1,4-bis(2-(allyloxy)phenoxy)but-2-ene | 185146-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-bis(2-(allyloxy)phenoxy)but-2-ene
• 英文别名: 1,1'-[But-2-ene-1,4-diylbis(oxy)]bis{2-[(prop-2-en-1-yl)oxy]benzene}；1-prop-2-enoxy-2-[4-(2-prop-2-enoxyphenoxy)but-2-enoxy]benzene
• CAS: 185146-74-1
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: RWOQZWOFAHFXQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2-二(烯丙氧基)苯 在 Grubbs catalyst first generation 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.08h， 以85%的产率得到2,5-dihydrobenzo-1,6-dioxocin
  参考文献：
  名称：

  An Investigation of Wall Effects in Microwave-Assisted Ring-Closing Metathesis and Cyclotrimerization Reactions

  摘要：

  Challenging Ru-catalyzed ring-closing metathesis transformations leading to eight-membered-ring systems and Ni- or Co-catalyzed [2+2+2] cyclotrimerizations were evaluated at elevated temperatures applying microwave dielectric heating or conventional thermal heating in order to investigate the role of wall effects. All reactions were conducted in a dedicated reactor setup that allowed accurate internal reaction temperature measurements using fiber-optic probes for both types of heating modes. For ring-closing metathesis best results were achieved using an open vessel gas sparging protocol in 1,2-dichloroethane at reflux temperature (83 degrees C), while cyclotrimerizations were performed under sealed vessel conditions in toluene between 80 and 160 degrees C. For all studied transformations the results achieved in a single-mode microwave reactor could be reproduced by conventional heating in an oil bath by carefully matching the temperature profiles as close as possible during the entire heating and cooling cycle. In contrast to previous literature reports, no evidence that direct in-core microwave heating can increase catalyst lifetime by minimization or elimination of wall effects was obtained. At the same time, no indication for the involvement of nonthermal microwave effects in these homogeneous transition metal-catalyzed transformations was seen.

  DOI：

  10.1021/jo1011703