4-trifluoromethyl-5,6,7,8-tetrahydro-2(1H)-quinazolinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-trifluoromethyl-5,6,7,8-tetrahydro-2(1H)-quinazolinone
• 英文别名: 4-(Trifluoromethyl)-5,6,7,8-tetrahydroquinazolin-2-ol；4-(trifluoromethyl)-5,6,7,8-tetrahydro-1H-quinazolin-2-one
• 化学式: C₉H₉F₃N₂O
• mdl: MFCD04116487
• 分子量: 218.178
• InChiKey: KAWUGKMBYWDAGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二乙基-4-氨基苯甲醛 、 4-trifluoromethyl-5,6,7,8-tetrahydro-2(1H)-quinazolinone 在 三氟化硼乙醚 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 以57%的产率得到8-(E)-(p-Diethylaminobenzylidene)-5,6,7,8-tetrahydro-2-hydroxy-4-(trifluoromethyl)quinazoline
  参考文献：
  名称：

  Syntheses of Novel 4-Polfluoroalkyl-Substituted 5,6-Oligomethylene Pyrimidines

  摘要：

  含有多氟烷基团的2-酰基环烷酮与胍、尿素、硫脲、甲基异硫脲、苯基胍、氨基硫脲、二氰二胺和三氟乙酰尿素在路易斯酸催化下反应，形成相应的5,6-聚甲烯基嘧啶。观察到随着起始1,3-二酮分子中多氟烷基取代基长度的增加，对于核能性较低的试剂（如尿素、硫脲和二氰二胺），产率下降。由芳香醛获得的嘧啶相较于芳基烯烃双键显示E-构型。通过X射线衍射、红外光谱和核磁共振光谱研究了嘧啶环中2位取代基的变化对其互变异构体结构的影响，涉及液态和固态。

  DOI：

  10.1055/s-2000-8200
• 作为产物：
  描述：

  环己酮二甲缩酮 在 三氟化硼乙醚 吡啶 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 36.0h， 生成 4-trifluoromethyl-5,6,7,8-tetrahydro-2(1H)-quinazolinone
  参考文献：
  名称：

  Synthesis of Tetrahydro‐2(1H)quinazolinones, Cyclopenta[d]‐2(1H)pyrimidinones, and Their Thioxo Analogs from 2‐Trifluoroacetyl‐1‐methoxycycloalkenes

  摘要：

  A series of six (8)-alkyl-4-trifluoromethyl-5,6,7,8-tetrahydro-2(1H)quinazolinones, 4-trifluoromethyl-cyclopenta[d]-2(1H)pyrimidinones, and their thioxo analogs from the reaction of five beta-alkoxyvinyl trifluoromethyl ketones, derived from alkylated cyclohexanones and cyclopentanone with urea and thiourea, is reported. The reactions were carried out in a single step in propan-2-ol as solvent and boron trifluoride diethyl etherate as catalyst in 18-65% yield.

  DOI：

  10.1080/00397910500278818

文献信息

• Synthesis of Tetrahydro‐2(1<i>H</i>)quinazolinones, Cyclopenta[<i>d</i>]‐2(1<i>H</i>)pyrimidinones, and Their Thioxo Analogs from 2‐Trifluoroacetyl‐1‐methoxycycloalkenes
  作者：Helio G. Bonacorso、Michelle B. Costa、Itamar S. Lopes、Marlí R. Oliveira、Roberta L. Drekener、Marcos A. P. Martins、Nilo Zanatta、Alex F. C. Flores

  DOI：10.1080/00397910500278818

  日期：2005.12

  A series of six (8)-alkyl-4-trifluoromethyl-5,6,7,8-tetrahydro-2(1H)quinazolinones, 4-trifluoromethyl-cyclopenta[d]-2(1H)pyrimidinones, and their thioxo analogs from the reaction of five beta-alkoxyvinyl trifluoromethyl ketones, derived from alkylated cyclohexanones and cyclopentanone with urea and thiourea, is reported. The reactions were carried out in a single step in propan-2-ol as solvent and boron trifluoride diethyl etherate as catalyst in 18-65% yield.
• Syntheses of Novel 4-Polfluoroalkyl-Substituted 5,6-Oligomethylene Pyrimidines
  作者：Dmitrii V. Sevenard、Oleg G. Khomutov、Olga V. Koryakova、Valeriya V. Sattarova、Mikhail I. Kodess、Johannes Stelten、Ildiko Loop、Enno Lork、Kazimir I. Pashkevich、Gerd-Volker Röschenthaler

  DOI：10.1055/s-2000-8200

  日期：——

  2-Acylcycloalkanones having polyfluoroalkyl groups react with guanidine, urea, thiourea, methylisothiourea, benzamidine, guanylthiourea, dicyanodiamide, and trifluoroacetylurea by Lewis-acid catalysis to form the corresponding 5,6-oligomethylene pyrimidines. A decrease in the yields along with increase of polyfluoroalkyl substituent length in the molecule of the starting 1,3-diketone was observed in the case of reagents with lower nucleophilicity (urea, thiourea, dicyanodiamide). The pyrimidines obtained from aromatic aldehydes showed E-configuration with respect to the arylidene double bond. Tautomeric structures as a function of the substituent in 2 position in the pyrimidine ring both in liquid and solid state were investigated by X-ray diffraction, IR and NMR spectroscopy.

  含有多氟烷基团的2-酰基环烷酮与胍、尿素、硫脲、甲基异硫脲、苯基胍、氨基硫脲、二氰二胺和三氟乙酰尿素在路易斯酸催化下反应，形成相应的5,6-聚甲烯基嘧啶。观察到随着起始1,3-二酮分子中多氟烷基取代基长度的增加，对于核能性较低的试剂（如尿素、硫脲和二氰二胺），产率下降。由芳香醛获得的嘧啶相较于芳基烯烃双键显示E-构型。通过X射线衍射、红外光谱和核磁共振光谱研究了嘧啶环中2位取代基的变化对其互变异构体结构的影响，涉及液态和固态。

表征谱图