Zimtsaeure-2-methoxyethylester | 3488-02-6

• 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: Zimtsaeure-2-methoxyethylester
• 英文别名: cinnamic acid 2-methoxyethyl ester；2-Methoxyethyl cinnamate；2-methoxyethyl 3-phenylprop-2-enoate
• CAS: 3488-02-6
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: NKRHGHSAIFTFDL-UHFFFAOYSA-N

物化性质

• 熔点：
  304-306 °C
• 沸点：
  311.1±17.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙二醇甲醚 、 肉桂醇 在 manganese(IV) oxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4-甲氧基-3-硝基三氟甲苯 作用下， 以 甲苯 为溶剂， 以82%的产率得到Zimtsaeure-2-methoxyethylester
  参考文献：
  名称：

  N-Heterocyclic carbene-catalyzed oxidations

  摘要：

  N-Hererocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized,, protected carboxylates. The oxidation proceeds Under mild conditions, with low loadings of including a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.

  DOI：

  10.1016/j.tet.2008.10.033

文献信息

• 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。
• Nucleophilic Iron Catalysis in Transesterifications: Scope and Limitations
  作者：Silja Magens、Bernd Plietker

  DOI：10.1021/jo1004636

  日期：2010.6.4

  The ester bond is one of the most common structural motifs found in nature. Apart from the condensation between an acid and an alcohol, transesterifications represent another mechanistic alternative for the preparation of this compound class. The present paper summarizes our most recent investigations in this field, using nucleophilic iron complexes as catalysts for transesterifications under neutral conditions. This new type of metal catalyst complements the existing methodologies, which rely on Lewis acidic metal complexes. Investigations on scope and limitations, stereochemical course, and chemoselectivities will be presented.
• N-Heterocyclic carbene-catalyzed oxidations
  作者：Brooks E. Maki、Audrey Chan、Eric M. Phillips、Karl A. Scheidt

  DOI：10.1016/j.tet.2008.10.033

  日期：2009.4

  N-Hererocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized,, protected carboxylates. The oxidation proceeds Under mild conditions, with low loadings of including a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.