5-(dimethylamino)-1,5-dicyclopropyl-3-ethoxy-1,3-cyclopentadiene | 173466-24-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(dimethylamino)-1,5-dicyclopropyl-3-ethoxy-1,3-cyclopentadiene
• 英文别名: 1,2-dicyclopropyl-4-ethoxy-N,N-dimethylcyclopenta-2,4-dien-1-amine
• CAS: 173466-24-5
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: ISKWNRHEZHGTTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(dimethylamino)-1,5-dicyclopropyl-3-ethoxy-1,3-cyclopentadiene 在 盐酸 、 sodium tetrahydroborate 、 cerium(III) chloride 、 溴 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 5.52h， 生成 4-cyclopropyl-4-(dimethylamino)-3-(3'-bromopropylidene)-1-cyclopentene
  参考文献：
  名称：

  Unprecedented Regio- and Stereoselective Conversion of 1-Cyclopropyl-3-ethoxycyclopentadienes to 3-(E)-Alkylidenecyclopentenes

  摘要：

  Cyclopropylalkynes 1 were converted into cyclopropyl-substituted 3-ethoxy-5-dimethylaminocyclopentadienes 4 via initially formed (beta-dimethylaminoethenyl)carbene complexes 3 and their subsequent-formal [3 + 2] cycloaddition to a second alkyne of type 1 (overall yields 51-59%). New regio- and stereoselective 1,7-addition and 1,6-substitution reactions have been developed that convert cyclopentadienes 4 into highly functionalized cyclopentenes 5 and 11, respectively (yields 98-99% and 61%, respectively). An in situ domino reaction consisting of a [3 + 2] cycloaddition and subsequent 1,7-addition has also been achieved (86% overall yield).

  DOI：

  10.1021/jo980938z
• 作为产物：
  描述：

  环丙乙炔 、 alkaline earth salt of/the/ methylsulfuric acid 以 正己烷 为溶剂， 反应 20.0h， 以95%的产率得到5-(dimethylamino)-1,5-dicyclopropyl-3-ethoxy-1,3-cyclopentadiene
  参考文献：
  名称：

  Unprecedented Regio- and Stereoselective Conversion of 1-Cyclopropyl-3-ethoxycyclopentadienes to 3-(E)-Alkylidenecyclopentenes

  摘要：

  Cyclopropylalkynes 1 were converted into cyclopropyl-substituted 3-ethoxy-5-dimethylaminocyclopentadienes 4 via initially formed (beta-dimethylaminoethenyl)carbene complexes 3 and their subsequent-formal [3 + 2] cycloaddition to a second alkyne of type 1 (overall yields 51-59%). New regio- and stereoselective 1,7-addition and 1,6-substitution reactions have been developed that convert cyclopentadienes 4 into highly functionalized cyclopentenes 5 and 11, respectively (yields 98-99% and 61%, respectively). An in situ domino reaction consisting of a [3 + 2] cycloaddition and subsequent 1,7-addition has also been achieved (86% overall yield).

  DOI：

  10.1021/jo980938z

文献信息

• Unprecedented Regio- and Stereoselective Conversion of 1-Cyclopropyl-3-ethoxycyclopentadienes to 3-(<i>E</i>)-Alkylidenecyclopentenes
  作者：Bernard L. Flynn、Armin de Meijere

  DOI：10.1021/jo980938z

  日期：1999.1.1

  Cyclopropylalkynes 1 were converted into cyclopropyl-substituted 3-ethoxy-5-dimethylaminocyclopentadienes 4 via initially formed (beta-dimethylaminoethenyl)carbene complexes 3 and their subsequent-formal [3 + 2] cycloaddition to a second alkyne of type 1 (overall yields 51-59%). New regio- and stereoselective 1,7-addition and 1,6-substitution reactions have been developed that convert cyclopentadienes 4 into highly functionalized cyclopentenes 5 and 11, respectively (yields 98-99% and 61%, respectively). An in situ domino reaction consisting of a [3 + 2] cycloaddition and subsequent 1,7-addition has also been achieved (86% overall yield).