(1R,2S)-2-(4-fluorophenyl)-1,2-dihydronaphthalen-1-ol | 1092115-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-2-(4-fluorophenyl)-1,2-dihydronaphthalen-1-ol
• 英文别名: cis-2-(4'-fluorophenyl)-1,2-dihydronaphthalen-1-ol
• CAS: 1092115-05-3
• 化学式: C₁₆H₁₃FO
• 分子量: 240.277
• InChiKey: UEOXXZMLTOIIMZ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,4-epoxy-1,4-dihydronaphthalene 、 4-氟苯硼酸 在 (R)-(+)-5,5'-双[二(3,5-二甲苯基)膦]-4,4'-二-1,3-苯并二茂 、 dichloro( 1,5-cyclooctadiene)platinum(ll) 、 potassium fluoride 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 21.0h， 以75%的产率得到
  参考文献：
  名称：

  Platinum(II)-Catalyzed Asymmetric Ring-Opening Addition of Arylboronic Acids to Oxabenzonorbornadienes

  摘要：

  A new platinum(II)-catalyzed asymmetric ring-opening addition of arylboronic acids to oxabenzonorbornadienes was developed, which afforded the corresponding cis-2-aryl-1,2-dihydronaphthalen-1-ol products in high yields (up to 97%) with moderate to good enantioselectivities (up to 89% ee) under very mild conditions. The effects of various ligands, catalyst loading, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. The cis configuration of product 2m was confirmed by X-ray diffraction analysis. A potential mechanism for the present catalytic reaction is proposed.

  DOI：

  10.1021/jo402386k

文献信息

• Asymmetric Ring-Opening Reaction of Oxabicyclic Alkenes with Aryl Boronic Acids Catalyzed by P-Containing Palladacycles
  作者：Ting-Ke Zhang、Dong-Liang Mo、Li-Xin Dai、Xue-Long Hou

  DOI：10.1021/ol801294b

  日期：2008.9.1

  The chiral phosphine-containing palladacycle, synthesized easily from H-MOP, showed its high catalytic activity as well as asymmetric induction ability in ring-opening reaction of oxabicyclic alkenes with arylboronic acids, providing corresponding products in high yields and high ee.

  由H-MOP容易合成的含手性膦的palladacycle在氧杂双环烯烃与芳基硼酸的开环反应中显示出高催化活性和不对称诱导能力，从而以高收率和高ee提供相应的产物。