2-羟基乙基(2E)-3-苯基丙-2-烯酸酯 | 17773-43-2

• 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
• 中文名称: 2-羟基乙基(2E)-3-苯基丙-2-烯酸酯
• 英文名称: 2-hydroxyethyl cinnamate
• 英文别名: Zimtsaeure-β-hydroxyaethylester；2-hydroxyethyl 3-phenylprop-2-enoate
• CAS: 17773-43-2
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: WYOVFOGJDRFZBX-UHFFFAOYSA-N

物化性质

• 沸点：
  190-195 °C(Press: 11 Torr)
• 密度：
  1.1558 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2-羟基乙基(2E)-3-苯基丙-2-烯酸酯 、 阿拉酸式苯 在 氯化亚砜 作用下， 以52%的产率得到2-(3-phenylprop-2-enoyloxy)ethyl 1,2,3-benzothiadiazole-7-carboxylate
  参考文献：
  名称：

  Novel Benzo-1,2,3-thiadiazole-7-carboxylate Derivatives As Plant Activators and the Development of Their Agricultural Applications

  摘要：

  Plant activators are a novel kind of agrochemicals that could induce resistance in many plants against a broad spectrum of diseases. To date, only few plant activators have been commercialized. In order to develop novel plant activators, a series of benzo-1,2,3-thiadiazole-7-carboxylate derivatives were synthesized, and the structures were characterized by H-1 NMR, IR, elemental analyses, and HRMS or MS. Their potential systemic acquired resistance as plant activators was evaluated as well. Most of them showed good activity, especially, fluoro-containing compounds 3d and 3e, which displayed excellent SAR-inducing activity against cucumber Erysiphe cichoracearum and Colletotrichum lagenarium in assay screening. Field test results illustrated that compounds 3d and 3e were more potent than the commercial plant activator, S-methyl benzo[1,2,3]thiadiazole-7-carbothioate (BTH) toward these pathogens. Further, the preparation of compound 3d is more facile than BTH with lower cost, which will be helpful for further applications in agricultural plant protection.

  DOI：

  10.1021/jf203974p
• 作为产物：
  描述：

  桂醛乙二缩醛 在 叔丁基过氧化氢 、 potassium carbonate 、 1-(过氧化叔丁基)-1,2-苯碘酰-3(H)-酮 作用下， 以 苯 为溶剂， 反应 8.0h， 以65%的产率得到2-羟基乙基(2E)-3-苯基丙-2-烯酸酯
  参考文献：
  名称：

  环缩醛与高价叔丁基过氧-lambda（3）-碘的氧化环裂解。

  摘要：

  [反应：请参见文本]在室温下，在叔丁基过氧化氢和碳酸钾存在下，在室温下将环缩醛暴露于1-叔丁基过氧-1,2-苯并恶多酚-3（1H）-一会导致氧化环裂解通过中间体叔丁基过氧原酸酯转化为乙二醇单酯。

  DOI：

  10.1021/ol016202x

文献信息

• Rate-Acceleration in Gold-Nanocluster-Catalyzed Aerobic Oxidative Esterification Using 1,2- and 1,3-Diols and Their Derivatives
  作者：Tomohiro Yasukawa、Hiroyuki Miyamura、Shū Kobayashi

  DOI：10.1002/asia.201000624

  日期：2011.2.1

  Aerobic oxidation of aldehydes to 1,2‐ and 1,3‐diol monoesters was catalyzed by polymer‐incarcerated gold nanoclusters under ambient conditions. The esterification proceeded much faster with 1,2‐ and 1,3‐diols and their derivatives rather than with methanol.

  在环境条件下，聚合物包埋的金纳米团簇将醛有氧氧化为1,2和1,3,3-二醇单酯。1,2-和1,3-二醇及其衍生物的酯化反应进行得比甲醇快得多。
• Syntheses of Photosensitive Poly(amino acids)
  作者：Masato Nanasawa、Hiroyoshi Kamogawa

  DOI：10.1246/bcsj.48.2588

  日期：1975.9

  New poly(amino acids) (l-glutamic acid, l-tyrosine and l-lysine) containing photosensitive acryloyl, methacryloyl, and cinnamoyl groups in their side chains were synthesized from the corresponding amino acid NCAs. Their photosensitivities under UV irradiation were also investigated as to kind of functional group and the skeleton portion of the poly(amino acids). As regards the effect of the former, the sensitivities were in the order: acryloyl\simeqmethacryloyl>cinnamoyl; as regards the effect of the latter, the sensitivities were in the order: poly-glutamate>poly-lysine>poly-tyrosine.

  新的含有光敏性丙烯酰、甲基丙烯酰和肉桂酰侧链的多肽（L-谷氨酸、L-酪氨酸和L-赖氨酸）是从相应的氨基酸NCA合成得到的。它们在紫外光照射下的光敏性也根据功能基团和多肽骨架部分进行了研究。就前者的影响而言，敏感性顺序为：丙烯酰≈甲基丙烯酰>肉桂酰；就后者的影响而言，敏感性顺序为：聚谷氨酸>聚赖氨酸>聚酪氨酸。
• Palladium on Carbon-Catalyzed Chemoselective Oxygen Oxidation of Aromatic Acetals
  作者：Naoki Yasukawa、Shota Asai、Maho Kato、Yasunari Monguchi、Hironao Sajiki、Yoshinari Sawama

  DOI：10.1021/acs.orglett.6b02833

  日期：2016.11.4

  unprecedented chemoselective transformation has contributed to forming a novel synthetic process for target molecules. Chemoselective oxidation of aromatic acetals has been accomplished using a reusable palladium on carbon catalyst under atmospheric oxygen conditions to form ester derivatives with tolerance of aliphatic acetals and ketals.

  前所未有的化学选择性转化的发展有助于形成靶分子的新型合成过程。使用可重复使用的钯/碳催化剂在大气氧条件下形成具有脂肪族乙缩醛和缩酮耐受性的酯衍生物，可以实现芳香族乙缩醛的化学选择性氧化。
• Interfacially Cross-Linked Reverse Micelles as Soluble Support for Palladium Nanoparticle Catalysts
  作者：Li-Chen Lee、Yan Zhao

  DOI：10.1002/hlca.201100451

  日期：2012.6

  Reverse micelles (RM) were formed in heptane/CHCl3 with a surfactant carrying the triallylammonium (=triprop‐2‐en‐1‐ylammonium) head group (Scheme). Photo‐cross‐linking with dithiothreitol (=rel‐(2R,3R)‐1,4‐dimercaptobutane‐2,3‐diol; DTT) captured the RMs and afforded organic, soluble nanoparticles in a one‐step reaction. Similar to dendrimers, the cross‐linked reverse micelles could encapsulate palladium

  反向胶束（RM）是在庚烷/ CHCl 3中与表面活性剂带有三烯丙基（= triprop-2-en-1-y）头基形成的（Scheme）。与二硫苏糖醇（= rel-（2 R，3 R）-1,4-二巯基丁烷-2,3-二醇; DTT）的光交联捕获了RM，并在一步反应中获得了有机的可溶性纳米颗粒。与树状聚合物相似，交联的反胶束可以将钯纳米颗粒包裹在其亲水核中，并在催化反应中保护它们。在一系列丙烯酸烷基酯（=丙-2-烯酸烷基酯）和碘代苯的Heck偶联中获得了良好或优异的收率（表1和2）。钯纳米颗粒的催化活性在多次重复运行中得以维持。
• Single step green process for the preparation of substituted cinnamic esters with trans-selectivity
  申请人：Sinha Kumar Arun

  公开号：US20080045742A1

  公开（公告）日：2008-02-21

  The invention provides a green process for direct oxidation of a large number of substituted or unsubstituted cinnamaldehydes or cinnamyl alcohols into the corresponding alkyl or aryl cinnamates in one step. The process of the present invention is a convenient and efficient green process for the preparation of various aryl or alkyl cinnamates under conventional, microwave and ultrasound directly from cinnamaldehydes or cinnamyl alcohols in the presence of an oxidizing agent, catalyst and an alcohol, with or without an organic solvent. These esters are immensely important compounds in flavor, perfumery and pharmaceutical industries. There are several prior arts available for the preparation of cinnamic esters, but all of them suffer from deficiencies such as use of expensive reagents and catalysts, harsh reaction conditions, use of toxic chemicals and others. In contrast, the present methodology is extremely simple and involves reaction of the substrate with an oxidizing agent mixed with a homogeneous or heterogeneous catalyst and an alcohol with or without organic solvent by stirring at room temperature or refluxing or under microwave or ultrasound irradiation to get the requisite products.

  本发明提供了一种绿色工艺，可将大量取代或未取代的肉桂醛或肉桂醇直接氧化成相应的烷基或芳基肉桂酸酯。本发明的工艺是一种方便高效的绿色工艺，可在传统、微波和超声波下从肉桂醛或肉桂醇中直接制备各种芳基或烷基肉桂酸酯，其使用氧化剂、催化剂和醇存在，有机溶剂可有可无。这些酯类化合物在食品香料、香水和制药行业中具有极其重要的作用。有几种先前的方法可用于制备肉桂酸酯，但它们都存在缺陷，例如使用昂贵的试剂和催化剂、严酷的反应条件、使用有毒化学品等等。相比之下，本方法极其简单，只需将底物与氧化剂混合，加入均相或异相催化剂和醇，有机溶剂可有可无，然后在室温或回流或微波或超声波下搅拌反应即可获得所需产品。