allyl 3,4,5-tris(allyloxy)benzoate | 1407185-08-3

• 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: allyl 3,4,5-tris(allyloxy)benzoate
• 英文别名: Prop-2-enyl 3,4,5-tris(prop-2-enoxy)benzoate；prop-2-enyl 3,4,5-tris(prop-2-enoxy)benzoate
• CAS: 1407185-08-3
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: CXISMDRPGTXGQV-UHFFFAOYSA-N

物化性质

• 沸点：
  390.7±42.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 3,4,5-tris(allyloxy)benzoate 在 3-tert-butyl-4-hydroxy-5-methylbenzenethiol 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 54.0h， 以80%的产率得到3,4,5-triglycidylether glycidyl benzoate
  参考文献：
  名称：

  How a bio-based epoxy monomer enhanced the properties of diglycidyl ether of bisphenol A (DGEBA)/graphene composites

  摘要：

  由可再生没食子酸合成了生物基环氧单体（GA-II）。所含的芳香族基团使其能够通过强π-π相互作用被吸收到石墨烯表面，拉曼光谱和紫外光谱证明了这一点。 GA-II锚定石墨烯很容易均匀分散在环氧树脂中。固化后，石墨烯/环氧树脂复合材料表现出良好的机械性能、优异的导热性以及高导电性等优异性能。仅添加2 wt%的GA-II/石墨烯，复合材料的拉伸强度、拉伸模量、弯曲强度和弯曲模量分别提高了27%、47%、9%和21%。热导率和电导率也分别提高了 12 倍（从 0.15 到 1.8 W m−1 K−1）和 8 个数量级（从 7.0 × 10−15 到 3.28 × 10−5 s cm−1）。这项工作为我们提供了一种高效的环保石墨烯分散剂，并展示了一种制备具有优异性能的环氧/石墨烯复合材料的有效方法。

  DOI：

  10.1039/c3ta01700a
• 作为产物：
  描述：

  没食子酸 、 3-溴丙烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.58h， 以84%的产率得到allyl 3,4,5-tris(allyloxy)benzoate
  参考文献：
  名称：

  Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers

  摘要：

  研究了使用南极酵母的脂肪酶B和水合过氧化氢在辛酸存在下对烯丙基没食子酸和香草酸进行化学酶促环氧化的过程。每个烯丙双键使用1摩尔当量的辛酸和1.8–2摩尔当量的H2O2可以得到较高的环氧化转化率（烯丙基没食子酸的产率为89%，烯丙基香草酸的产率为87%），与有害的过酸mCPBA相比（每个双键使用1.5–3.2摩尔当量可得到75–85%的产率）。所获得的环氧化产物可用于新型生物基环氧树脂的配方中。

  DOI：

  10.1039/c2gc35558b

文献信息

• Thiol–Ene Elastomers Derived from Biobased Phenolic Acids with Varying Functionality
  作者：Guozhen Yang、Samantha L. Kristufek、Lauren A. Link、Karen L. Wooley、Megan L. Robertson

  DOI：10.1021/acs.macromol.6b01018

  日期：2016.10.25

  thiol functional groups). The networks derived from the higher functionality allylated phenolic acids also exhibited lower elongation at break and associated tensile strength and tensile toughness, likely due to increased heterogeneity of the networks (indicated by higher glass transition widths compared to the networks derived from difunctional allylated phenolic acids). All networks exhibited behavior

  探索了基于植物酚酸的硫醇烯弹性体的合成和物理性能。使官能度不同的酚酸（每个分子具有2至4个羟基和羧基）和官能团的相对位置（邻位，间位，对位）烯丙基化，然后使用光引发剂与多官能硫醇反应。表征了所得弹性体的热和机械行为。衍生自双官能烯丙基化酚酸的网络显示出窄的玻璃化转变温度（表明高度的网络均匀性）和与它们的交联密度相关的玻璃化转变温度（T g）。该段烯丙基在烯丙基化酚酸上的位置产生了具有最高交联密度，T g，模量，拉伸强度和断裂伸长率的网络（其次是邻位，然后是间位）。随着烯丙基化单体的官能度增加（每个分子增加至3-4个烯丙基），交联密度仍然很高，而T g减少，归因于整个网络结构中较低的苯环浓度（因为所有网络均以烯丙基和硫醇官能团的化学计量比制备）。衍生自较高官能度的烯丙基酚酸的网络还表现出较低的断裂伸长率和相关的拉伸强度和拉伸韧性，这可能是由于网络的不均一性增加（与衍生自双官能烯丙基化酚酸的网络相比，玻璃化转变宽度较高所表明）
• Synthesis of multifunctional monomers for patterning pixel define layer of organic light emitting diode
  作者：Sung Hoon Park、Genggongwo Shi、Duck Min Seo、Minji Kim、Jeseob Kim、Lee Soon Park

  DOI：10.1080/15421406.2018.1470710

  日期：2018.3.4

  Organic light emitting diode (OLED) is widely used as displays for small devices like cellular phone, tablet and wearable devices as well as large devices like TV. Photolithography utilizing black negative-tone photoresist is the vital process for patterning the black pixel define layer (PDL). In this work we report the syntheses of thermally-stable multifunctional monomers and evaluation of their contribution to the patterning of black PDL in OLED panel.
• [EN] POLYTHIOL COMPOUNDS AND PROCESS FOR PREPARATION THEREOF<br/>[FR] COMPOSÉS POLYTHIOL ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：[en]HENKEL AG & CO. KGAA

  公开号：WO2023110270A1

  公开（公告）日：2023-06-22

  The present application is directed to a polythiol compound obtainable independently from a) eugenol, b) gallic acid, c) the adduct of guaiacol and vanillin or d) resveratrol and, respectively, having the general Formula VIA, VIB, VIC or VID, wherein: R1is a C1-C18alkylene group, C2-C18oxyalkylene group, C2-C18thioalkylene group, C6-C18arylene or C7-C18aralkylene group; and R2is H or methyl.
• Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers
  作者：Chahinez Aouf、Jérôme Lecomte、Pierre Villeneuve、Eric Dubreucq、Hélène Fulcrand

  DOI：10.1039/c2gc35558b

  日期：——

  The chemo-enzymatic epoxidation of allylated gallic and vanillic acids with lipase B from Candida antarctica and aqueous hydrogen peroxide in the presence of caprylic acid was investigated. The use of 1 molar eq of caprylic acid and 1.8–2 molar eq of H2O2 per allylic double bond led to a high degree of conversion to epoxides (89% yield for allylated gallic acid and 87% yield for allylated vanillic acid) comparatively to the hazardous peracid mCPBA (1.5–3.2 molar eq per double bond allowed 75–85% yield). The epoxidized products obtained could be used in the formulation of novel bio-based epoxy resins.

  研究了使用南极酵母的脂肪酶B和水合过氧化氢在辛酸存在下对烯丙基没食子酸和香草酸进行化学酶促环氧化的过程。每个烯丙双键使用1摩尔当量的辛酸和1.8–2摩尔当量的H2O2可以得到较高的环氧化转化率（烯丙基没食子酸的产率为89%，烯丙基香草酸的产率为87%），与有害的过酸mCPBA相比（每个双键使用1.5–3.2摩尔当量可得到75–85%的产率）。所获得的环氧化产物可用于新型生物基环氧树脂的配方中。
• How a bio-based epoxy monomer enhanced the properties of diglycidyl ether of bisphenol A (DGEBA)/graphene composites
  作者：Lijun Cao、Xiaoqing Liu、Haining Na、Yonggang Wu、Wenge Zheng、Jin Zhu

  DOI：10.1039/c3ta01700a

  日期：——

  A bio-based epoxy monomer (GA-II) was synthesized from renewable gallic acid. The aromatic group contained made it capable of being absorbed onto the surface of graphene via strong π–π interactions, which was proven by Raman spectra and UV spectra. The GA-II anchored graphene was easily homogeneously dispersed in the epoxy resin. After solidification, the graphene/epoxy composites demonstrated superior performances in terms of good mechanical properties, excellent thermal conductivity, as well as high electrical conductivity. With the addition of only 2 wt% GA-II/graphene, the tensile strength, tensile modulus, flexural strength and flexural modulus of the composites were improved by 27%, 47%, 9% and 21%, respectively. The thermal and electrical conductivities were also improved by 12-fold (from 0.15 to 1.8 W m−1 K−1) and 8 orders (from 7.0 × 10−15 to 3.28 × 10−5 s cm−1), respectively. This work provided us with an environmentally friendly agent with high efficiency for graphene dispersion and demonstrated an efficient method for fabricating epoxy/graphene composites with superior properties.

  由可再生没食子酸合成了生物基环氧单体（GA-II）。所含的芳香族基团使其能够通过强π-π相互作用被吸收到石墨烯表面，拉曼光谱和紫外光谱证明了这一点。 GA-II锚定石墨烯很容易均匀分散在环氧树脂中。固化后，石墨烯/环氧树脂复合材料表现出良好的机械性能、优异的导热性以及高导电性等优异性能。仅添加2 wt%的GA-II/石墨烯，复合材料的拉伸强度、拉伸模量、弯曲强度和弯曲模量分别提高了27%、47%、9%和21%。热导率和电导率也分别提高了 12 倍（从 0.15 到 1.8 W m−1 K−1）和 8 个数量级（从 7.0 × 10−15 到 3.28 × 10−5 s cm−1）。这项工作为我们提供了一种高效的环保石墨烯分散剂，并展示了一种制备具有优异性能的环氧/石墨烯复合材料的有效方法。