4-(3,5-bis(trifluoromethyl)phenyl)-1-(tetrahydrofuran-2-yl)butan-2-one | 1318571-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3,5-bis(trifluoromethyl)phenyl)-1-(tetrahydrofuran-2-yl)butan-2-one
• 英文别名: 4-[3,5-Bis(trifluoromethyl)phenyl]-1-(oxolan-2-yl)butan-2-one
• CAS: 1318571-51-5
• 化学式: C₁₆H₁₆F₆O₂
• 分子量: 354.292
• InChiKey: SYDLORRIITVVLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,5-双三氟甲基苯甲醛 在 二氯二茂钛 、 (2SR,4RS)-4-(tert-butyldiphenylsilyloxy)pyrrolidine-2-carboxylic acid 、 1-(3,5-bis(trifluoromethyl)phenyl)-3-(3-(dimethylamino)propyl) thiourea 、 三乙胺盐酸盐 、 锌 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 为溶剂， 反应 28.0h， 生成 4-(3,5-bis(trifluoromethyl)phenyl)-1-(tetrahydrofuran-2-yl)butan-2-one
  参考文献：
  名称：

  Thiourea/Proline Derivative-Catalyzed Synthesis of Tetrahydrofuran Derivatives: A Mechanistic View

  摘要：

  A thiourea/proline derivative-catalyzed synthesis of linear a-substituted tetrahydrofuran/pyran derivatives starting with lactol substrates is presented. This study demonstrates the utility and potential complications of using (thio)urea/proline cocatalysis as each of these catalysts is necessary to provide the observed reactivity, but a time-dependent decrease in enantioselectivity is observed. New mechanistic insights into (thio)urea/proline cocatalysis are presented.

  DOI：

  10.1021/jo200838v

文献信息

• Thiourea/Proline Derivative-Catalyzed Synthesis of Tetrahydrofuran Derivatives: A Mechanistic View
  作者：Suzanne M. Opalka、Jeremy L. Steinbacher、Brandon A. Lambiris、D. Tyler McQuade

  DOI：10.1021/jo200838v

  日期：2011.8.19

  A thiourea/proline derivative-catalyzed synthesis of linear a-substituted tetrahydrofuran/pyran derivatives starting with lactol substrates is presented. This study demonstrates the utility and potential complications of using (thio)urea/proline cocatalysis as each of these catalysts is necessary to provide the observed reactivity, but a time-dependent decrease in enantioselectivity is observed. New mechanistic insights into (thio)urea/proline cocatalysis are presented.