1-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)prop-2-en-1-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: 1-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)prop-2-en-1-ol
• 英文别名: 1-[4-[[3-[4-(Trifluoromethyl)phenyl]phenyl]methoxy]phenyl]prop-2-en-1-ol；1-[4-[[3-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]prop-2-en-1-ol
• 化学式: C₂₃H₁₉F₃O₂
• 分子量: 384.398
• InChiKey: MUTJWBNHUNXYDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)prop-2-en-1-ol 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 potassium hydrogen bifluoride 、 5-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-5H-dibenzo[b,f]azepine 、 四丁基溴化铵 、 9-硼双环[3.3.1]壬烷 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-yn-1-ol
  参考文献：
  名称：

  Iridium-Catalyzed Enantioselective Allylic Alkynylation

  摘要：

  No leaving group needed: With an Ir(P,olefin) complex as catalyst, the direct enantioselective allylic alkynylation of secondary allylic alcohols with potassium alkynyltrifluoroborates as alkynylating reagents has been achieved. High levels of enantioselectivity and high yields were achieved with this operationally easy and robust protocol, the use of which was demonstrated in the synthesis of GPR40 receptor agonist AMG 837. cod = 1,5-cyclooctadiene.

  DOI：

  10.1002/anie.201302731
• 作为产物：
  描述：

  3-(bromomethyl)-4'-(trifluoromethyl)-1,1'-biphenyl 、 乙烯基氯化镁 、 对羟基苯甲醛 在 potassium carbonate 、 水 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 反应 25.5h， 以80%的产率得到1-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)prop-2-en-1-ol
  参考文献：
  名称：

  Iridium-Catalyzed Enantioselective Allylic Alkynylation

  摘要：

  No leaving group needed: With an Ir(P,olefin) complex as catalyst, the direct enantioselective allylic alkynylation of secondary allylic alcohols with potassium alkynyltrifluoroborates as alkynylating reagents has been achieved. High levels of enantioselectivity and high yields were achieved with this operationally easy and robust protocol, the use of which was demonstrated in the synthesis of GPR40 receptor agonist AMG 837. cod = 1,5-cyclooctadiene.

  DOI：

  10.1002/anie.201302731

文献信息

• Iridium-Catalyzed Enantioselective Allylic Alkynylation
  作者：James Y. Hamilton、David Sarlah、Erick M. Carreira

  DOI：10.1002/anie.201302731

  日期：2013.7.15

  No leaving group needed: With an Ir(P,olefin) complex as catalyst, the direct enantioselective allylic alkynylation of secondary allylic alcohols with potassium alkynyltrifluoroborates as alkynylating reagents has been achieved. High levels of enantioselectivity and high yields were achieved with this operationally easy and robust protocol, the use of which was demonstrated in the synthesis of GPR40 receptor agonist AMG 837. cod = 1,5-cyclooctadiene.