4-(1,1-dimethylethyl)-2-trifluoroacetyl-1-methoxycyclohexene | 873312-17-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-(1,1-dimethylethyl)-2-trifluoroacetyl-1-methoxycyclohexene
• 英文别名: 1-(5-Tert-butyl-2-methoxycyclohexen-1-yl)-2,2,2-trifluoroethanone
• CAS: 873312-17-5
• 化学式: C₁₃H₁₉F₃O₂
• 分子量: 264.288
• InChiKey: ISAYENZCNILHLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(1,1-dimethylethyl)-2-trifluoroacetyl-1-methoxycyclohexene 、 尿素 在 三氟化硼乙醚 作用下， 以 异丙醇 为溶剂， 反应 20.0h， 以50%的产率得到6-(1,1-dimethylethyl)-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
• 作为产物：
  描述：

  4-叔丁基环己酮 在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 40.0h， 生成 4-(1,1-dimethylethyl)-2-trifluoroacetyl-1-methoxycyclohexene
  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, 17O NMR spectroscopy and structure of 2-trifluoroacetyl-1-methoxycycloalkenes
  作者：Helio G. Bonacorso、Michelle B. Costa、Sidnei Moura、Lucas Pizzuti、Marcos A.P. Martins、Nilo Zanatta、Alex F.C. Flores

  DOI：10.1016/j.jfluchem.2005.08.003

  日期：2005.10

  Among the synthesis of a series of five well-known 2-trifluoroacetyl-1-methoxycycloalkenes derived from cyclopentanone and substituted cyclohexanones, this paper describes the synthesis of three new 2-trifluoroacetyl-1-methoxycycloalkenes derived from cycloheptanone, cyclooctanone and cyclododecanone in 60-68% yield. Subsequently, the O-17 NMR chemical shift analysis of the carbonyl and the methoxy groups for these cyclic molecules clearly showed the electron push-pull phenomenon and revealed large and irregular variations of O-17 NMR chemical shifts with the ring size. Finally, a more stable conformation of these trifluoroacetyl-containing cycloalkenes was determined by energy minimization calculations using Austin Model 1 (AM1) semi-empirical method and correlations between O-17 NMR data and torsion angles or oxygen net charge calculated by AMI semi-empirical method were performed. (c) 2005 Elsevier B.V. All rights reserved.
• 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.