4-(1-naphthylamino)-1,1,1-trifluoro-3-pentene-2-one | 912335-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(1-naphthylamino)-1,1,1-trifluoro-3-pentene-2-one
• 英文别名: 1,1,1-trifluoro-4-(1-naphthylamino)-3-penten-2-one；(Z)-1,1,1-trifluoro-4-(naphthalen-1-ylamino)pent-3-en-2-one
• CAS: 912335-22-9
• 化学式: C₁₅H₁₂F₃NO
• 分子量: 279.262
• InChiKey: VHTHECHCUAGJTJ-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(1-naphthylamino)-1,1,1-trifluoro-3-pentene-2-one 在 氨 作用下， 生成 4-Amino-1,1,1-trifluoro-3-penten-2-one
  参考文献：
  名称：

  含氟烷基的1,3-二酮锂与胺和铵盐的反应

  摘要：

  在 20°C 的冰醋酸或甲醇中，含氟烷基的 1,3-二酮酸锂与胺或铵盐的反应为含氟烷基的 β-氨基乙烯酮提供了一条有效的合成途径。根据不同的条件，二酮酸锂与 1-aminonaphthalene 反应可生成 β-氨基乙烯酮和环缩合产物苯并[h]喹啉。后者可在不分离 β-氨基乙烯酮的情况下一步获得。

  DOI：

  10.1007/s11178-005-0365-x
• 作为产物：
  描述：

  5,5,5-三氟-4-羟基-戊-3-烯-2-酮 、 1-萘胺 以 甲醇 为溶剂， 以80%的产率得到4-(1-naphthylamino)-1,1,1-trifluoro-3-pentene-2-one
  参考文献：
  名称：

  Interaction of fluoroalkyl-containing ?-diketones with amines

  摘要：

  The composition of products of the interaction of asymmetric fluoroalkyl-containing beta-diketones with amines was studied. Mixtures of regioisomeric beta-aminovinylketones and products of cleavage and secondary condensation are formed, depending on the temperature, the solvent, the nature of the fluorinated and nonfluorinated substituents in the beta-diketone, and the basicity of the amine. The major product is a beta-aminovinylketone in which the NH2 group is removed from the fluoroalkyl substituent. No beta-aminovinylimines, products of condensation involving two electrophilic centers, were observed.

  DOI：

  10.1007/bf01430731

文献信息

• Interaction of fluoroalkyl-containing ?-diketones with amines
  作者：V. I. Filyakova、Y. G. Ratner、N. S. Karpenko、K. I. Pashkevich

  DOI：10.1007/bf01430731

  日期：1996.9

  The composition of products of the interaction of asymmetric fluoroalkyl-containing beta-diketones with amines was studied. Mixtures of regioisomeric beta-aminovinylketones and products of cleavage and secondary condensation are formed, depending on the temperature, the solvent, the nature of the fluorinated and nonfluorinated substituents in the beta-diketone, and the basicity of the amine. The major product is a beta-aminovinylketone in which the NH2 group is removed from the fluoroalkyl substituent. No beta-aminovinylimines, products of condensation involving two electrophilic centers, were observed.
• Fluoroalkyl-Containing Lithium 1,3-Diketonates in Reactions with Amines and Ammonium Salts
  作者：N. S. Boltacheva、V. I. Filyakova、V. N. Charushin

  DOI：10.1007/s11178-005-0365-x

  日期：2005.10

  Reactions of fluoroalkyl-containing lithium 1,3-diketonates with amines or ammonium salts in glacial acetic acid or methanol at 20°C provide an efficient synthetic route to fluoroalkyl-containing β-amino-vinyl ketones. Depending on the conditions, reactions of lithium diketonates with 1-aminonaphthalene lead to formation of both β-aminovinyl ketones and cyclocondensation products, benzo[h]quinolines. The latter can be obtained in one step without isolation of β-aminovinyl ketones.

  在 20°C 的冰醋酸或甲醇中，含氟烷基的 1,3-二酮酸锂与胺或铵盐的反应为含氟烷基的 β-氨基乙烯酮提供了一条有效的合成途径。根据不同的条件，二酮酸锂与 1-aminonaphthalene 反应可生成 β-氨基乙烯酮和环缩合产物苯并[h]喹啉。后者可在不分离 β-氨基乙烯酮的情况下一步获得。