butyl (E)-3-(2-methylnaphthalen-1-yl) acrylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: butyl (E)-3-(2-methylnaphthalen-1-yl) acrylate
• 英文别名: butyl (E)-3-(2-methylnaphthalen-1-yl)prop-2-enoate
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: AXAXMJKUKIDAAK-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 1-溴-2-甲基萘 在 bis(η3-allyl-μ-chloropalladium(II)) 、 顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以92%的产率得到butyl (E)-3-(2-methylnaphthalen-1-yl) acrylate
  参考文献：
  名称：

  Palladium/Tetraphosphine Catalysed Heck Reaction with ortho-Substituted Aryl Bromides

  摘要：

  四膦化合物 cis,cis,cis-1,2,3,4-四（二苯基膦甲基）环戊烷与 [PdCl(C3H5)]2 结合，催化了丁基丙烯酸酯与多种空间位阻较大的芳基溴化物的 Heck 反应，产物收率很高。使用 ortho-取代芳基溴化物时，循环次数高达 630-89 000，而在此催化剂存在下，使用二-ortho-取代芳基溴化物时循环次数为 43-2600。

  DOI：

  10.1055/s-2001-18752

文献信息

• Palladium/Tetraphosphine Catalysed Heck Reaction with ortho-Substituted Aryl Bromides
  作者：Marie Feuerstein、Henri Doucet、Maurice Santelli

  DOI：10.1055/s-2001-18752

  日期：——

  The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane associated to [PdCl(C3H5)]2 catalyses the Heck reaction of butyl acrylate with a wide range of sterically demanding aryl bromides, furnishing the addition product in high yields. Turnover numbers as high as 630-89 000 have been obtained using ortho-substituted aryl bromides and 43-2600 with di-ortho-substituted aryl bromides in the presence of this catalyst.

  四膦化合物 cis,cis,cis-1,2,3,4-四（二苯基膦甲基）环戊烷与 [PdCl(C3H5)]2 结合，催化了丁基丙烯酸酯与多种空间位阻较大的芳基溴化物的 Heck 反应，产物收率很高。使用 ortho-取代芳基溴化物时，循环次数高达 630-89 000，而在此催化剂存在下，使用二-ortho-取代芳基溴化物时循环次数为 43-2600。
• Oxygen-promoted coupling of arylboronic acids with olefins catalyzed by [CA]2[PdX4] complexes without a base
  作者：E. Silarska、A.M. Trzeciak

  DOI：10.1016/j.molcata.2015.07.003

  日期：2015.11

  An efficient method was developed for the oxidative Heck reaction between arylboronic acids and olefins catalyzed by anionic palladium complexes of the type [CA](x)[PdCl4] (x = 1,2) and [CA](2)[Pd2Cl6] (CA= imidazolium or pyridinium cation). Molecular oxygen was employed as an environmentally benign oxidant to regenerate Pd(II) species during the reaction. The elaborated protocol could be applied to the coupling of different arylboronic acids with both electron-rich and electron-poor olefins. The catalyst system was further employed for the one-pot oxidative Heck reaction followed by the Heck coupling to build conjugated compounds in good yield.Mass spectrometry (ESI-MS) and UV-vis spectroscopy was used to identify palladium-containing complexes in the reactions. A plausible reaction mechanism of the oxidative Heck reaction was proposed. (C) 2015 Elsevier B.V. All rights reserved.
• Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction
  作者：Ai-E Wang、Jian-Hua Xie、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1016/j.tet.2004.10.049

  日期：2005.1

  A new type of triaryl phosphine-functionalized imidazolium salts 6 were prepared. Their palladium complexes, generated in situ, were successfully applied in the palladium-catalyzed Heck reaction. Using 1 mol% of Pd(dba)(2) and 10 mol% 6c in the presence of 2 equiv of K2CO3 in DMAc has proven to be highly efficient for the coupling of a wide array of aryl bromides and iodides with acrylates in excellent yield. The coupling of 4-bromotoluene with various styrene derivatives catalyzed by Pd/6c complex also gave good results. (C) 2004 Elsevier Ltd. All rights reserved.