Phenyl 4-hydroxycinnamate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Phenyl 4-hydroxycinnamate
• 英文别名: (E)-phenyl 3-(hydroxyphenyl)acrylate；phenyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: XJGDWYSZZPUQSL-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Phenyl 4-hydroxycinnamate 在 聚醚醇 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 sodium;4-[(E)-3-oxo-3-phenoxyprop-1-enyl]phenolate
  参考文献：
  名称：

  Color regulation and stabilization of chromophore by Cys69 in photoactive yellow protein active center

  摘要：

  合成并表征了PYP色素的模型化合物，以研究Cys69残基在活性中心中的作用，该残基与共轭羰基氧和色素硫酯键形成分子内NH⋯OC氢键。模型化合物的UV-vis和13C NMR光谱结果表明，它们使色素的负电荷发生离域，并增强了酚酸阴离子状态中类醌共振结构的贡献。因此，Cys69残基在活性中心中对色彩的调节和色素阴离子的稳定性起着重要作用。

  DOI：

  10.1039/b905835d
• 作为产物：
  描述：

  (E)-phenyl 3-(4-(tert-butyldimethylsilyloxy)phenyl)acrylate 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以84%的产率得到Phenyl 4-hydroxycinnamate
  参考文献：
  名称：

  Color regulation and stabilization of chromophore by Cys69 in photoactive yellow protein active center

  摘要：

  合成并表征了PYP色素的模型化合物，以研究Cys69残基在活性中心中的作用，该残基与共轭羰基氧和色素硫酯键形成分子内NH⋯OC氢键。模型化合物的UV-vis和13C NMR光谱结果表明，它们使色素的负电荷发生离域，并增强了酚酸阴离子状态中类醌共振结构的贡献。因此，Cys69残基在活性中心中对色彩的调节和色素阴离子的稳定性起着重要作用。

  DOI：

  10.1039/b905835d

文献信息

• Synthesis and Antifungal Activity of Cinnamic Acid Esters
  作者：Shinkichi Tawata、Shigehiko Taira、Naotada Kobamoto、Jun Zhu、Masanobu Ishihara、Seizen Toyama

  DOI：10.1271/bbb.60.909

  日期：1996.1

  Cinnamic, p-coumaric and ferulic acids were isolated from pineapple stems (Ananas comosus var. Cayenne). Twenty-four kinds of esters were prepared from these acids, alcohols and the components of Alpinia. Isopropyl 4-hydroxycinnamate (11) and butyl 4-hydroxycinnamate (12) were found to have almost the same effectiveness in antifungal activity against Pythium sp. at 10 ppm as that of the commercial

  从菠萝茎（Ananas comosus var。Cayenne）中分离了肉桂酸，对香豆酸和阿魏酸。由这些酸，醇和高良姜的成分制得二十四种酯。发现4-羟基肉桂酸异丙酯（11）和4-羟基肉桂酸丁酯（12）在对抗腐霉菌属的真菌活性方面具有几乎相同的功效。含量为商业杀菌剂异丙苯酚（kitazin P）的10 ppm。
• COMPOSITION FORMING HEAT-CURED FILM HAVING PHOTO-ALIGNMENT PROPERTIES
  申请人：Nissan Chemical Industries, Ltd.

  公开号：EP2557102A1

  公开（公告）日：2013-02-13

  There is provided a material that exhibits high solvent resistance after the formation of a cured film, excellent photo-alignment capability relative to a polymerizable liquid crystal, satisfactory heat resistance, and high transparency and moreover, that can be dissolved in a glycol-based solvent, a ketone-based solvent, or a lactic acid ester-based solvent that is applicable to the production of an overcoating of a color filter, during the formation of the cured film. A composition for forming thermoset film having photo-alignment properties, comprising: a component (A) that is a compound having a photo-aligning group and a hydroxy group; and a component (B) that is a silicon isocyanate compound. A liquid crystal alignment layer formed from the thermoset film forming composition, and an optical device with a retardation layer obtained by use of the thermoset film forming composition.

  本发明提供了一种材料，该材料在形成固化膜后具有较高的耐溶剂性，与可聚合液晶相比具有优异的光对准能力，耐热性令人满意，透明度高，而且在形成固化膜期间可溶解在乙二醇基溶剂、酮基溶剂或乳酸酯基溶剂中，适用于生产彩色滤光片的外涂层。一种用于形成具有光对准特性的热固性薄膜的组合物，包括：组分（A），即具有光对准基团和羟基的化合物；以及组分（B），即硅异氰酸酯化合物。由该热固性成膜组合物形成的液晶配向层，以及通过使用该热固性成膜组合物而获得的具有延缓层的光学器件。
• CURED FILM FORMATION COMPOSITION, ORIENTATION MATERIAL, AND PHASE DIFFERENCE MATERIAL
  申请人：Nissan Chemical Industries, Ltd.

  公开号：EP2767562A1

  公开（公告）日：2014-08-20

  There is provided a cured-film formation composition that forms a cured film having excellent photoreaction efficiency and solvent resistance, and high adhesion, an orientation material for photo-alignment, and a retardation material formed with the orientation material. The cured-film formation composition comprises a component (A) that is a compound having a photo-aligning group and one substituent selected from a hydroxy group, a carboxy group, and an amino group; a component (B) that is a hydrophilic polymer having one or more substituents selected from a hydroxy group, a carboxy group, and an amino group; and a component (C) that is a cross-linking agent that reacts with the component (A) and the component (B) and reacts at a temperature lower than a sublimation temperature of the component (A), wherein when the component (B) is an acrylic polymer, the cured-film formation composition further comprises a component (E) that is an adhesion enhancing component. The cross-linking agent of the component (C) may be more hydrophilic than the component (A). The orientation material is formed by forming a cured film with the cured-film formation composition and utilizing photo-alignment technique. The retardation material is obtained by applying a polymerizable liquid crystal on the orientation material and curing it.

  本发明提供了一种固化成膜组合物，该组合物可形成具有优异光反应效率和耐溶剂性以及高附着力的固化膜，还提供了一种用于光配位的配向材料，以及一种与配向材料形成的延缓材料。固化成膜组合物包括：组分（A），即具有光配位基团和一个选自羟基、羧基和氨基的取代基的化合物；组分（B），即具有一个或多个选自羟基、羧基和氨基的取代基的亲水性聚合物；和一种成分（C），它是一种交联剂，可与成分（A）和成分（B）反应，反应温度低于成分（A）的升华温度，其中当成分（B）是丙烯酸聚合物时，固化成膜组合物还包括一种成分（E），它是一种附着力增强成分。组分（C）的交联剂可能比组分（A）更亲水。定向材料是通过使用固化成膜组合物形成固化膜并利用光对准技术形成的。将可聚合液晶涂抹在取向材料上并使其固化，即可获得缓凝材料。
• Liquid crystal display device
  申请人：Japan Display Inc.

  公开号：US11036088B2

  公开（公告）日：2021-06-15

  According to one embodiment, a liquid crystal display device includes a first substrate, a second substrate disposed to oppose the first substrate, a layer of liquid crystal located between the first substrate and the second substrate, and an alignment film disposed on the first substrate so as to be in contact with the layer of the liquid crystal. The liquid crystal has a refractive-index anisotropy Δn of 0.11 or more, the layer of the liquid crystal has a thickness d of 2.5 μm or less, and a product Δnd of the refractive-index anisotropy Δn and the thickness d is 0.20 or more but 0.31 or less. The transmissivity of light having a wavelength of 450 nm in the first substrate and the alignment film is 85% or more but 97% or less.

  根据一个实施例，液晶显示装置包括第一基板、与第一基板相对的第二基板、位于第一基板和第二基板之间的液晶层，以及设置在第一基板上以便与液晶层接触的对准膜。液晶的折射率各向异性 Δn 为 0.11 或以上，液晶层的厚度 d 为 2.5 μm 或以下，折射率各向异性 Δn 与厚度 d 的乘积 Δnd 为 0.20 或以上但 0.31 或以下。波长为 450 纳米的光在第一基底和对准膜中的透过率为 85% 或以上，但为 97% 或以下。
• Participation of an Extended p-Oxo Ketene Intermediate in the Dissociative Alkaline Hydrolysis of Aryl 4-Hydroxycinnamates
  作者：Giorgio Cevasco、Sergio Thea

  DOI：10.1021/jo00100a031

  日期：1994.10

  The alkaline hydrolysis of 4-hydroxycinnamate esters of acidic phenols follows an E1cB mechanism and involves the participation of an ''extended'' p-oxo ketene intermediate. The apparent bimolecular rate constant (k(a)K(a)/K-W) for the hydrolysis of the 2,4-dinitrophenyl ester is some 2500-fold larger than that determined from the Hammett relationship for the B(Ac)2 alkaline hydrolysis of substituted 2,4-dinitrophenyl cinnamates. The positive value of the entropy of activation for the hydrolysis of 2,4-dinitrophenyl 4'-hydroxycinnamate and trapping experiments with nitrogen nucleophiles are consistent with the dissociative pathway. A change from a E1cB to a B(Ac)2 mechanism is expected for esters with leaving groups having pK(a) higher than ca. 6.7. The higher E1cB reactivity of 2,4-dinitrophenyl 4'-hydroxycinnamate compared to that of the corresponding 4'-hydroxybenzoate is due to the vinylene group that further favors the dissociative route, probably increasing the stability of the unsaturated intermediate.