(Z)-4-ethoxy-4-oxobut-2-en-2-yl 2-methylbenzoate | 1086245-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-4-ethoxy-4-oxobut-2-en-2-yl 2-methylbenzoate
• 英文别名: [(Z)-4-ethoxy-4-oxobut-2-en-2-yl] 2-methylbenzoate
• CAS: 1086245-10-4
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: PXNBUSLMTVUTCL-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻二甲苯 、 乙酰乙酸乙酯 在 叔丁基过氧化氢 、 copper(II) acetate monohydrate 作用下， 以 癸烷 为溶剂， 反应 2.5h， 以88%的产率得到(Z)-4-ethoxy-4-oxobut-2-en-2-yl 2-methylbenzoate
  参考文献：
  名称：

  Directing Group Assisted Copper-Catalyzed Chemoselective O-Aroylation of Phenols and Enols Using Alkylbenzenes

  摘要：

  By using alkylbenzenes as aroyl surrogates, copper(II) catalyzed chemoselective O-aroylations of 1,3-dicarbonyl compounds and phenolic -OH ortho to carbonyl (-CHO, -COR) groups have been achieved. A dual mechanism operating in tandem for these transformations has been supported by a crossover experiment.

  DOI：

  10.1021/ol401682a

文献信息

• Copper-Catalyzed Oxidative C–O Bond Formation of 2-Acyl Phenols and 1,3-Dicarbonyl Compounds with Ethers: Direct Access to Phenol Esters and Enol Esters
  作者：Jihye Park、Sang Hoon Han、Satyasheel Sharma、Sangil Han、Youngmi Shin、Neeraj Kumar Mishra、Jong Hwan Kwak、Cheong Hoon Lee、Jeongmi Lee、In Su Kim

  DOI：10.1021/jo500576x

  日期：2014.5.16

  A copper-catalyzed oxidative coupling of 2-carbonyl-substituted phenols and 1,3-dicarbonyl compounds with a wide range of dibenzyl or dialkyl ethers is described. This protocol provides an efficient preparation of phenol esters and enol esters in good yields with high chemoselectivity. This method represents an alternative protocol for classical esterification reactions.

  描述了2-羰基取代的苯酚和1，3-二羰基化合物与各种各样的二苄基或二烷基醚的铜催化的氧化偶联。该方案以高收率和高化学选择性提供了酚酯和烯醇酯的有效制备方法。该方法代表了经典酯化反应的替代方案。
• Directing Group Assisted Copper-Catalyzed Chemoselective <i>O</i>-Aroylation of Phenols and Enols Using Alkylbenzenes
  作者：Saroj Kumar Rout、Srimanta Guin、Arghya Banerjee、Nilufa Khatun、Anupal Gogoi、Bhisma K. Patel

  DOI：10.1021/ol401682a

  日期：2013.8.16

  By using alkylbenzenes as aroyl surrogates, copper(II) catalyzed chemoselective O-aroylations of 1,3-dicarbonyl compounds and phenolic -OH ortho to carbonyl (-CHO, -COR) groups have been achieved. A dual mechanism operating in tandem for these transformations has been supported by a crossover experiment.