(E)-3-(3,4-dimethoxyphenyl)allyl acetate | 31337-58-3

• 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: (E)-3-(3,4-dimethoxyphenyl)allyl acetate
• 英文别名: trans-3,4-Dimethoxycinnamyl acetate；trans-1-Acetoxy-3-<3,4-dimethoxy-phenyl>-prop-2-en, trans-Methyl-coniferylalkohol-acetat；trans-1-Acetoxy-3-(3,4-dimethoxy-phenyl)-prop-2-en, trans-Methyl-coniferylalkohol-acetat；3,4-Dimethoxycinnamyl acetate；[(E)-3-(3,4-dimethoxyphenyl)prop-2-enyl] acetate
• CAS: 31337-58-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: MVLZLHBOBVWBQS-SNAWJCMRSA-N

物化性质

• 沸点：
  361.5±37.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,4-dimethoxyphenyl)allyl acetate 生成 (1RS,2RS)-1-(3,4-dimethoxy-phenyl)-propane-1,2,3-triol
  参考文献：
  名称：

  Adler,E.; Gustafsson,B., Acta Chemica Scandinavica (1947), 1963, vol. 17, p. 27 - 36

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (E)-3-(3,4-dimethoxyphenyl)acrylate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 生成 (E)-3-(3,4-dimethoxyphenyl)allyl acetate
  参考文献：
  名称：

  Acquisition of Female-Attracting Fragrance by Males of Oriental Fruit Fly from a Hawaiian Lei Flower, Fagraea berteriana

  摘要：

  Males of the Oriental fruit fly, Bactrocera dorsalis, are strongly attracted to and compulsively feed on a fragrant lei flower, Fagraea berteriana. A series of phenylpropanoid components, trans-3,4-dimethoxycinnamaldehyde alcohol, its acetate, and trans-3,4-dimethoxycinnamaldehyde were characterized as male attractants The alcohol stimulated the same level of feeding activity as methyl eugenol. Males that fed on flowers selectively converted the attractant components into trans-coniferyl alcohol and stored it in rectal glands. Males scented with the phenylpropanoids were more successful in mating than unfed males, indicating the advantage of acquiring the fragrance in mating success.

  DOI：

  10.1023/b:joec.0000006673.27221.2e

文献信息

• Simple route to substituted tetralones
  作者：Frank Z. Yang、Mary K. Trost、William E. Fristad

  DOI：10.1016/s0040-4039(01)81024-8

  日期：1987.1

  A two step route to highly substituted tetralones via Mn(III) oxidation and cyclization has been demonstrated.

  已经证明了通过Mn（III）氧化和环化形成高度取代的四氢萘酮的两步路线。
• Regioselective Acetoxylation of Terminal Olefins Using a Palladium(II)-Thiadiazole Catalyst
  作者：Xiaohan Li、Bin Sun、Jiadi Zhou、Can Jin、Chuangming Yu

  DOI：10.1002/ejoc.201900128

  日期：2019.4.24

  We have presented the first palladium(II)‐thiadiazole‐ligand catalytic system, employing 1,3,4‐thiadiazole derivative as ligand to achieve the esterification of terminal olefin with excellent regio‐ and stereoselectivity. This work is significant in that it represented the first application of 1,3,4‐thiadiazole in organic synthesis. Furthermore, it was also featured by its satisfied yields, mild reaction

  我们介绍了第一个钯（II）-噻二唑-配体催化体系，采用1,3,4-噻二唑衍生物作为配体，以优异的区域和立体选择性实现末端烯烃的酯化。这项工作意义重大，因为它代表了1,3,4-噻二唑在有机合成中的首次应用。此外，它还具有令人满意的产率，温和的反应条件。
• Allylic C−H Acetoxylation with a 4,5-Diazafluorenone-Ligated Palladium Catalyst: A Ligand-Based Strategy To Achieve Aerobic Catalytic Turnover
  作者：Alison N. Campbell、Paul B. White、Ilia A. Guzei、Shannon S. Stahl

  DOI：10.1021/ja105829t

  日期：2010.11.3

  Pd-catalyzed C-H oxidation reactions often require the use of oxidants other than O(2). Here we demonstrate a ligand-based strategy to replace benzoquinone with O(2) as the stoichiometric oxidant in Pd-catalyzed allylic C-H acetoxylation. Use of 4,5-diazafluorenone (1) as an ancillary ligand for Pd(OAc)(2) enables terminal alkenes to be converted to linear allylic acetoxylation products in good yields

  Pd 催化的 CH 氧化反应通常需要使用 O(2) 以外的氧化剂。在这里，我们展示了一种基于配体的策略，在 Pd 催化的烯丙基 CH 乙酰氧基化中用 O(2) 作为化学计量氧化剂替换苯醌。使用 4,5-二氮杂芴酮 (1) 作为 Pd(OAc)(2) 的辅助配体可使末端烯烃在 1 atm O(2) 下以良好的产率和选择性转化为线性烯丙基乙酰氧基化产物。机理研究表明，1 促进了 π-烯丙基-Pd(II) 中间体的 CO 还原消除，从而消除了这一关键催化步骤中对苯醌的需求。
• Ruthenium-Catalyzed Cross-Metathesis of Allyl Acetate and Styrenes: A Practical Approach to the Synthesis of Tripolinolate A and Its Analogs
  作者：Yasuhiro Araki、Nikola Topolovčan、Martin Kotora

  DOI：10.1002/ejoc.201700132

  日期：2017.4.3

  structurally divergent styrenes were tolerated, and the resultant products were obtained in reasonable yields. The reported method was utilized in the synthesis of inhibitors of the proliferation of glioma and colorectal cancer cells, tripolinolate A and its diacetate analog.

  探索了 Ru 催化的乙酸烯丙酯和苯乙烯交叉复分解的范围。可以容忍各种电子和结构不同的苯乙烯，并以合理的产率获得所得产物。所报道的方法用于合成胶质瘤和结直肠癌细胞增殖抑制剂、三萜醇酯 A 及其二乙酸酯类似物。
• [EN] INSECT TRAP AND METHOD OF USE<br/>[FR] PIÈGE À INSECTES ET PROCÉDÉ D'UTILISATION
  申请人：AGNOVA TECH PTY LTD

  公开号：WO2017015702A1

  公开（公告）日：2017-02-02

  The present invention relates to an apparatus for trapping insects, such as fruit flies, and its use in methods of controlling and/or eradicating insect infestations and monitoring for the presence of insects such as fruit flies. In particular, the apparatus is an insect trap comprising a plurality of members joined at a central region and extending outwardly therefrom to form a structure approximating an open spheroid, the members providing a surface wherein at least 25% of the total surface is coated with an insect trapping adhesive.