2-amino-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile | 129354-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-7,7-dimethyl-5-oxo-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitrile；2-amino-4-(2-chlorophenyl)-6,6,8,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile；2-amino-4-(2-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-7,7-dimethyl-4-(2-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-7,7-dimethyl-5-oxo-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-4H-chromen-3-carbonitrile；2-amino-3-cyano-4-(2-chlorophenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydro-benzo[b]pyran；2-amino-4-(2-chlorophenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• CAS: 129354-35-4
• 化学式: C₁₈H₁₇ClN₂O₂
• 分子量: 328.798
• InChiKey: XQKMEIFXCAEVTM-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C
• 沸点：
  538.7±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 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：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以65%的产率得到2-amino-4-(2-chlorophenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  Elnagdi, Mohamed Hilmy; Aal, Fatma Abdel Maksoud Abdel; Yassin, Youssef Mahfouz, Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 6, p. 971 - 976

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯甲醛 在 potassium fluoride dihydrate 作用下， 以 乙醇 为溶剂， 生成 2-amino-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  新型9,9-二甲基-8,12-二氢-9 H-色基[3,2- e ][1,2,4]三唑并[1,5 - c ]嘧啶-11(10 H )-one的合成衍生品

  摘要：

  9,9-二甲基-8,12-二氢-9H-色基[3,2-e][1,2,4]三唑并[1,5-c]嘧啶-11(10H)-one衍生物的合成原甲酸三乙酯或芳香醛与色诺[2,3-d]嘧啶衍生物的反应，其由一水合肼和甲酰亚胺衍生物反应制备。通过 2-氨基-7,7-二甲基-5-氧代-4-芳基-5,6,7,8-四氢-4H-色烯-3-腈衍生物和原甲酸三乙酯的反应合成甲酰亚胺。12-(4-甲氧基苯基)-9,9-二甲基-8,12-二氢-9H-色基[3,2-e][1,2,4]三唑并[1,5-c]嘧啶- 11(10H)-one是通过单晶X射线衍射分析确定的。

  DOI：

  10.3184/174751914x14053476598397

文献信息

• 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。
• Synthesis of Tetrahydrobenzo[<i>b</i>]pyran and Pyrano[2, 3-<i>d</i>]pyrimidinone Derivatives Using Fe₃O₄@Ph-PMO-NaHSO₄ as a New Magnetically Separable Nanocatalyst
  作者：Mahdieh Haghighat、Farhad Shirini、Mostafa Golshekan

  DOI：10.1166/jnn.2019.16032

  日期：2019.6.1

  Immobilized NaHSO₄ on core/shell phenylene bridged periodic mesoporous organosilica magnetic nanoparticles (Fe₃O₄@Ph-PMO-NaHSO₄) as a new acidic magnetically separable nanocatalyst was successfully prepared in three steps: (i) preparation of Fe₃O₄ nanoparticles by a precipitation method, (ii) synthesis of an organic–inorganic periodic mesoporous organosilica structure with phenyl groups on the surface of Fe₃O₄ magnetic nanoparticles (MNPs) and (iii) finally adsorption of NaHSO₄ on periodic mesoporous organosilica (PMO) network. The prepared organic–inorganic magnetic reagent was characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), transmission electron microscopy (TEM), N₂ adsorption–desorption and energy-dispersive X-ray (EDX) techniques. Finally, it was used as a reusable and new catalyst to promote the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives as important biologically active compounds. Eco-friendly protocol, high yields, short reaction times and easy and quick isolation of the products are the main advantages of this procedure.

  在核/壳苯基桥联周期性介孔有机硅磁性纳米颗粒（Fe3O4@Ph-PMO-NaHSO4）上固定化的NaHSO4作为一种新型酸性磁性可分离纳米催化剂成功地通过三个步骤制备而成：（i）通过沉淀法制备Fe3O4纳米颗粒，（ii）合成具有苯基团的有机-无机周期性介孔有机硅结构，将其覆盖在Fe3O4磁性纳米颗粒（MNPs）表面，（iii）最后将NaHSO4吸附在周期性介孔有机硅（PMO）网络上。制备的有机-无机磁性试剂通过傅里叶变换红外光谱（FT-IR）、X射线粉末衍射（XRD）、透射电子显微镜（TEM）、N2吸附-脱附和能谱X射线（EDX）技术进行表征。最后，它被用作可重复使用的新型催化剂，促进四氢苯并[b]吡喃和吡喃并[2,3-d]嘧啶酮衍生物的合成，这些是重要的生物活性化合物。环保的方案、高产率、短反应时间以及产品的易于快速分离是该程序的主要优点。
• Introduction of organic/inorganic Fe₃O₄@MCM-41@Zr-piperazine magnetite nanocatalyst for the promotion of the synthesis of tetrahydro-4<i>H</i>-chromene and pyrano[2,3-<i>d</i>]pyrimidinone derivatives
  作者：Reyhaneh Pourhasan-Kisomi、Farhad Shirini、Mostafa Golshekan

  DOI：10.1002/aoc.4371

  日期：2018.7

  highly dispersed in the tetrahedral environment of silica framework and piperazine is successfully attached to the surface of the nanocatalyst in connection with zirconium. The prepared nanosized reagent (10–30 nm), shows excellent catalytic activity in the synthesis of tetrahydro‐4H‐chromene and pyrano[2,3‐d]pyrimidinone derivatives. All reactions are performed under mild and completely heterogeneous

  哌嗪修饰的Fe 3 O 4 @ MCM-41 @ Zr-MNPs易于制备，并使用傅里叶变换红外光谱（FT-IR），X射线粉末衍射（XRD），N 2吸附-解吸，透射电子显微镜进行表征（ TEM），能量色散X射线（EDX），振动样品磁力法（VSM）和热重分析（TGA）技术。表征结果表明，高度分散在二氧化硅骨架和哌嗪的四面体环境中的Zr可以成功地附着在与锆相关的纳米催化剂表面。制备的纳米级试剂（10–30 nm）在四氢-4 H-色烯和吡喃[2,3- d]嘧啶酮衍生物。所有反应均在温和且完全异质的反应条件下进行，且反应时间短。另一方面，由于其超顺磁性，该催化剂可通过施加外部磁场容易地分离并重复使用多次。
• Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one-pot three-component synthesis of pyran derivatives
  作者：Seyedeh Fatemeh Hojati、Amirhassan Amiri、Nasrin MoeiniEghbali、Sakineh Mohamadi

  DOI：10.1002/aoc.4235

  日期：2018.4

  Polypyrrole (PPY)/Fe3O4/CNT has been synthesized and characterized by FT‐IR, TEM and SEM techniques and its catalytic activity has been evaluated in the synthesis of several series of pyran derivatives. Tetrahydrobenzo[b]pyranes, 4H‐pyran‐3‐carboxylates, 4H,5H‐pyrano[3,2‐c]chromenes and dihydropyrano[2,3‐c]pyrazoles have been successfully prepared from one‐pot three‐component condensation of aldehyde

  聚吡咯（PPY）/ Fe 3 O 4 / CNT的合成已通过FT-IR，TEM和SEM技术进行了表征，并在几种吡喃衍生物系列的合成中对其催化活性进行了评估。四氢苯并[ b ]吡喃，4H-吡喃-3-羧酸盐，4H，5H-吡喃并[3,2- c ]苯并二氢吡喃并[2,3- c ]吡唑已成功地由一锅三组分缩合反应制得。醛，丙二腈和含活性亚甲基的化合物（二甲酮/乙酰乙酸乙酯/ 4-羟基香豆素/ 3-甲基-2-吡唑啉-5-酮），使用PPY / Fe 3 O 4/ CNT作为一种新的可重复使用的多相催化剂。本方法具有几个优点，例如：产物的高收率，较短的反应时间，容易的后处理步骤以及由于其磁性而易于从反应混合物中分离出催化剂。此外，通过这种方法可以从对苯二甲醛化学选择性合成双苯并[ b ]吡喃。
• Introduction of an efficient DABCO-based bis-dicationic ionic salt catalyst for the synthesis of arylidenemalononitrile, pyran and polyhydroquinoline derivatives
  作者：Mehdi Zabihzadeh、Atefeh Omidi、Farhad Shirini、Hassan Tajik、Mohaddeseh Safarpoor Nikoo Langarudi

  DOI：10.1016/j.molstruc.2020.127730

  日期：2020.4

  Abstract —An affordable DABCO-based bis-dicationic ionic salt ([(DABCO)2C3H5OH]·2Cl) was utilized for the synthesis of arylidenemalononitrile, tetrahydrobenzo[b]pyran, pyrano[2,3-d]-pyrimidinone (thione), dihydropyrano[3,2-c]chromene, and polyhydroquinoline derivatives. The significant features of the presented method are ease of preparation and handling of the catalyst, high catalytic activity, short

  摘要 —一种经济实惠的基于 DABCO 的双阳离子离子盐 ([(DABCO)2C3H5OH]·2Cl) 用于合成亚芳基丙二腈、四氢苯并[b]吡喃、吡喃并[2,3-d]-嘧啶酮（硫酮），二氢吡喃并[3,2-c]色烯和聚氢喹啉衍生物。该方法的显着特点是催化剂易于制备和处理，催化活性高，反应时间短，无需柱色谱分离，后处理程序简单。此外，催化剂可以很容易地回收并在研究的反应中重复使用几个循环。