(4E)-4-(2,2,3,3,4,4,5,5,5-nonafluoropentylidene)dec-2-yn-1-ol | 1187833-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4E)-4-(2,2,3,3,4,4,5,5,5-nonafluoropentylidene)dec-2-yn-1-ol
• CAS: 1187833-60-8
• 化学式: C₁₅H₁₇F₉O
• 分子量: 384.285
• InChiKey: XZQYZVKMWDFOFK-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4E)-4-(2,2,3,3,4,4,5,5,5-nonafluoropentylidene)dec-2-yn-1-ol 、 4-氟苯基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 以93%的产率得到4-(n-hexyl)-2-(4'-fluorophenyl)-6,7,7,8,8,9,9,9-octafluoronona-2,3,5(Z)-trienol
  参考文献：
  名称：

  Highly stereoselective synthesis of 6-perfluoroalkyl-6-fluoroalka-2,3,5-(Z)-trienols through carbometallation-elimination of 5-perfluoroalkyl-substituted 4(E)-alken-2-ynols with Grignard reagents

  摘要：

  A highly regio- and stereoselective sequential carbometallation and Z-selective beta-elimination reaction of 5-perfluoroalkyl-4(E)-en-2-ynols with Grignard reagents in Et2O has been developed to afford various 6-perfluoroalkyl-6-fluoroalka-2,3,5(Z)-trienols in good to excellent yields Primary or secondary alkyl or aryl Grignard reagents may be used to introduce the R-2 group to the 2-position of the starting materials referring to the hydroxyl group A mechanism for this transformation has been proposed. (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetlet.2009.09.003

文献信息

• Highly stereoselective synthesis of 6-perfluoroalkyl-6-fluoroalka-2,3,5-(Z)-trienols through carbometallation-elimination of 5-perfluoroalkyl-substituted 4(E)-alken-2-ynols with Grignard reagents
  作者：Zhichao Ma、Rong Zeng、Yihua Yu、Shengming Ma

  DOI：10.1016/j.tetlet.2009.09.003

  日期：2009.11

  A highly regio- and stereoselective sequential carbometallation and Z-selective beta-elimination reaction of 5-perfluoroalkyl-4(E)-en-2-ynols with Grignard reagents in Et2O has been developed to afford various 6-perfluoroalkyl-6-fluoroalka-2,3,5(Z)-trienols in good to excellent yields Primary or secondary alkyl or aryl Grignard reagents may be used to introduce the R-2 group to the 2-position of the starting materials referring to the hydroxyl group A mechanism for this transformation has been proposed. (C) 2009 Elsevier Ltd. All rights reserved