2-phenylbutanoyl trifluoroacetate | 35598-88-0

• 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: 2-phenylbutanoyl trifluoroacetate
• 英文别名: (2,2,2-trifluoroacetyl) 2-phenylbutanoate
• CAS: 35598-88-0
• 化学式: C₁₂H₁₁F₃O₃
• 分子量: 260.213
• InChiKey: QTVCYODDOIXLET-UHFFFAOYSA-N

物化性质

• 沸点：
  253.9±40.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-phenylbutanoyl trifluoroacetate 在 磷酸 作用下， 生成
  参考文献：
  名称：

  Toward a Clean Alternative to Friedel−Crafts Acylation:  In Situ Formation, Observation, and Reaction of an Acyl Bis(trifluoroacetyl)phosphate and Related Structures

  摘要：

  Reaction of acyl trifluoroacetates with phosphoric acid in the presence of trifluoroacetic anhydride (TFAA) leads to the ready formation of acyl bis(trifluoroacetyl)phosphates, which are powerful acylating agents. Formation of these species and the subsequent acylation reaction are carried out, without added solvent, in a single in situ reaction process. In this reaction system, anisole is rapidly acylated at ambient temperature using a variety of carboxylic acids giving the para isomer exclusively. TFAA acts as an activating agent and can be recovered from the reaction system as trifluoroacetic acid (TFA) and converted back to TFAA using a dehydrating agent, while phosphoric acid behaves as a covalent catalyst in the process. This reaction system has many features which are required elements of a clean alternative to the Friedel-Crafts process.

  DOI：

  10.1021/jo981264v
• 作为产物：
  描述：

  2-苯基丁酸 、 三氟乙酸酐 在 磷酸 作用下， 生成 2-phenylbutanoyl trifluoroacetate
  参考文献：
  名称：

  Toward a Clean Alternative to Friedel−Crafts Acylation:  In Situ Formation, Observation, and Reaction of an Acyl Bis(trifluoroacetyl)phosphate and Related Structures

  摘要：

  Reaction of acyl trifluoroacetates with phosphoric acid in the presence of trifluoroacetic anhydride (TFAA) leads to the ready formation of acyl bis(trifluoroacetyl)phosphates, which are powerful acylating agents. Formation of these species and the subsequent acylation reaction are carried out, without added solvent, in a single in situ reaction process. In this reaction system, anisole is rapidly acylated at ambient temperature using a variety of carboxylic acids giving the para isomer exclusively. TFAA acts as an activating agent and can be recovered from the reaction system as trifluoroacetic acid (TFA) and converted back to TFAA using a dehydrating agent, while phosphoric acid behaves as a covalent catalyst in the process. This reaction system has many features which are required elements of a clean alternative to the Friedel-Crafts process.

  DOI：

  10.1021/jo981264v

文献信息

• Acylation of aromatic ethers over solid acid catalysts: scope of the reaction with more complex acylating agents
  作者：Keith Smith、Gamal A. El-Hiti、Anthony J. Jayne、Michael Butters

  DOI：10.1039/b303906d

  日期：——

  Acylation of anisole with 2-phenylbutanoic acid derivatives, over zeolite catalysts, gives the corresponding 4-acyl derivatives with high regioselectivity. In an analogous way, 2,3-dihydrobenzofuran reacts with acid anhydrides or chlorides in the presence of catalytic quantities of zeolites to give the corresponding 5-acyl-2,3-dihydrobenzofurans. The zeolite can be recovered, regenerated and used again to give almost the same yield as with fresh zeolite. The reaction has been applied to the synthesis of ethyl (2,3-dihydrobenzofuran-5-yl)glyoxylate.

  在沸石催化剂的作用下，苯甲醚与 2-苯基丁酸衍生物发生酰化反应，可得到具有高区域选择性的相应 4-酰基衍生物。类似地，2,3-二氢苯并呋喃与酸酐或氯化物在沸石催化下发生反应，生成相应的 5-酰基-2,3-二氢苯并呋喃。沸石可以回收、再生和再次使用，其产量几乎与新鲜沸石相同。该反应已用于合成 (2,3-二氢苯并呋喃-5-基) 乙醛酸乙酯。