2,2,2-trifluoro-1-(8-pyrrolidin-1-ylbicyclo[4.2.0]oct-7-en-7-yl)ethanone | 1229115-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2,2,2-trifluoro-1-(8-pyrrolidin-1-ylbicyclo[4.2.0]oct-7-en-7-yl)ethanone
• 英文别名: 2,2,2-Trifluoro-1-(8-pyrrolidin-1-yl-7-bicyclo[4.2.0]oct-7-enyl)ethanone；2,2,2-trifluoro-1-(8-pyrrolidin-1-yl-7-bicyclo[4.2.0]oct-7-enyl)ethanone
• CAS: 1229115-77-8
• 化学式: C₁₄H₁₈F₃NO
• 分子量: 273.298
• InChiKey: ILMLRSDQWHYNGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(8-pyrrolidin-1-ylbicyclo[4.2.0]oct-7-en-7-yl)ethanone 在 lithium aluminium tetrahydride 、 sodium dihydrogenphosphate 作用下， 以 乙醚 为溶剂， 反应 0.83h， 以70%的产率得到1-(bicyclo[4.2.0]-oct-7-en-7-yl)-2,2,2-trifluoroethanone
  参考文献：
  名称：

  具有环丁烯结构的新型α，β-不饱和三氟甲基酮的合成及其在制备双环三氟甲基化吡咯中的应用

  摘要：

  用LiAlH 4部分还原应变的β-吡咯烷基-α，β-不饱和三氟甲基酮，得到相应的α，β-不饱和三氟甲基酮。它们在Mg（ClO 4）2存在下与1-（亚甲基氨基）吡咯烷的相互作用通过几个中间步骤进行，得到三氟甲基化的吡咯，其与取代的环丁烯片段缩合。

  DOI：

  10.1016/j.jfluchem.2017.12.007

文献信息

• Synthesis of novel β-dialkylamino-α,β-unsaturated trifluoromethylketones containing cyclobutene fragment and their reactions with organolithium and Grignard reagents
  作者：Andrey B. Koldobskii、Nikolai P. Tsvetkov、Ekaterina V. Solodova、Pavel V. Verteletskii、Ivan A. Godovikov、Valery N. Kalinin

  DOI：10.1016/j.tet.2010.03.026

  日期：2010.5

  from the corresponding β-halogeno-α,β-unsaturated trifluoromethylketones in almost quantitative yields. The ambident properties of these compounds in the reactions with organolithiums were discovered. The simple methods to control the selectivity of 1,2- or 1,4-addition of lithiated nucleophiles have been investigated.

  首先从相应的β-卤代-α，β-不饱和三氟甲基酮以几乎定量的产率制备具有高反应性的三氟甲基烯氨基酮，并带有应变的环丁烯和降冰片二烯部分。发现这些化合物在与有机锂反应中的环境性质。已经研究了控制锂化亲核试剂的1,2-或1,4-加成选择性的简单方法。
• The general approach for the synthesis of substituted cyclobutenyl- and norbornadienyllithiums containing masked trifluoromethyl group
  作者：Andrey B. Koldobskii、Ekaterina V. Solodova、Pavel V. Verteletskii、Ivan A. Godovikov、Valery N. Kalinin

  DOI：10.1016/j.tet.2010.10.024

  日期：2010.12

  alpha,beta-Unsaturated trifluoromethylketones of cyclobutene number containing trimethylstannyl substituent in beta-position were firstly prepared by the addition of trimethylstannyllithium to the corresponding trifluoromethylenaminoketones. The protection of carbonyl function under basic conditions conserving the organometallic substituent was elaborated. The generation of corresponding organolithiums by Sn-Li exchange and their reactivity was studied. (C) 2010 Elsevier Ltd. All rights reserved,
• Synthesis of novel α,β-unsaturated trifluoromethylketones with cyclobutene structure and their use for the preparation of bicyclic trifluoromethylated pyrroles
  作者：Andrey B. Koldobskii、Olga S. Shilova、Ekaterina V. Solodova、Pavel V. Verteletskii、Ivan A. Godovikov、Valery N. Kalinin

  DOI：10.1016/j.jfluchem.2017.12.007

  日期：2018.3

  β-unsaturated trifluoromethyl ketones. Their interaction with 1-(methyleneamino)pyrrolidine in the presence of Mg(ClO4)2 proceeds through the several intermediate steps to afford trifluoromethylated pyrroles, condensed with substituted cylobutene fragments.

  用LiAlH 4部分还原应变的β-吡咯烷基-α，β-不饱和三氟甲基酮，得到相应的α，β-不饱和三氟甲基酮。它们在Mg（ClO 4）2存在下与1-（亚甲基氨基）吡咯烷的相互作用通过几个中间步骤进行，得到三氟甲基化的吡咯，其与取代的环丁烯片段缩合。