2-(4'-bromo-biphenyl-4-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol

• 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: 2-(4'-bromo-biphenyl-4-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol
• 英文别名: 2-[4-(4-Bromophenyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol；2-[4-(4-bromophenyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol
• 化学式: C₁₅H₉BrF₆O
• 分子量: 399.13
• InChiKey: HDNOJEJFNOGATC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,4'-二溴联苯 、 六氟丙酮 在 tri-n-butyllithium magnesate complex 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以59%的产率得到2-(4'-bromo-biphenyl-4-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol
  参考文献：
  名称：

  Selective metal-halogen exchange of 4,4′-dibromobiphenyl mediated by lithium tributylmagnesiate

  摘要：

  A selective metal-halogen exchange/electrophilic quench protocol on 4.4'-dibromobiphenyl 4 that proceeds under non-cryogenic 0 conditions is reported. This method provides an economic alternative to traditional transition-metal catalyzed cross-coupling chemistry to prepare various biaryls 7a-g. This novel route to functionalized biaryls was used as the basis for the kg-scale preparation of a biphenyl ketone 1, a key intermediate in the synthesis of a potent cathepsin K inhibitor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.039

文献信息

• Selective metal-halogen exchange of 4,4′-dibromobiphenyl mediated by lithium tributylmagnesiate
  作者：Sarah J. Dolman、Francis Gosselin、Paul D. O'Shea、Ian W. Davies

  DOI：10.1016/j.tet.2006.03.039

  日期：2006.5

  A selective metal-halogen exchange/electrophilic quench protocol on 4.4'-dibromobiphenyl 4 that proceeds under non-cryogenic 0 conditions is reported. This method provides an economic alternative to traditional transition-metal catalyzed cross-coupling chemistry to prepare various biaryls 7a-g. This novel route to functionalized biaryls was used as the basis for the kg-scale preparation of a biphenyl ketone 1, a key intermediate in the synthesis of a potent cathepsin K inhibitor. (c) 2006 Elsevier Ltd. All rights reserved.