butyl (E)-3-{2-[(dimethylcarbamoyl)oxy]phenyl}acrylate | 1309752-06-4

• 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: butyl (E)-3-{2-[(dimethylcarbamoyl)oxy]phenyl}acrylate
• 英文别名: (E)-butyl 3-(2-(dimethylcarbamoyloxy)phenyl)acrylate；butyl (E)-3-[2-(dimethylcarbamoyloxy)phenyl]prop-2-enoate
• CAS: 1309752-06-4
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: IOKZSTWVJAVSFI-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯酚 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 、 三乙胺 作用下， 以 四氢吡喃 、 氯仿 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 butyl (E)-3-{2-[(dimethylcarbamoyl)oxy]phenyl}acrylate
  参考文献：
  名称：

  Rhodium-Catalyzed Selective C–H Activation/Olefination of Phenol Carbamates

  摘要：

  Rh(III)-catalyzed ortho C-H activation/olefination of phenol carbamates has been developed. High regioselectivity is observed with a range of phenol carbamates enabling efficient coupling with acrylates and styrenes. This reaction exhibits different reactivity as compared to the Pd-catalyzed ortho-arylation reaction of phenol esters and provides a new approach for the synthesis of ortho-substituted phenols.

  DOI：

  10.1021/ol201140q

文献信息

• Rhodium(III)-Catalyzed Oxidative <i>ortho</i>-Olefination of Phenyl Carbamates with Alkenes: Elucidation of Acceleration Mechanisms by Using an Unsubstituted Cyclopentadienyl Ligand
  作者：Jin Tanaka、Yuki Nagashima、Ken Tanaka

  DOI：10.1021/acs.orglett.0c02499

  日期：2020.9.18

  It has been established that an unsubstituted cyclopentadienyl (Cp) Rh(III) complex is an effective catalyst for the oxidative ortho-olefination of phenyl carbamates with both acrylates and styrenes under mild conditions. In addition, diolefination of a protected BINOL (1,1′-binaphthalene-2,2′-diol) proceeded in high yields and disubstituted acrylates could participate in this catalysis. Experimental

  已经确定，在温和条件下，未取代的环戊二烯基（Cp）Rh（III）配合物是苯基氨基甲酸酯与丙烯酸酯和苯乙烯的氧化邻位烯烃聚合的有效催化剂。此外，受保护的BINOL（1,1'-联萘-2,2'-二醇）的二烯化反应产率很高，二取代的丙烯酸酯可参与该催化作用。实验和理论机理研究表明，未取代的CpRh（III）络合物的电子缺陷性质会加速亲电芳基CH的铑化反应和限速烯烃的插入步骤。
• Rhodium-Catalyzed Selective C–H Activation/Olefination of Phenol Carbamates
  作者：Tian-Jun Gong、Bin Xiao、Zhao-Jing Liu、Jian Wan、Jun Xu、Dong-Fen Luo、Yao Fu、Lei Liu

  DOI：10.1021/ol201140q

  日期：2011.6.17

  Rh(III)-catalyzed ortho C-H activation/olefination of phenol carbamates has been developed. High regioselectivity is observed with a range of phenol carbamates enabling efficient coupling with acrylates and styrenes. This reaction exhibits different reactivity as compared to the Pd-catalyzed ortho-arylation reaction of phenol esters and provides a new approach for the synthesis of ortho-substituted phenols.