(E)-1-(3-phenoxy-1-propen-1-yl)-4-(trifluoromethyl)benzene | 1189373-42-9

• 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)-1-(3-phenoxy-1-propen-1-yl)-4-(trifluoromethyl)benzene
• 英文别名: (E)-4-trifluoromethylcinnamyl phenyl ether；1-[(E)-3-phenoxyprop-1-enyl]-4-(trifluoromethyl)benzene
• CAS: 1189373-42-9
• 化学式: C₁₆H₁₃F₃O
• 分子量: 278.274
• InChiKey: FRUSRBGLKGLOAU-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯酚 在 potassium phosphate 、 dichloro(cycloocta-1,5-diene)palladium (II) 、 四丁基溴化铵 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 28.0h， 生成 (E)-1-(3-phenoxy-1-propen-1-yl)-4-(trifluoromethyl)benzene
  参考文献：
  名称：

  从芳族卤化物，酚和烯丙基氯化物高效钯催化合成肉桂醚

  摘要：

  AbstractA one‐pot, two‐step catalytic protocol for the preparation of cinnamyl ethers from simple and readily available aryl halides, phenols and allyl chloride is reported for the first time. This simple and highly efficient palladium nanoparticles catalytic system shows good regio‐ and stereoselectivities and affords the desired products in good to high yields (49–85%) from aryl iodides. Furthermore, less reactive aryl bromides can also give the cinnamyl ethers in moderate yields (24–72%).magnified image

  DOI：

  10.1002/adsc.201300757

文献信息

• Palladium-catalyzed Mizoroki–Heck reaction of allyl aryl ethers with aryl iodides using phosphine-free hydrazone ligands
  作者：Takashi Mino、Hiroaki Shindo、Tomoko Kaneda、Tomoko Koizumi、Yoshio Kasashima、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/j.tetlet.2009.07.046

  日期：2009.9

  Palladium-catalyzed Mizoroki–Heck reaction of allyl aryl ethers with aryl iodides gave aryl cinnamyl ethers using a catalytic amount of Pd(OAc)2 in DMF at 50 °C with phosphine-free hydrazone as a ligand in good yields.

  钯催化的烯丙基芳基醚与芳基碘化物的Mizoroki-Heck反应在50°C下使用催化量的Pd（OAc）2和无膦作为配体，得到芳基肉桂基醚。
• Homogeneous Pd-Catalyzed Transformation of Terminal Alkenes into Primary Allylic Alcohols and Derivatives
  作者：Ren Tomita、Kohei Mantani、Akiyuki Hamasaki、Tamao Ishida、Makoto Tokunaga

  DOI：10.1002/chem.201403373

  日期：2014.8.4

  Synthesis of primary alcohols from terminal alkenes is an important process in both bulk and fine chemical syntheses. Herein, a homogeneous Pd‐complex‐catalyzed transformation of terminal alkenes into primary allylic alcohols, by using 5 mol % [Pd(PPh3)4] as a catalyst, and H2O, CO2, and quinone derivatives as reagents, is reported. When alcohols were used instead of H2O, allylic ethers were obtained

  从末端烯烃合成伯醇在本体和精细化学合成中都是重要的过程。本文中，通过使用5 mol％[Pd（PPh 3）4 ]作为催化剂，并使用H 2 O，CO 2和醌衍生物作为试剂，将末端烯烃均相的Pd络合物均匀转化为伯烯丙基醇。报告。当使用醇代替H 2 O时，获得了烯丙基醚。拟议的机制包括在π-烯丙基Pd中间体的受阻较弱的末端位置添加氧亲核试剂。
• An Efficient Palladium-Catalyzed Synthesis of Cinnamyl Ethers from Aromatic Halides, Phenols, and Allylic Chloride
  作者：Wei Wang、Rong Zhou、Zhi-Jie Jiang、Kun Wang、Hai-Yan Fu、Xue-Li Zheng、Hua Chen、Rui-Xiang Li

  DOI：10.1002/adsc.201300757

  日期：2014.2.10

  AbstractA one‐pot, two‐step catalytic protocol for the preparation of cinnamyl ethers from simple and readily available aryl halides, phenols and allyl chloride is reported for the first time. This simple and highly efficient palladium nanoparticles catalytic system shows good regio‐ and stereoselectivities and affords the desired products in good to high yields (49–85%) from aryl iodides. Furthermore, less reactive aryl bromides can also give the cinnamyl ethers in moderate yields (24–72%).magnified image