n-butyl 3-pentafluorophenyl acrylate | 137114-69-3

• 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: n-butyl 3-pentafluorophenyl acrylate
• 英文别名: n-butyl 2,3,4,5,6-pentafluorocinnamate；(E)-butyl 3-(perfluorophenyl)acrylate；butyl 3-(perfluorophenyl)acrylate；(E)-n-butyl 3-(perfluorophenyl)acrylate；Butyl (2E)-3-(2,3,4,5,6-pentafluorophenyl)-2-propenoate；butyl (E)-3-(2,3,4,5,6-pentafluorophenyl)prop-2-enoate
• CAS: 137114-69-3
• 化学式: C₁₃H₁₁F₅O₂
• 分子量: 294.221
• InChiKey: BOIGUMGMKIUORG-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  六氟苯 以 乙醚 为溶剂， 反应 1.75h， 生成 n-butyl 3-pentafluorophenyl acrylate
  参考文献：
  名称：

  A Novel One-Pot Synthesis of Fluorinated α,β-Unsaturated Esters

  摘要：

  The reaction of pentafluorophenylmethylene-triphenylarsorane or p-chloro-tetrafluorophenylmethyl-enetriphenylarsorane, generated in situ from methylene-triphenylarsorane and hexafluorobenzene or chloropenta-fluorobenzene, with bromoacetates giving excellent yields of 3-pentafluorophenyl or 3-p-chloro-tetrafluorophenyl alpha,beta-unsaturated esters with high steroselectivity is described.

  DOI：

  10.1080/00397919108021289

文献信息

• Palladium-Catalyzed Olefination and Arylation of Polyfluoroarenes Using Molecular Oxygen as the Sole Oxidant
  作者：Qiufeng Huang、Xinyu Zhang、Lin Qiu、Jiajun Wu、Hanbing Xiao、Xiaofeng Zhang、Shen Lin

  DOI：10.1002/adsc.201500632

  日期：2015.11.16

  The palladium-catalyzed cross-dehydrogenative-coupling of polyfluoroarenes with alkenes or simple arenes has been developed. The approach is characterized by using atmospheric pressure of molecular oxygen as the sole oxidant, and provides a straightforward and environmentally benign route to functionalized polyfluoroarenes.

  已经开发了钯催化的多氟芳烃与烯烃或简单芳烃的交叉脱氢偶联。该方法的特征在于使用分子氧的大气压作为唯一的氧化剂，并提供了直接且对环境无害的官能化多氟芳烃途径。
• Rh(I)-Catalyzed Olefin Hydroarylation with Electron-Deficient Perfluoroarenes
  作者：Zhong-Ming Sun、Jing Zhang、Rajith S. Manan、Pinjing Zhao

  DOI：10.1021/ja102575d

  日期：2010.5.26

  Assisted by a partially aqueous media, a catalyst system of [Rh(cod)(OH)](2) and DPPBenzene ligand effectively promotes direct conjugate additions by perfluoroarenes. This formal C-H alkylation process represents a rare example of olefin hydroarylation with electron-deficient arenes. The catalyst system can be modified to selectively form the corresponding olefination products under anhydrous conditions.
• Development of a Decarboxylative Palladation Reaction and Its Use in a Heck-type Olefination of Arene Carboxylates
  作者：Andrew G. Myers、Daisuke Tanaka、Michael R. Mannion

  DOI：10.1021/ja027523m

  日期：2002.9.1

  The development of a palladium-catalyzed decarboxylative coupling reaction of arene carboxylates with olefinic substrates is described. The optimized procedure for decarboxylative palladation employs Pd(O2CCF3)2 as catalyst (0.2 equiv) in the presence of Ag2CO3 (3 equiv) in the solvent 5% DMSO-DMF and proceeds at temperatures of 80-120 degrees C with a wide range of arene carboxylates and alkenes as substrates. The process is proposed to proceed by an initial Ar-SE reaction involving ipso attack of an electrophilic Pd(II) intermediate on an arene carboxylate to form an arylpalladium(II) species with loss of carbon dioxide. This intermediate is then proposed to react with an olefinic substrate by steps common to the Heck coupling process. Reoxidation of the liberated Pd(0) in situ is proposed to establish the catalytic cycle.
• Pd-catalyzed aerobic direct olefination of polyfluoroarenes
  作者：Chun-Yang He、Feng-Ling Qing、Xingang Zhang

  DOI：10.1016/j.tetlet.2014.03.096

  日期：2014.4

  The first example of Pd-catalyzed aerobic direct olefination of polyfluoroarenes has been developed. The reaction makes use of molecular O-2 as terminal oxidant, and provides a cost-efficient and environmentally benign access to polyfluoroarene-alkene structures that are of interest in life and material sciences. (C) 2014 Elsevier Ltd. All rights reserved.
• Pd(OAc)₂ Catalyzed Olefination of Highly Electron-Deficient Perfluoroarenes
  作者：Xingang Zhang、Shilu Fan、Chun-Yang He、Xiaolong Wan、Qiao-Qiao Min、Jie Yang、Zhong-Xing Jiang

  DOI：10.1021/ja908434e

  日期：2010.4.7

  An efficient, Pd(OAc)(2) catalyzed method for direct olefination of highly electron-deficient perfluoroarenes was developed. The reaction scope includes a series of activated and nonactivated alkenes in moderate to high yields with moderate to high regio- and stereoselectivities.