]pyrazole derivatives
  作者：Sahar Abdolahi、Maryam Hajjami、Fatemeh Gholamian

  DOI：10.1007/s11164-021-04411-z

  日期：2021.5

  HMS/Pr-Rh-Zr was successfully synthesized. Also the catalytic activity of HMS/Pr-Rh-Zr is investigated for the synthesis of tetrahydrobenzo[b]pyran derivatives from reaction between aldehyde, malononitrile, dimedone in PEG at 80 °C and synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives from reaction between aldehyde, ethyl acetoacetate, malononitrile and hydrazine hydrate in H2O:EtOH at 35 °C

  本研究的目的是基于六角形介孔二氧化硅的介孔催化剂的合成。HMS支撑物具有出色的特性，例如易于合成，高表面积，大孔体积和虫孔。这些独特的特性似乎将其用作合成非均相催化剂的载体。通过HMS的功能化和将Zr-罗丹宁复合物固定到功能化的HMS中，获得了HMS / Pr-Rh-Zr。FT-IR，XRD，TGA，SEM，EDX，77 K氮气吸附-脱附和ICP技术表征了新型合成催化剂（HMS / Pr-Rh-Zr）。这些技术证实了成功地合成了HMS / Pr-Rh-Zr的非均相催化剂。还研究了HMS / Pr-Rh-Zr的催化活性，用于由醛之间的反应合成四氢苯并[b]吡喃衍生物。在35°C下2 O：EtOH。这些结果证实了HMS / Pr-Rh-Zr表现出良好的催化性能。此外，合成的非均相催化剂可以在反应后回收并重复使用几次而没有任何明显的活性损失。还研究了HMS / Pr-Rh-Zr的锆浸出，因此催化剂的金属浸出非常低。
• Perchloric acid modified-cellulose: a versatile, novel and biodegradable heterogeneous solid acid catalyst for single-pot synthesis of novel bis-pyran annulated heterocyclic scaffolds under solvent-free conditions
  作者：Tabassum Khan、Zeba N. Siddiqui

  DOI：10.1039/c4nj00529e

  日期：——

  the synthesis of novel bis-pyran annulated heterocyclic scaffolds (4a–r) using cellulose–perchloric acid (CPA) as an eco-friendly, biodegradable and recyclable catalyst in excellent yields under solvent-free conditions. Other remarkable features of this environmentally benign protocol are short reaction time, a wide range of functional group tolerance, use of inexpensive heterogeneous catalyst, and

  已经开发了一种单罐多组分，绿色高效的方案，用于使用纤维素-高氯酸（CPA）作为生态友好，可生物降解和可回收利用的新型双吡喃环杂环支架（4a-r）在无溶剂条件下，催化剂的收率极高。与常规方法相比，该环境友好方案的其他显着特征是反应时间短，官能团耐受性范围广，使用廉价的非均相催化剂以及通过简单的实验和后处理程序即可获得高收率的产品。纤维素-HClO 4（CPA）催化剂的特点是使用FTIR，粉末XRD和SEM-EDX分析。通过TG / DTA表征技术评估催化剂的稳定性。催化剂可以循环使用几次，但催化活性会略有下降。
• One-pot synthesis of 2-amino-3-cyano-4<i>H</i>-pyrans and pyran-annulated heterocycles using sodium citrate as an organo-salt based catalyst in aqueous ethanol
  作者：Aiborlang Thongni、Pynskhemborlang T. Phanrang、Arup Dutta、Rishanlang Nongkhlaw

  DOI：10.1080/00397911.2021.1998535

  日期：2022.1.2

  shorter reaction time, utilization of eco-friendly solvents, operational simplicity, mild reaction conditions, and maximum product yield. Moreover, the use of sodium citrate as an easily available, cheap and benign catalyst plays a pivotal role from a green perspective, considering its high recyclability and easy recovery. Therefore, this present methodology offers numerous possibilities in terms of large-scale

  摘要 柠檬酸钠作为一种高效催化剂被开发用于合成官能化的 2-氨基-3-氰基-4 H-吡喃和吡喃环化杂环。该方法涉及芳香醛、丙二腈和 1,3-二羰基化合物与 EtOH 的一锅三组分反应：H 2O (1:1 v/v) 在室温下作为溶剂。该协议具有几个优点，例如更短的反应时间、环保溶剂的利用、操作简单、反应条件温和和产品收率最高。此外，考虑到柠檬酸钠的高可回收性和易回收性，从绿色角度来看，柠檬酸钠作为一种易于获得、廉价和良性的催化剂发挥着关键作用。因此，本方法在大规模工业合成或应用于众多有机转化方面提供了许多可能性。此外，还对产物4aa形成的机理途径进行了理论研究，以确定柠檬酸钠对DFT法反应可行性的催化作用，使用B3LYP泛函。
• 1-Methylimidazolium tricyanomethanide {[HMIM]C(CN)3} as a nano structure and reusable molten salt catalyst for the synthesis of tetrahydrobenzo[b]pyrans via tandem Knoevenagel-Michael cyclocondensation and 3,4-dihydropyrano[c]chromene derivatives
  作者：Mohammad Ali Zolfigol、Neda Bahrami-Nejad、Fatemeh Afsharnadery、Saeed Baghery

  DOI：10.1016/j.molliq.2016.06.069

  日期：2016.9

  An expeditious, experimentally simple and rapid 1-methylimidazolium tricyanomethanide [HMIM]C(CN)3} nano molten salt (NMS) catalyzed tandem Knoevenagel-Michael cyclocondensation procedure for the synthesis of tetrahydrobenzo[b]pyrans was described via reaction between dimedone, aromatic aldehyde and malononitrile under solvent-free conditions at room temperature. Furthermore, 3,4-dihydropyrano[c]chromene

  通过二甲酮之间的反应，描述了一种快速，实验简单且快速的三氰基甲基1-甲基咪唑鎓[HMIM] C（CN）3 }纳米熔融盐（NMS）催化串联Knoevenagel-Michael环缩合反应合成四氢苯并[ b ]吡喃的方法，室温下在无溶剂条件下的芳族醛和丙二腈。此外，在相同条件下，以[HMIM] C（CN）3 } NMS为催化量，通过4-羟基香豆素，芳香醛和丙二腈的缩合反应合成了3,4-二氢吡喃并[ c ]色烯衍生物。