acenaphtho[1,2-b]pyrido[2,3-e]pyrazine | 821773-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: acenaphtho[1,2-b]pyrido[2,3-e]pyrazine
• 英文别名: 3,5,10-triazapentacyclo[10.7.1.02,11.04,9.016,20]icosa-1(19),2,4(9),5,7,10,12,14,16(20),17-decaene
• CAS: 821773-03-9
• 化学式: C₁₇H₉N₃
• 分子量: 255.279
• InChiKey: SGPYOVPUEDLNAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  五羰基溴铼(I) 、 acenaphtho[1,2-b]pyrido[2,3-e]pyrazine 以 甲苯 为溶剂， 以71%的产率得到fac-[Re(CO)3Br(NC5H3(NC(C10H6)CN))]
  参考文献：
  名称：

  The Re(I) coordination chemistry of a series of pyrido[2,3-b]pyrazine-derived ligands: Syntheses, characterisation and crystal structures

  摘要：

  Reaction of 2,3-diaminopyridine with one equivalent of a functionalised vicinal diketone, in ethanol, yields a series of ligands based upon the pyrido[2,3-b]pyrazine core. The ligands were characterised by (1)H, (13)C-{(1)H} NMR, MS and UV-Vis spectroscopy. Reaction of the ligands with one equivalent of (ReBr(CO)(5)) gave a series of Re-L(n) complexes based upon the general formula fac-[ReBr(CO)(3)(L)] (where L = pyrido[2,3-b]pyrazine-derived ligands, L(1)-L(6)). Solution IR studies confirmed the retention of the facially capped, tri-carbonyl coordination geometry at rhenium, and (1)H NMR studies confirmed coordination of the ligand to Re(I). El HR MS data were obtained for each complex confirming the proposed formulation and stoichiometry. Single crystal X-ray structures were obtained for three of the complexes (Re-L(1), Re-L(2), Re-L(6)), with each demonstrating that the ligands coordinate to Re([) in a bidentate manner, via a four-membered chelate ring, which was unsymmetrical in the former two cases. The electronic absorption spectra of the complexes showed absorption into the visible region ca. 375-500 nm, (the complexes are orange-red in appearance). Following irradiation at 350-450 nm, the complexes display a solid-state broad emission peaking between 600-700 nm. The complexes were not sufficiently luminescent in solution to allow further investigation into the origin of this emission band, although with reference to related 1,8-naphthyridine complexes of Re(I) it is likely to incorporate significant (3)MLCT character. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.11.013
• 作为产物：
  描述：

  2,3-二氨基吡啶 、 苊醌 在 zirconium oxide salicylaldehyde-(3-aminopropyl)trimethoxysilane imine complex modified SBA-15 作用下， 以 水 为溶剂， 反应 2.0h， 以99%的产率得到acenaphtho[1,2-b]pyrido[2,3-e]pyrazine
  参考文献：
  名称：

  锆席夫碱络合物改性介孔二氧化硅作为合成含氮吡嗪杂环的有效催化剂

  摘要：

  合成了锆席夫碱配合物改性的 SBA-15，并通过粉末 X 射线衍射 (XRD)、BET 氮吸附-解吸方法、红外光谱和热重分析进行了表征。XRD 和 BET 分析表明 SBA-15 的结构特性在接枝过程中得以保留。改性的 SBA 作为多相催化剂成功应用于合成含氮吡嗪基杂环库，在水介质中以良好的收率。图文摘要锆席夫碱配合物改性介孔二氧化硅作为合成含氮杂环的有效催化剂吡嗪基杂环

  DOI：

  10.1007/s10562-013-0999-1

文献信息

• Organocatalytic Combinatorial Synthesis of Quinazoline, Quinoxaline and Bis(indolyl)methanes
  作者：Fatemeh Malamiri、Samad Khaksar、Rashid Badri、Elham Tahanpesar

  DOI：10.2174/1386207323666191213123026

  日期：2020.3.16

  bis(indolyl)methanes was developed using 3,5-bis(trifluoromethyl) phenyl ammonium hexafluorophosphate (BFPHP) as a novel organocatalyst. MATERIALS AND METHODS All of the obtained products are known compounds and identified by IR, 1HNMR, 13CNMR and melting points. RESULT Various products were obtained in good to excellent yields under reaction conditions. CONCLUSION The BFPHP organocatalyst demonstrates a novel class

  目的和目的使用3,5-双（三氟甲基）苯基六氟磷酸铵（BFPHP）作为新型有机催化剂，开发了一种高效且实用的合成杂环化合物的方法，例如喹唑啉，喹喔啉和双（吲哚基）甲烷。材料与方法所有获得的产物均为已知化合物，通过IR，1HNMR，13CNMR和熔点鉴定。结果在反应条件下获得了各种产品，收率良好至优异。结论BFPHP有机催化剂显示出一类新型的不对称有机催化剂，在绿色化学中引起了广泛的关注。
• A general and inexpensive protocol for the nanomagnetic 5-sulfosalicylic acid catalyzed the synthesis of tetrahydrobenzo[b]pyrans and quinoxaline derivatives
  作者：Farzaneh Saboury、Najmedin Azizi、Zohreh Mirjafari、Mohammad Mahmoudi Hashemi

  DOI：10.1007/s13738-020-01948-5

  日期：2020.10

  Fe3O4@SiO2@5-SA (20 mg) showed excellent reactivity for greener synthesis of tetrahydrobenzo[b]pyrans via a three-component reaction of different aromatic aldehydes, malononitrile and dimedone in good to excellent yields (70–95%) in pure water at short reaction times (40–150 min). The method shows eco-friendly synthesis of quinoxaline derivatives from direct condensation of substituted 1,2-diamine with various

  在这项研究中，通过将水溶性5-磺基水杨酸锚定在表面二氧化硅改性的Fe 3 O 4上，制备了具有高负载多功能酸性基团的新型酸官能化磁性纳米粒子。磁性可循环利用的Fe 3 O 4 @SiO 2@ 5-SA（20毫克）显示出不同的芳香性醛，丙二腈和二甲酮的三组分反应，可在较短的时间里纯净水中获得良好至优异的收率（70-95％），从而对绿色四氢苯并[b]吡喃的合成具有优异的反应性。反应时间（40–150分钟）。该方法表明，在室温下，乙醇中的取代的1,2-二胺与各种1,2-二羰基直接缩合，可以生态友好地合成喹喔啉衍生物，从而在较短的时间内即可获得所需的喹喔啉，并具有良好或优异的收率（60-97％）反应时间（120–240分钟）。用扫描电子显微镜，X射线粉末衍射，傅立叶平移红外光谱，振动样品磁强计和热重分析法研究了MNP的形态和磁性。结果表明，Fe 3 O4 @SiO 2 @ 5-SA催化剂可通过外部
• An Efficient and Green Procedure for the Synthesis of Quinoxaline Derivatives using 3,5-Bis(trifluoromethyl)phenylammonium triflate (BFPAT) Organocatalyst
  作者：Mandana Alipour、Zinatossadat Hossaini、Samad Khaksar、Faramarz Rostami-Charati

  DOI：10.2174/1570178617666200313105049

  日期：2021.3

  The application of 3,5-bis(trifluoromethyl)phenylammonium triflate (BFPAT) as a convenient new organocatalyst for the synthesis of quinoxaline derivatives is described. In the presence of BFPAT, one-pot synthesis of a wide variety of quinoxaline derivatives was achieved by the reaction of various o-phenylenediamines and 1,2-dicarbonyl compounds in water.

  描述了3,5-双（三氟甲基）苯基三氟甲磺酸铵（BFPAT）作为合成喹喔啉衍生物的便捷新型有机催化剂的应用。在BFPAT的存在下，通过各种邻苯二胺和1,2-二羰基化合物在水中的反应，可以实现一锅合成多种喹喔啉衍生物。
• A Novel One-Pot Synthesis of Quinoxaline Derivatives in Fluorinated Alcohols
  作者：Samad Khaksar、Fariba Rostamnezhad

  DOI：10.5012/bkcs.2012.33.8.2581

  日期：2012.8.20

  Hexafluoroisopropanol (HFIP) is explored as an effective medium for the synthesis of quinoxaline derivatives in high yields at room temperature. The solvent (HFIP) can be readily separated from reaction products and recovered in excellent purity for direct reuse.

  六氟异丙醇 (HFIP) 被探索为在室温下以高产率合成喹喔啉衍生物的有效介质。溶剂 (HFIP) 可以很容易地从反应产物中分离出来，并以极好的纯度回收以供直接重复使用。
• Pentafluorophenylammonium triflate: A highly efficient catalyst for the synthesis of quinoxaline derivatives in water
  作者：Samad Khaksar、Hanieh Radpeyma

  DOI：10.1016/j.crci.2013.11.009

  日期：2014.10

  Résumé A simple, inexpensive, environmentally friendly and efficient route for the rapid and efficient synthesis of quinoxaline derivatives using pentafluorophenylammonium triflate (PFPAT) as a catalyst is described. Various quinoxaline derivatives were synthesized in good to excellent yields. The preparation of PFPAT catalyst from simple and readily available starting materials makes this method more affordable.

  摘要 描述了一种简单、廉价、环保且高效的方法，通过使用五氟苯基铵三氟甲磺酸盐（PFPAT）作为催化剂，快速高效地合成喹啉衍生物。合成了多种喹啉衍生物，产率良好至优异。使用简单且易得的原材料制备PFPAT催化剂使得此方法更加经济实惠。