1,2-di(2-n-butylcarbonyl-trans-vinyl)-benzene

• 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: 1,2-di(2-n-butylcarbonyl-trans-vinyl)-benzene
• 英文别名: 2E,2′E-3,3′-(1,2-phenylene) bis[2-propenoic acid] dibutyl ester；(E)-butyl 3-(2-((E)-3-oxo-3-butoxyprop-1-en-1-yl)phenyl)acrylate；butyl (E)-3-[2-[(E)-3-butoxy-3-oxoprop-1-enyl]phenyl]prop-2-enoate
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: PBSSCFKEPDJUDU-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-di(2-n-butylcarbonyl-trans-vinyl)-benzene 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  通过光诱导的邻二乙烯基苯的分子内Oxa- [4 + 2]环加成反应合成氧三环辛烷

  摘要：

  在室温下，取代的邻二乙烯基苯的光解促进了一步和无金属的转化为氧三环。辐照邻二乙烯基苯导致周环反应，形成环状邻喹二乙烷中间体，随后中间体进行分子内的oxa- [4 + 2]环加成反应形成oxacyclic衍生物。

  DOI：

  10.1021/acs.joc.7b01055
• 作为产物：
  描述：

  溴乙酸丁酯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 31.17h， 生成 1,2-di(2-n-butylcarbonyl-trans-vinyl)-benzene
  参考文献：
  名称：

  光诱导分子间[4 + 2]环加成反应构建苯并双环[2.2.2]辛烷骨架

  摘要：

  探索了一种新型的高效合成高度取代的苯并双环[2.2.2]辛烷骨架的方法。在紫外光照射下，邻-二乙烯基苯经历周环反应以形成环状邻-喹二甲烷中间体，随后通过[4 + 2]加成使其与烯烃反应，从而在温和条件下构建苯并双环[2.2.2]辛烷骨架。革兰氏反应证明了该方案的合成潜力。

  DOI：

  10.1021/acs.joc.6b02547

文献信息

• 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.
• Facile route to dihydroindacene type ligands using multiple Heck reactions on aryl polybromides
  作者：Alberto Ceccon、Laura Crociani、Saverio Santi、Alfonso Venzo、Andrea Biffis、Giovanni Boccaletti

  DOI：10.1016/s0040-4039(02)02087-7

  日期：2002.11

  The Heck reaction of aryl dibromides and n-butyl acrylate catalyzed by Pd(OAc2/pO-Bu), is a high yielding method to produce intermediates for dihydroindacene type ligands. The same synthetic strategy, extended to tribromides, represents a simple route also to tridentate ligands potentially useful in the stabilization of trimeric metal complexes and clusters. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons
  作者：Qiang Liu、Junlei Wang、Dazhi Li、Chao Yang、Wujiong Xia

  DOI：10.1021/acs.joc.6b02547

  日期：2017.2.3

  skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.

  探索了一种新型的高效合成高度取代的苯并双环[2.2.2]辛烷骨架的方法。在紫外光照射下，邻-二乙烯基苯经历周环反应以形成环状邻-喹二甲烷中间体，随后通过[4 + 2]加成使其与烯烃反应，从而在温和条件下构建苯并双环[2.2.2]辛烷骨架。革兰氏反应证明了该方案的合成潜力。
• Synthesis of Oxatricyclooctanes via Photoinduced Intramolecular Oxa-[4+2] Cycloaddition of Substituted <i>o</i>-Divinylbenzenes
  作者：Qiang Liu、Junlei Wang、Dazhi Li、Guo-Lin Gao、Chao Yang、Yuan Gao、Wujiong Xia

  DOI：10.1021/acs.joc.7b01055

  日期：2017.8.4

  The photolysis of substituted o-divinylbenzenes promotes a one-step and metal-free conversion to oxatricycles at room temperature. Irradiation o-divinylbenzenes results in an pericyclic reaction to form cyclic o-quinodiemthane intermediates, which subsequently undergo intramolecular oxa-[4+2] cycloaddition to form oxacyclic derivatives.

  在室温下，取代的邻二乙烯基苯的光解促进了一步和无金属的转化为氧三环。辐照邻二乙烯基苯导致周环反应，形成环状邻喹二乙烷中间体，随后中间体进行分子内的oxa- [4 + 2]环加成反应形成oxacyclic衍生物。