2-氨基-7,7-甲基-4-(3-硝基苯基)-5-氧代-5,6,7,8-四氢-4H-色烯-3-腈 | 144036-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-7,7-甲基-4-(3-硝基苯基)-5-氧代-5,6,7,8-四氢-4H-色烯-3-腈
• 中文别名: 2-氨基-7,7-二甲基-4-(3-硝基苯基)-5-氧代-5,6,7,8-四氢-4H-亚甲基-3-腈
• 英文名称: 2-amino-3-cyano-5,6,7,8-tetrahydro-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-4H-benzopyran
• 英文别名: 2‐amino‐4‐(3‐nitrophenyl)‐7,7‐dimethyl‐5‐oxo‐5,6,7,8‐tetrahydro‐4H‐chromene‐3‐carbonitrile；2‑amino‑3‑cyano‑7,7‑dimethyl‑4‑(3‑nitrophenyl)‑5‑oxo‑4H‑5,6,7,8‑tetrahydro benzopyran；2-amino-7,7-dimethyl-5-oxo-4-(3-nitrophenyl)-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitrile；2-amino-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-benzopyran-3-carbonitrile；2-amino-7,7-dimethyl-4-(3-nitro-phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-4-(3-nitrophenyl)-6,6,8,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile；2-amino-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• CAS: 144036-36-2
• 化学式: C₁₈H₁₇N₃O₄
• 分子量: 339.351
• InChiKey: VEQGLLBDKJRYDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氨基-7,7-甲基-4-(3-硝基苯基)-5-氧代-5,6,7,8-四氢-4H-色烯-3-腈 在 水 、 对甲苯磺酸 作用下， 反应 5.5h， 以85%的产率得到7,7-dimethyl-4-(3-nitro-phenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydro-quinoline-3-carbonitrile
  参考文献：
  名称：

  Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media

  摘要：

  A green and highly efficient protocol has been developed for the synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and a 1,3-diketo compound using nano structured ZnO as the catalyst in aqueous alcoholic medium. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran derivatives in aqueous medium applying p-TSOH as the right catalyst source. A wide spectrum of functional groups was tolerated in both the developed synthetic protocols with good to excellent yield of the targeted molecules. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.086
• 作为产物：
  描述：

  间硝基苯甲醛 以 水 为溶剂， 反应 0.34h， 生成 2-氨基-7,7-甲基-4-(3-硝基苯基)-5-氧代-5,6,7,8-四氢-4H-色烯-3-腈
  参考文献：
  名称：

  Catalyst-Free Cascade Synthesis of Densely Functionalized Chromenes in Water

  摘要：

  已开发出一种快速且环保的通用方案，用于在水中通过级联Knoevenagel-Michael-分子内环化合成2-氨基-3-氰基-4H-香豆素。通过简单的过滤技术获得了纯固体产物。在室温下，无水催化剂的水相反应导致高产物收率。

  DOI：

  10.14233/ajchem.2019.22191

文献信息

• Synthesis of functionalized chromene and spirochromenes using l -proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
  作者：Sakkani Nagaraju、Banoth Paplal、Kota Sathish、Santanab Giri、Dhurke Kashinath

  DOI：10.1016/j.tetlet.2017.09.060

  日期：2017.11

  commercially cheap l-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, l-proline and melamine (3:1 ratio;

  使用便宜的1-脯氨酸和三聚氰胺开发了一种有效且可循环使用的均相催化剂，用于在室温下通过多组分反应合成色烯和螺环色酮（螺并辛多烯）。为了使用各种α-氨基酸和芳族胺作为供体-受体对，进行系统研究以实现所需的反应性和催化剂的可回收性。在筛选的组合中，l脯氨酸和三聚氰胺（3：1的比例；占总重量的3 mol％）被认为是最佳的催化剂，可以在室温下非常短的时间内（1-15分钟）以优异的产率（高达99％）提供所需的产品在DMSO中作为溶剂。通过添加EtOAc来回收催化剂，并且在不损失催化活性的情况下重复使用多达5个循环。
• 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。
• 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。
• Preparation, characterization, and use of poly(vinylpyrrolidonium) hydrogen phosphate ([PVP-H]H2PO4) as a new heterogeneous catalyst for efficient synthesis of 2-amino-tetrahydro-4H-pyrans
  作者：Farhad Shirini、Omid Goli-Jolodar、Maryam Akbari、Mohadeseh Seddighi

  DOI：10.1007/s11164-015-2312-y

  日期：2016.5

  A novel Brønsted solid acid named poly(vinylpyrrolidonium) hydrogen phosphate ([PVP-H]H2PO4) has been prepared by using H3PO4 and poly(vinylpyrrolidone) as green and commercially available reagents. The prepared reagent was characterized using a series of techniques including Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), X-ray diffraction (XRD) analysis, energy-dispersive X-ray analysis (EDAX), pH analysis, and Hammett acidity function. The mentioned solid acid with wide acidic functional group sites can be utilized as a highly efficient, heterogeneous, and reusable catalyst for preparation of 2-amino-3-cyano-5-oxo-5,6,7,8-tetrahydro-4H-benzopyrans using aldehydes, dimedone, and malononitrile. Also, this catalyst can be reused for several times without loss of catalytic activity.

  一种新型布朗斯台德固体酸名为聚乙烯基吡咯烷酮磷酸氢盐（[PVP-H]H2PO4），采用绿色且商业上可获得的试剂H3PO4和聚乙烯基吡咯烷酮制备。制备的试剂通过一系列技术进行了表征，包括傅里叶变换红外光谱（FT-IR）、热重分析（TGA）、扫描电子显微镜（SEM）、X射线衍射（XRD）分析、能散X射线分析（EDAX）、pH分析和哈米特酸度函数。这种具有广泛酸性功能团位的固体酸可作为高效、非均相和可重复使用的催化剂，用于醛、双甲酮和丙二腈制备2-氨基-3-氰基-5-氧-5,6,7,8-四氢-4H-苯并吡喃。此外，该催化剂可多次重复使用而不会损失催化活性。
• [DMImd-DMP]: A highly efficient and reusable catalyst for the synthesis of 4H-benzo[b]pyran derivatives
  作者：Mohamed Abdenour Redouane、Naima Khiri-Meribout、Saida Benzerka、Abdelmadjid Debache

  DOI：10.1515/hc-2019-0025

  日期：2019.12.31

  Abstract A series of substituted 4H-pyrans derivatives were synthesized by a one-pot, multi-component reaction of aromatic aldehydes, malononitrile, and pyrazolone derivatives or active methylene carbonyl compounds such as dimedone, in the presence of 1,3-dimethyl imidazolium dimethyl phosphate [DMImd-DMP] as a catalyst in aqueous ethanol. Recyclability of the catalyst, high yields, simple product

  摘要 以芳香醛、丙二腈和吡唑啉酮衍生物或活性亚甲基羰基化合物如二甲酮为原料，在1,3-二甲基咪唑鎓二甲基吡啶存在下，通过一锅多组分反应合成了一系列取代的4H-吡喃衍生物。磷酸盐 [DMImd-DM​​P] 作为乙醇水溶液中的催化剂。催化剂的可回收性、高产率、简单的产品分离和高原子经济性是该协议值得注意的方面。