4-fluoro-5-methoxycyclohex-4-ene-1,1,2,2-tetracarbonitrile

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 4-fluoro-5-methoxycyclohex-4-ene-1,1,2,2-tetracarbonitrile
• 英文别名: 4-Fluoro-5-methoxycyclohex-4-ene-1,1,2,2-tetracarbonitrile
• 化学式: C₁₁H₇FN₄O
• 分子量: 230.201
• InChiKey: OZMGPWUEBORJFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-fluoro-5-methoxycyclohex-4-ene-1,1,2,2-tetracarbonitrile 以 水 、 乙腈 为溶剂， 反应 0.33h， 以60%的产率得到4-fluoro-5-oxocyclohexane-1,1,2,2-tetracarbonitrile
  参考文献：
  名称：

  Microwave assisted Diels-Alder cycloaddition of 2-fluoro-3-methoxy-1,3-butadiene

  摘要：

  The title fluorodiene (2) reacts with several dienophiles in moderate yields (20-65%, 0.5 h to 3d) when thermal activation is used. When 100 W microwave radiation is used the reaction yields (70-90%, 5-25 min) are greatly improved and the reaction times are much shorter. A microwave procedure is also used for the hydrolysis of vinyl ether cycloadducts to alpha-fluoroketones. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.03.010
• 作为产物：
  描述：

  1-氯-1-氟-2-甲氧基-2-甲基环丙烷 在 喹啉 作用下， 以 氘代氯仿 为溶剂， 反应 6.0h， 生成 4-fluoro-5-methoxycyclohex-4-ene-1,1,2,2-tetracarbonitrile
  参考文献：
  名称：

  A Convenient Preparation of 2-Fluoro-3-alkoxy-1,3-butadienes

  摘要：

  [GRAPHICS]1-Chloro-1-fluoro-2-methoxy-2-methylcyclopropane eliminates HCl on heating in quinoline solution above 50 degreesC to give 2-fluoro-3-methoxy-1,3-butadiene in high yield. If an alcohol is added to the reaction then a 2-fluoro-3-alkoxy-1,3-butadiene is obtained in high yield. The dienes give smooth 4 + 2 cycloaddition reactions.

  DOI：

  10.1021/ol026512v

文献信息

• Microwave assisted Diels-Alder cycloaddition of 2-fluoro-3-methoxy-1,3-butadiene
  作者：Timothy B. Patrick、Keith Gorrell、James Rogers

  DOI：10.1016/j.jfluchem.2007.03.010

  日期：2007.7

  The title fluorodiene (2) reacts with several dienophiles in moderate yields (20-65%, 0.5 h to 3d) when thermal activation is used. When 100 W microwave radiation is used the reaction yields (70-90%, 5-25 min) are greatly improved and the reaction times are much shorter. A microwave procedure is also used for the hydrolysis of vinyl ether cycloadducts to alpha-fluoroketones. (c) 2007 Elsevier B.V. All rights reserved.
• A Convenient Preparation of 2-Fluoro-3-alkoxy-1,3-butadienes
  作者：Timothy B. Patrick、James Rogers、Keith Gorrell

  DOI：10.1021/ol026512v

  日期：2002.9.1

  [GRAPHICS]1-Chloro-1-fluoro-2-methoxy-2-methylcyclopropane eliminates HCl on heating in quinoline solution above 50 degreesC to give 2-fluoro-3-methoxy-1,3-butadiene in high yield. If an alcohol is added to the reaction then a 2-fluoro-3-alkoxy-1,3-butadiene is obtained in high yield. The dienes give smooth 4 + 2 cycloaddition reactions.