1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl benzoate | 93876-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl benzoate
• 英文别名: Benzoyloxy-benzoyl-essigsaeure-aethylester；(1-Ethoxy-1,3-dioxo-3-phenylpropan-2-yl) benzoate
• CAS: 93876-30-3
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: JBJVPIIPFXOSPE-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C(Solv: ethanol, 95% (64-17-5))
• 沸点：
  473.0±35.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl benzoate 、 水 生成 (2-氧代-2-苯基乙基)苯甲酸酯
  参考文献：
  名称：

  Bradley; Robinson, Journal of the Chemical Society, 1928, p. 1551

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 5,6-二甲基-1H-苯并三唑水合物 、 过氧化苯甲酰 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以28%的产率得到1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl benzoate
  参考文献：
  名称：

  Metal-free cross-dehydrogenative C–N coupling of azoles with xanthenes and related activated arylmethylenes

  摘要：

  A metal-free C(sp(3))-H/N-H cross-coupling of azoles with xanthenes and related activated arylmethylenes is presented. Both the use of azoles and the activation pattern of C(sp(3))-H sources are essential for this transformation. In the presence of 2.0 equiv of benzoyl peroxide (BPO), methylenes bearing a heteroatom-bridged bisaryl group reacted with various azolic N-H sources to afford C-N bond forming products in usually excellent or quantitative yields, and the diphenylmethane and methylenes coactivated by a phenyl group and an adjacent heteroatom are less reactive. Mechanistic investigations suggest that a radical/radical cross-coupling pathway might be involved.[GRAPHICS].

  DOI：

  10.1080/00397911.2019.1615097

文献信息

• Bu₄NI-Catalyzed α-Oxyacylation of Carbonyl Compounds with Toluene Derivatives
  作者：Chengliang Li、Tao Jin、Xinglu Zhang、Chunju Li、Xueshun Jia、Jian Li

  DOI：10.1021/acs.orglett.6b00749

  日期：2016.4.15

  A TBAI (tetrabutylammonium iodide)-catalyzed direct α-oxyacylation of carbonyl compounds from readily available toluene derivatives has been developed. The distinguished features of this metal-free protocol include the employment of simple starting material, a wide carbonyl compound scope, and mild reaction conditions.

  已经开发了TBAI（碘化四丁基铵）从容易获得的甲苯衍生物中催化羰基化合物的直接α-氧酰化。该无金属方案的显着特征包括采用简单的起始原料，广泛的羰基化合物范围和温和的反应条件。
• TBAI-catalyzed oxidative coupling of β-ketoesters with carboxylic acid: synthesis of α-carboxylic-β-ketoesters
  作者：Xiaoqing Li、Can Zhou、Xiangsheng Xu

  DOI：10.3998/ark.5550190.0013.913

  日期：——

  TBAI-catalyzed oxidative coupling of β-ketoesters with carboxylic acid using TBHP as oxidant has been established. This transformation provides a facile and direct strategy for the synthesis of α-carboxylic-β-ketoesters.

  已经建立了使用 TBHP 作为氧化剂的 TBAI 催化的 β-酮酯与羧酸的氧化偶联。这种转化为α-羧基-β-酮酯的合成提供了一种简便而直接的策略。
• Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids
  作者：Oleg V. Bityukov、Olesya K. Matveeva、Vera A. Vil’、Vladimir A. Kokorekin、Gennady I. Nikishin、Alexander O. Terent’ev

  DOI：10.1021/acs.joc.8b02791

  日期：2019.2.1

  The electrochemically induced cross-dehydrogenative C–O coupling of β-diketones and β-ketoesters (C–H reagents) with carboxylic acids (O–H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C–O coupling products in high yields, up to 92%, using DMSO as a solvent with a broad substrate scope in an undivided cell equipped with carbon and platinum

  已开发出β-二酮和β-酮​​酸酯（C-H试剂）与羧酸（OH试剂）的电化学诱导的交叉脱氢C-O偶联。该反应的一个重要特征在于，使用DMSO作为溶剂，在高电流下配有碳和铂电极的未分割电池中，使用DMSO作为溶剂，可以选择性地形成高达92％的高产率分子间C-O偶联产物。密度。电流充当化学计量的氧化剂。
• Copper-catalyzed α-C–H acyloxylation of carbonyl compounds with terminal alkynes
  作者：Jiao Li、Zan Yang、Tao Yang、Jianmin Yi、Congshan Zhou

  DOI：10.1039/c7nj03989a

  日期：——

  Herein, a copper/TBHP catalyst system for the α-C–H acyloxylation of carbonyl compounds is developed using terminal alkynes as the acyloxy source. A variety of carbonyl compounds and terminal alkynes are tolerated in this reaction. In addition, its possible mechanism is proposed.

  在此，使用末端炔烃作为酰氧基源，开发了用于羰基化合物的α-C-H酰氧基化的铜/ TBHP催化剂体系。在该反应中可以耐受多种羰基化合物和末端炔烃。另外，提出了其可能的机制。
• One-pot synthesis of α-acyloxycarbonyl compounds via oxidative decarboxylation coupling reaction of α-oxo carboxylic acids with carbonyl compounds
  作者：Li-Ming Chang、Gao-Qing Yuan

  DOI：10.1016/j.tet.2016.09.031

  日期：2016.11

  With tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, a simple metal-free protocol has been developed for the synthesis of α-acyloxycarbonyl compounds from carbonyl compounds and α-oxo carboxylic acids via decarboxylative coupling reaction. The target products could be obtained in moderate to high yields.

  以碘化四丁基铵（TBAI）为催化剂，叔丁基过氧化氢（TBHP）为氧化剂，已开发出一种简单的无金属方案，用于通过脱羧偶联从羰基化合物和α-氧代羧酸合成α-酰氧羰基化合物反应。可以以中等至高收率获得目标产物。