3-furfuryl-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine | 1291074-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3-furfuryl-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine
• 英文别名: 3-(Furan-2-ylmethyl)-8-methoxy-2,4-dihydro-1,3-benzoxazine；3-(furan-2-ylmethyl)-8-methoxy-2,4-dihydro-1,3-benzoxazine
• CAS: 1291074-78-6
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: BHLDWZWZWUTVEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-furfuryl-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine 、 以 neat (no solvent, solid phase) 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Innovative approach using aminomaleimide for unlocking phenolic diversity in high-performance maleimidobenzoxazine resins

  摘要：

  A new innovative synthetic approach for the preparation of maleimidobenzoxazines was developed. For the first time the phenolic diversity in maleimidobenzoxazine compounds was enabled, opening many possibilities for tailoring properties of maleimidobenzoxazines through phenolic diversity. The key in a successful implementation of a novel synthetic approach was utilization of aminomaleimide compound prepared by modified synthetic path, without the need for chromatographic purification. Yields of the reaction between aminomaleimide and phenols reached up to 95%, which is a significant improvement prior to previous studies dealing with maleimidobenzoxazines. Aminomaleimide and all novel maleimidobenzoxazine substances were characterized by H-1 NMR, C-13 NMR and FTIR spectroscopies. The curing behaviour of prepared maleimidobenzoxazines was investigated by DSC analysis and mechanical properties by DMA analysis. Novel maleimidobenzoxazines showed similar properties comparing to the already presented in the literature showing high glass transition temperature values over 240 degrees C. Thermogravimetric analysis proved improved thermal stability of maleimidobenzoxazines compared to anilinobenzoxazines. Finally, the use of prepared maleimidobenzoxazines was investigated by the means of Diels-Alder reaction as a possible benzoxazine bearing maleimide group precursor for self-healing purposes. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2017.05.061
• 作为产物：
  描述：

  聚合甲醛 、 2-呋喃甲胺 、 木榴油 以 neat (no solvent) 为溶剂， 反应 1.0h， 以92%的产率得到3-furfuryl-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine
  参考文献：
  名称：

  合成和 共聚 完全基于生物 苯并恶嗪 从 愈创木酚， 糠胺 和硬脂胺

  摘要：

  两个完全基于生物 苯并恶嗪 单体， 3-糠基-8-甲氧基-3,4-二氢-2 H -1,3-苯并恶嗪 （Bzf）和 3-十八烷基-8-甲氧基-3,4-二氢-2 H -1,3-苯并恶嗪（Bzs），已通过无溶剂方法成功合成。其结构已被下列人员确认FTIR光谱， 核磁共振波谱， 和 元素分析。 共聚 的单体已经通过 差示扫描量热法 （数码相机） 测量。结果表明，它们经历了均质共聚当Bzf–Bzs摩尔比超过1 ：2时，发现Bzf的呋喃部分对共聚具有有益作用，包括对固化过程的促进作用，交联密度的改善和热性能的增强共聚树脂。基于机制开环聚合 的 苯并恶嗪，这些作用可能归因于呋喃环结构的亲电子芳族取代。这些发现对设计具有理想性能的完全基于生物的新型聚苯并恶嗪具有重要意义。

  DOI：

  10.1039/c2gc35796h

文献信息

• Preparation and characterization of fully renewable polybenzoxazines from monomers containing multi-oxazine rings
  作者：Lei Zhang、Yejun Zhu、Dan Li、Min Wang、Haibin Chen、Jingshen Wu

  DOI：10.1039/c5ra17164d

  日期：——

  Two fully renewable benzoxazine monomers containing multi-oxazine rings were synthesized and used to prepare polybenzoxazines. The structures of the monomers, prepared from renewable feedstock (vanillin, guaiacol, octadecylamine and furfurylamine) were supported by FT-IR and NMR spectral analyses. The melting points and curing temperatures were characterized through DSC. Thermal initiated ring-opening

  合成了两个含有多恶嗪环的完全可再生的苯并恶嗪单体，并用于制备聚苯并恶嗪。由可再生原料（香兰素，愈创木酚，十八烷基胺和糠胺）制备的单体结构通过FT-IR和NMR光谱分析得到支持。熔点和固化温度通过DSC表征。通过FT-IR监测单体的热引发的开环聚合。检查了聚苯并恶嗪的溶解度，并弄清了由具有单恶嗪和多恶嗪环的单体制备的聚合物之间的交联差异。通过能量计算，发现取代优选发生在呋喃环上。通过TGA对热性能进行了研究，结果显示出良好的热稳定性（T在284°C和335°C下为d5％）和较高的炭收率（高达59.6％）。机械性能通过DMA表征，它显示了155°C的玻璃化转变温度。由于结构的特殊性，聚苯并恶嗪还显示出pH响应性，并且可以在不同条件下可逆地改变颜色。
• Synthesis and thermal properties of a bio-based polybenzoxazine with curing promoter
  作者：CaiFei Wang、ChunHua Zhao、JiaQin Sun、SanQing Huang、XiangDong Liu、Takeshi Endo

  DOI：10.1002/pola.26587

  日期：2013.5.1

  in the presence of methyl p‐toluenesulfonate (PTSM) has been studied by FTIR and DSC, and the thermal stability of the cured resin has been evaluated by thermogravimetric analysis. It was found that PTSM is a good promoter that serves to avoid thermal decomposition of the bio‐based monomer during the curing process at high temperature. In contrast to the situation with neat Bzf, the presence of PTSM

  已使用愈创木酚，糠胺和多聚甲醛为原料制备了完全生物基的苯并恶嗪，3-糠基-8-甲氧基-3,4-二氢-2H-1,3-苯并恶嗪（Bzf）。其化学结构已通过1H和13C NMR，FTIR和元素分析进行​​了表征。通过FTIR和DSC研究了在对甲苯磺酸甲酯（PTSM）存在下Bzf的聚合行为，并通过热重分析评估了固化树脂的热稳定性。发现PTSM是一种良好的促进剂，可避免高温固化过程中生物基单体的热分解。与纯Bzf的情况相比，PTSM的存在（Bzf为5 mol％）显着改善了聚合行为，包括将聚合温度从240降低到174°C，将在200°C加热时达到凝胶点所需的时间从47分钟缩短至20分钟，并且将固化树脂的炭收率从53％提高至62％。此外，这些观察到的有关PTSM促进作用的实验结果是根据几种可能的机理解释的，这些机理涉及对C分解的催化作用。 O键在配位开环反应和从苯氧基结构的酚结构重排两者。©2013 Wiley
• Microwave-assisted solvent-free synthesis of novel benzoxazines: A faster and environmentally friendly route to the development of bio-based thermosetting resins
  作者：Jéssica R. Oliveira、Lloyd R. V. Kotzebue、Francisco W. M. Ribeiro、Beatriz C. Mota、Dávila Zampieri、Selma E. Mazzetto、Hatsuo Ishida、Diego Lomonaco

  DOI：10.1002/pola.28755

  日期：2017.11.1

  amines are successfully fused into guaiacol‐derived 3,4‐dihydro‐2H‐1,3‐benzoxazines. The reactions conducted under microwave irradiation are completed much faster than those under traditional heating, reducing the reaction time from hours to only 6 min, with good yields. The chemical structures of novel benzoxazines are confirmed by 1H and 13C NMR spectroscopy, FTIR, and HR‐MS. The thermal behavior

  微波辅助有机合成（MAOS）是一种完善的技术，已用于增强化学反应。在此，探讨了MAOS的多功能性，描述了在无溶剂条件下向新型生物基苯并恶嗪生产的环境友好型一锅法。木质素衍生物愈创木酚，多聚甲醛以及不同的共轭和非共轭胺已成功融合到由愈创木酚衍生的3,4-二氢-2 H -1,3-苯并恶嗪中。在微波辐射下进行的反应比在传统加热下完成的反应快得多，反应时间从数小时减少到只有6分钟，并且收率很高。1 H和13证实了新型苯并恶嗪的化学结构C NMR光谱，FTIR和HR-MS。通过差示扫描量热法（DSC）和热重分析（TGA）对树脂的热行为进行了评估，结果表明这些聚合物具有良好的热稳定性和宽广的加工范围，聚合起始温度高于230°C。这些结果表明，与传统的生产此类树脂的方法相比，已有显着改进，而传统方法通常是通过耗时的程序并在有毒溶剂的存在下获得的。因此，MAOS被认为是合成生态友好型苯并恶嗪的绿色高效策略。©2017
• Synthesis and copolymerization of fully bio-based benzoxazines from guaiacol, furfurylamine and stearylamine
  作者：CaiFei Wang、JiaQin Sun、XiangDong Liu、Atsushi Sudo、Takeshi Endo

  DOI：10.1039/c2gc35796h

  日期：——

  Two fully bio-based benzoxazine monomers, 3-furfuryl-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine (Bzf) and 3-octadecyl-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine (Bzs), have been successfully synthesized via a solventless method. Their structures have been confirmed by FTIR spectroscopy, NMR spectroscopy, and elemental analysis. Copolymerization of the monomers has been investigated by differential scanning

  两个完全基于生物 苯并恶嗪 单体， 3-糠基-8-甲氧基-3,4-二氢-2 H -1,3-苯并恶嗪 （Bzf）和 3-十八烷基-8-甲氧基-3,4-二氢-2 H -1,3-苯并恶嗪（Bzs），已通过无溶剂方法成功合成。其结构已被下列人员确认FTIR光谱， 核磁共振波谱， 和 元素分析。 共聚 的单体已经通过 差示扫描量热法 （数码相机） 测量。结果表明，它们经历了均质共聚当Bzf–Bzs摩尔比超过1 ：2时，发现Bzf的呋喃部分对共聚具有有益作用，包括对固化过程的促进作用，交联密度的改善和热性能的增强共聚树脂。基于机制开环聚合 的 苯并恶嗪，这些作用可能归因于呋喃环结构的亲电子芳族取代。这些发现对设计具有理想性能的完全基于生物的新型聚苯并恶嗪具有重要意义。
• Innovative approach using aminomaleimide for unlocking phenolic diversity in high-performance maleimidobenzoxazine resins
  作者：Žiga Štirn、Aleš Ručigaj、Matjaž Krajnc

  DOI：10.1016/j.polymer.2017.05.061

  日期：2017.6

  A new innovative synthetic approach for the preparation of maleimidobenzoxazines was developed. For the first time the phenolic diversity in maleimidobenzoxazine compounds was enabled, opening many possibilities for tailoring properties of maleimidobenzoxazines through phenolic diversity. The key in a successful implementation of a novel synthetic approach was utilization of aminomaleimide compound prepared by modified synthetic path, without the need for chromatographic purification. Yields of the reaction between aminomaleimide and phenols reached up to 95%, which is a significant improvement prior to previous studies dealing with maleimidobenzoxazines. Aminomaleimide and all novel maleimidobenzoxazine substances were characterized by H-1 NMR, C-13 NMR and FTIR spectroscopies. The curing behaviour of prepared maleimidobenzoxazines was investigated by DSC analysis and mechanical properties by DMA analysis. Novel maleimidobenzoxazines showed similar properties comparing to the already presented in the literature showing high glass transition temperature values over 240 degrees C. Thermogravimetric analysis proved improved thermal stability of maleimidobenzoxazines compared to anilinobenzoxazines. Finally, the use of prepared maleimidobenzoxazines was investigated by the means of Diels-Alder reaction as a possible benzoxazine bearing maleimide group precursor for self-healing purposes. (C) 2017 Elsevier Ltd. All rights reserved.