trans-2-cinnamyl-4,6-dimethylphenol | 34591-37-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: trans-2-cinnamyl-4,6-dimethylphenol
• 英文别名: 2-Cinnamyl-4,6-dimethylphenol；(E)-2-(3-phenylprop-2-enyl)-4,6-dimethylphenol；2,4-dimethyl-6-[(E)-3-phenylprop-2-enyl]phenol
• CAS: 34591-37-2
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: LEINKDBOYISXIU-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-2-cinnamyl-4,6-dimethylphenol 以 乙腈 为溶剂， 反应 1.0h， 生成 6,8-Dimethyl-flavan
  参考文献：
  名称：

  苯酚-苯乙烯双大分子系统中分子内的激发态相互作用：光化学和光物理研究

  摘要：

  已直接观察到一系列在酚环上带有给电子取代基的反式-2-肉桂基苯酚中苯酚和苯乙烯之间的分子内激发态相互作用，作为乙腈中的激基复合物发射。与模型化合物相比，光化学反应性和相对较低的荧光量子产率是苯酚/苯乙烯相互作用的其他证据。

  DOI：

  10.1016/s0040-4020(01)01132-2
• 作为产物：
  描述：

  (E)-2,4-dimethyl-1-(3-phenylallyloxy)benzene 在 [Au(Cl)PPh₃] 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 41.0h， 以69%的产率得到trans-2-cinnamyl-4,6-dimethylphenol
  参考文献：
  名称：

  金催化的取代烯丙基芳基醚的重排

  摘要：

  三苯基膦金（I）配合物催化芳基烯丙基醚的克莱森型重排成相应的支链和直链产物。产物分布取决于烯丙基醚的烯烃几何形状。立体化学转移实验支持离子机制。

  DOI：

  10.1016/j.tetlet.2010.10.078

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Antimicrobial Properties of Natural Phenols and Related Compounds II: Cinnamylated Phenols and Their Hydrogenation Products
  作者：L. Jurd、K.L. Stevens、A.D. King、K. Mihara

  DOI：10.1002/jps.2600601145

  日期：1971.11

  A variety of nuclear alkylated C-cinnamylphenols were synthesized and tested for antimicrobial activity. These compounds are particularly effective against Gram-positive bacteria.

  合成了多种核烷基化的C-肉桂基酚，并测试了其抗菌活性。这些化合物对革兰氏阳性细菌特别有效。
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
• Intramolecular excited-state interactions in phenol–styrene bicromophoric systems: a photochemical and photophysical study
  作者：M Consuelo Jiménez、Miguel A Miranda、Rosa Tormos

  DOI：10.1016/s0040-4020(01)01132-2

  日期：2002.1

  The intramolecular excited state interaction between phenol and styrene in a series of trans-2-cinnamylphenols bearing electron-donating substituents at the phenolic ring has been directly observed as an exciplex emission in acetonitrile. The photochemical reactivity and the relatively low fluorescence quantum yields as compared with model compounds are additional evidences for the phenol/styrene interaction

  已直接观察到一系列在酚环上带有给电子取代基的反式-2-肉桂基苯酚中苯酚和苯乙烯之间的分子内激发态相互作用，作为乙腈中的激基复合物发射。与模型化合物相比，光化学反应性和相对较低的荧光量子产率是苯酚/苯乙烯相互作用的其他证据。
• Gold-catalyzed rearrangement of substituted allyl aryl ethers
  作者：James R. Vyvyan、Heidi E. Dimmitt、Jennifer K. Griffith、Laura D. Steffens、Rebecca A. Swanson

  DOI：10.1016/j.tetlet.2010.10.078

  日期：2010.12

  Triphenylphosphinegold(I) complexes catalyze the Claisen-type rearrangement of aryl allyl ethers to the corresponding branched and linear products. The product distribution depends on the olefin geometry of the allylic ether. Stereochemical transfer experiments support an ionic mechanism.

  三苯基膦金（I）配合物催化芳基烯丙基醚的克莱森型重排成相应的支链和直链产物。产物分布取决于烯丙基醚的烯烃几何形状。立体化学转移实验支持离子机制。