(E)-3-(2-acetylamino-4-methylphenyl)-propenoic acid butyl ester

• 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: (E)-3-(2-acetylamino-4-methylphenyl)-propenoic acid butyl ester
• 英文别名: (E)-(n)-butyl 3-(2-acetamido-4-methylphenyl)acrylate；(E)-butyl 3-(2-acetamido-4-methylphenyl)acrylate；butyl (E)-3-(2-acetamido-4-methylphenyl)prop-2-enoate
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: WCGXTZHXHPMZDX-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基环己酮 在 过氧化苯甲酸叔丁酯 、 2,2'-硫代二丙烷 、 palladium diacetate 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 24.0h， 生成 (E)-3-(2-acetylamino-4-methylphenyl)-propenoic acid butyl ester
  参考文献：
  名称：

  A Pd-Catalyzed one-pot dehydrogenative aromatization and ortho-functionalization sequence of N-acetyl enamides

  摘要：

  一锅脱氢和邻位官能化序列提供了从易于获得的环状 N-乙酰烯酰胺获得高度官能化的含芳胺衍生物的途径。

  DOI：

  10.1039/c4cc00027g

文献信息

• CC Bond Formation via CH Activation and CN Bond Formation via Oxidative Amination Catalyzed by Palladium- Polyoxometalate Nanomaterials Using Dioxygen as the Terminal Oxidant
  作者：Leng Leng Chng、Jie Zhang、Jinhua Yang、Makhlouf Amoura、Jackie Y. Ying

  DOI：10.1002/adsc.201100362

  日期：2011.11

  An efficient heterogeneous palladium-polyoxometalate catalyst with the formula Pd-H6PV3Mo9O40/C has been successfully developed for carbon-carbon (CC) bond formation via carbon-hydrogen (CH) activation and carbon-nitrogen (CN) bond formation via oxidative amination using oxygen as the terminal oxidant. The coupling processes are simple, and use relatively mild conditions to form the desired products

  已成功开发出一种有效的多相钯-多金属氧酸盐钯-H 6 PV 3 Mo 9 O 40 / C催化剂，用于通过碳-氢（CH）活化和碳-氮（CN）形成碳-碳（CC）键通过使用氧作为末端氧化剂的氧化胺化形成键。偶联过程很简单，并且使用相对温和的条件来形成所需的产物。此外，由于不需要其他试剂（例如有机/无机氧化剂），因此产生的废物更少，并且水是唯一产生的副产物。
• Rh Catalyzed Olefination and Vinylation of Unactivated Acetanilides
  作者：Frederic W. Patureau、Frank Glorius

  DOI：10.1021/ja103834b

  日期：2010.7.28

  In the catalyzed oxidative olefination of acetanilides (oxidative-Heck coupling), Rh offers great advantages over more common Pd catalysts. Lower catalyst loadings, large functional group tolerance (in particular to halides), and higher reactivity of electron-neutral olefins (styrenes) are some of the attractive features. Most interestingly, even ethylene reacts to yield the corresponding acetanilido-styrene

  在乙酰苯胺的催化氧化烯化（氧化-Heck 偶联）中，Rh 比更常见的 Pd 催化剂具有更大的优势。较低的催化剂负载量、较大的官能团耐受性（特别是对卤化物）和电子中性烯烃（苯乙烯）的较高反应性是一些吸引人的特征。最有趣的是，甚至乙烯也会反应生成相应的乙酰苯胺-苯乙烯。此外，Cu(II)氧化剂也可以催化量使用，空气作为末端氧化剂。
• Electrochemical Recycling of Benzoquinone in the Pd/Benzoquinone-Catalyzed Heck-Type Reactions from Arenes
  作者：Christian Amatore、Chama Cammoun、Anny Jutand

  DOI：10.1002/adsc.200600389

  日期：2007.2.5

  Palladium(II) acetate-catalyzed Heck-type reactions have been performed from the arene 1 and alkenes (n-butyl acrylate, styrene) in acetic acid at room temperature, in the presence of a catalytic amount of benzoquinone or hydroquinone. The reactions have been made catalytic in benzoquinone [which is used to continuously oxidize the Pd(0) into to the active Pd(II) species able to activate the ArH bond]

  在催化量的苯醌或对苯二酚存在下，在室温下于乙酸中由芳烃1和烯烃（丙烯酸正丁酯，苯乙烯）进行了乙酸钯（II）催化的Heck型反应。通过在反应中形成的氢醌的电化学氧化，使反应在苯醌中被催化[苯醌被用于将Pd（0）连续氧化为能够激活ArH键的活性Pd（II）物质]苯醌。
• Ruthenium-Catalyzed Oxidative C–H Alkenylations of Anilides and Benzamides in Water
  作者：Lutz Ackermann、Lianhui Wang、Ratnakancana Wolfram、Alexander V. Lygin

  DOI：10.1021/ol203251s

  日期：2012.2.3

  A cationic ruthenium(II) complex enabled efficient oxidative alkenylations of anilides in water as a green solvent and proved applicable to double C-H bond functionalizations of (hetero)aromatic amides with ample scope. Detailed studies provided strong support for a change of ruthenation mechanism in the two transformations, with an irreversible metalation as the key step in cross-dehydrogenative alkenylations of benzamides.
• Selective Pd-Catalyzed Oxidative Coupling of Anilides with Olefins through C−H Bond Activation at Room Temperature
  作者：Maarten D. K. Boele、Gino P. F. van Strijdonck、André H. M. de Vries、Paul C. J. Kamer、Johannes G. de Vries、Piet W. N. M. van Leeuwen

  DOI：10.1021/ja0176907

  日期：2002.2.1

  Using a high-throughput experimentation approach we found a selective and mild Pd-catalyzed oxidative coupling reaction between anilide derivatives and acrylates that occurs through ortho C-H bond activation. The reaction is carried out in an acidic environment and occurs even at room temperature with use of a cheap oxidant (benzoquinone) in yields up to 91%. The benzoquinone possibly also functions as a ligand, stabilizing the catalyst. From the electronic dependence of the reaction and the observed kinetic isotope effect (kH/kD = 3) the key step of the catalytic cycle is believed to be electrophilic attack by a [PdOAc]+ complex on the pi-system of the arene.