2-benzoyloxy-1-phenyl-3,3,3-trifluoro-1-propanone | 154918-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoyloxy-1-phenyl-3,3,3-trifluoro-1-propanone
• 英文别名: 2-benzoyloxy-3,3,3-trifluoro-1-phenyl-1-propanone；1-benzoyl-2,2,2-trifluoromethyl benzoate；(1,1,1-Trifluoro-3-oxo-3-phenylpropan-2-yl) benzoate
• CAS: 154918-82-8
• 化学式: C₁₆H₁₁F₃O₃
• 分子量: 308.257
• InChiKey: LMUWFLJMHATKIP-UHFFFAOYSA-N

物化性质

• 沸点：
  390.7±42.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-benzoyloxy-1-phenyl-3,3,3-trifluoro-1-propanone 在 sodium hydroxide 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 1.58h， 生成 4-phenyl-5-(trifluoromethyl)-1,3-dioxolan-2-one
  参考文献：
  名称：

  Ring-Opening of 1-CF3-Substituted Epoxy Ethers with Carboxylic, Thiocarboxylic, and Phosphinic Acids in Basic Medium and in Hexafluoro-2-propanol

  摘要：

  Ring-opening of 1-CF3-substituted epoxy ethers with carboxylic acids was achieved in Et3N as solvent, and alpha-CF3-substituted acyloins and corresponding esters were obtained in good yields. In hexafluoro-2-propanol (HFIP) as solvent, the carboxylic acids acted as nucleophiles, and alpha-carbonyloxy trifluoromethyl ketones were isolated in good yields. After reduction, CF3-substituted glycols were obtained as monoesters on one or the other hydroxy group. This reaction also allowed the preparation of alpha-carbonylsulfanyl- and alpha-phosphoryloxy trifluoromethyl ketones and corresponding alcohols. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200210)2002:20<3402::aid-ejoc3402>3.0.co;2-m
• 作为产物：
  描述：

  3,3,3-trifluoro-2-oxo-1-phenylpropyl benzoate 在 三乙胺 作用下， 反应 2.0h， 生成 2-benzoyloxy-1-phenyl-3,3,3-trifluoro-1-propanone
  参考文献：
  名称：

  Ring-Opening of 1-CF3-Substituted Epoxy Ethers with Carboxylic, Thiocarboxylic, and Phosphinic Acids in Basic Medium and in Hexafluoro-2-propanol

  摘要：

  Ring-opening of 1-CF3-substituted epoxy ethers with carboxylic acids was achieved in Et3N as solvent, and alpha-CF3-substituted acyloins and corresponding esters were obtained in good yields. In hexafluoro-2-propanol (HFIP) as solvent, the carboxylic acids acted as nucleophiles, and alpha-carbonyloxy trifluoromethyl ketones were isolated in good yields. After reduction, CF3-substituted glycols were obtained as monoesters on one or the other hydroxy group. This reaction also allowed the preparation of alpha-carbonylsulfanyl- and alpha-phosphoryloxy trifluoromethyl ketones and corresponding alcohols. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200210)2002:20<3402::aid-ejoc3402>3.0.co;2-m

文献信息

• Convenient Synthesis of .ALPHA.-Trifluoromethylated Acyloins from .ALPHA.-Hydroxy or .ALPHA.-Amino Acids.
  作者：Masami KAWASE、Setsuo SAITO、Teruo KURIHARA

  DOI：10.1248/cpb.48.1338

  日期：——

  acyloins (2 and 6) have been prepared from alpha-hydroxy acids (1), N-acylprolines (5) or N-acyl-N-alkyl alpha-amino acids (8) by novel transformation reactions with trifluoroacetic anhydride (TFAA) in the presence of pyridine. The former reaction of 1 could proceed through mesoionic 1,3-dioxolium-4-olates, whereas the latter two reactions of alpha-amino acids (5 and 8) could involve mesoionic 1,3-oxazolium-5-olates

  α-三氟甲基化酰基辅酶（2和6）是由α-羟基酸（1），N-酰基脯氨酸（5）或N-酰基-N-烷基α-氨基酸（8）与三氟乙酸酐（ TFAA）在吡啶存在下。前者1的反应可以通过1,3-二氧恶唑鎓4-olates进行，而后两个α-氨基酸（5和8）的反应可能涉及1,3-二恶唑鎓5-olates。1与TFAA的反应在实际应用中显示出更大的潜力，这是因为起始材料易于使用且易于操作。
• Unusual reactions of secondary amino acids with trifluoroacetic anhydride: A novel access to α-trifluoromethylated acyloins
  作者：Masami Kawase

  DOI：10.1016/0040-4039(94)88187-1

  日期：1994.1

  A new fragmentation reaction of secondary α-amino acids with trifluoroacetic anhydride under Dakin-West reaction conditions proceeds through oxazolium salt intermediates followed by ring cleavage to form α-trifluoromethylated acyloins in good yields.

  在Dakin-West反应条件下，仲α-氨基酸与三氟乙酸酐的新断裂反应通过恶唑鎓盐中间体进行，然后进行环裂解，以高收率形成α-三氟甲基化酰基辅酶。
• A convenient synthesis of α-trifluoremethylated and α-perfluoroalkylated acyloins from α-hydroxy acids
  作者：Masami Kawase、Teruo Kurihara

  DOI：10.1016/0040-4039(94)88284-3

  日期：1994.10

  A novel transformation of α-hydroxy acids to α-trifluoremethylated and α-perfluoroalkylated acyloins was efficiently realized by utilizing trifluoroacetic or perfluoroalkylcarboxylic anhydrides in the presence of pyridine, in which probable intermediates were meso-ionic 1,3-dioxolium-4-olates.

  通过在吡啶存在下利用三氟乙酸或全氟烷基羧酸酐，可以有效地实现α-羟基酸向α-三氟甲基化和α-全氟烷基化酰基转移的新型转化，其中可能的中间体是中离子1,3-二氧杂-4-醇盐。