2-(2-fluorophenyl)-2-oxoethyl acetate | 711-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-fluorophenyl)-2-oxoethyl acetate
• 英文别名: 2-Fluor-phenacyl-acetat；o-fluorophenacyl acetate；α-acetoxy-2-fluoroacetophenone；[2-(2-Fluorophenyl)-2-oxoethyl] acetate；[2-(2-fluorophenyl)-2-oxoethyl] acetate
• CAS: 711-90-0
• 化学式: C₁₀H₉FO₃
• mdl: MFCD22987646
• 分子量: 196.178
• InChiKey: KMNWOIQIBNKUIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-fluorophenyl)-2-oxoethyl acetate 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 以81%的产率得到1-(2-氟苯基)-2-羟基乙烷酮
  参考文献：
  名称：

  Synthesis of α-Hydroxyacetophenones

  摘要：

  A general method for the preparation of alpha-hydroxyacetophenones is presented. Functionalized arylmagnesium species are transmetalated to the corresponding arylzinc intermediates, which undergo Cu(I)-catalyzed reaction with acetoxyacetyl chloride. Acidic hydrolysis of the acetate group releases the target alpha-hydroxyacetophenones with minimal production of undesired polymeric degradates that are often observed under alternative conditions.

  DOI：

  10.1021/jo3005556
• 作为产物：
  描述：

  1-乙炔基-2-氟苯 在 水 作用下， 以 二氯甲烷 为溶剂， 反应 12.67h， 生成 2-(2-fluorophenyl)-2-oxoethyl acetate
  参考文献：
  名称：

  硫介导的内部和末端炔烃双官能团合成α-乙酰氧基酮

  摘要：

  据报道，炔烃的硫介导的双官能团化可以在温和的条件下，通过一锅操作以19-92％的收率得到α-乙酰氧基酮。通过使用湿乙酸钾作为碱水溶液和亲核试剂，末端炔烃和内部炔烃都可以转化为α-乙酰氧基酮产物。

  DOI：

  10.1016/j.tetlet.2020.151707

文献信息

• Decarboxylative Oxyacyloxylation of Propiolic Acids: Construction of Alkynyl-Containing α-Acyloxy Ketones
  作者：Xin Chen、Yangchun Xin、Zhi-Wei Zhao、Yu-Jian Hou、Xiang-Xiang Wang、Wen-Jin Xia、Ya-Min Li

  DOI：10.1021/acs.joc.1c00669

  日期：2021.6.18

  Novel decarboxylative oxyacyloxylation of propiolic acids has been developed. This reaction provides an efficient access to alkynyl-containing α-acyloxy ketones from readily available starting materials and exhibits significant functional group tolerance. Furthermore, oxyacyloxylation of terminal alkynes and aliphatic propiolic acids was also developed. A possible reaction mechanism is proposed based

  已开发出丙炔酸的新型脱羧氧基酰氧基化。该反应提供了从容易获得的起始材料中有效获取含炔基的 α-酰氧基酮的途径，并表现出显着的官能团耐受性。此外，还开发了末端炔烃和脂肪族丙炔酸的氧酰氧基化。基于机理研究提出了一种可能的反应机理。
• Copper(II) and 2,2′-Biimidazole-promoted Novel Reaction of 4,4,4-Trifluoro-1-phenylbutane-1,3-diones with Iodobenzene Diacetate
  作者：Chunmei Zhou、Runsheng Zeng、Jianping Zou

  DOI：10.1002/cjoc.201090069

  日期：2010.2

  A new and efficient way was developed to carry out the reaction of 4,4,4‐trifluoro‐1‐phenylbutane‐1,3‐dione with iodobenzene diacetate under the assistance of Cu(II) and 2,2′‐biimidazole at a low temperature in excellent yield. 2‐Acetoxyacetophenone was obtained unexpectedly.

  在Cu（II）和2,2'-联咪唑的协助下，开发了一种新的高效方法来进行4,4,4-三氟-1-苯基丁烷-1,3-二酮与碘代苯二乙酸的反应。低温，产率高。意外地获得了2-乙酰氧基苯乙酮。
• Synthesis of α-Hydroxyacetophenones
  作者：Mark McLaughlin、Kevin M. Belyk、Gang Qian、Robert A. Reamer、Cheng-yi Chen

  DOI：10.1021/jo3005556

  日期：2012.6.1

  A general method for the preparation of alpha-hydroxyacetophenones is presented. Functionalized arylmagnesium species are transmetalated to the corresponding arylzinc intermediates, which undergo Cu(I)-catalyzed reaction with acetoxyacetyl chloride. Acidic hydrolysis of the acetate group releases the target alpha-hydroxyacetophenones with minimal production of undesired polymeric degradates that are often observed under alternative conditions.
• Sulfur-mediated difunctionalization of internal and terminal alkynes for the synthesis of α-acetoxy ketones
  作者：Zhong Zhang、Pingfan Li

  DOI：10.1016/j.tetlet.2020.151707

  日期：2020.4

  The sulfur-mediated difunctionalization of alkynes is reported to give α-acetoxy ketones in a one-pot operation under mild conditions with 19-92% yield. By using wet potassium acetate as both the aqueous base and nucleophilic reagent, both terminal alkynes and internal alkynes could be converted into the α-acetoxy ketone products.

  据报道，炔烃的硫介导的双官能团化可以在温和的条件下，通过一锅操作以19-92％的收率得到α-乙酰氧基酮。通过使用湿乙酸钾作为碱水溶液和亲核试剂，末端炔烃和内部炔烃都可以转化为α-乙酰氧基酮产物。