4-Fluor-2-cyclohexyl-phenol | 1510-42-5

• 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-Fluor-2-cyclohexyl-phenol
• 英文别名: 2-Cyclohexyl-4-fluorophenol
• CAS: 1510-42-5
• 化学式: C₁₂H₁₅FO
• 分子量: 194.249
• InChiKey: LNQUVVANFJYEJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Fluor-2-cyclohexyl-phenol 在 吡啶 、 1,1'-双(二苯基膦)二茂铁 、 草酰氯 、 2-碘联苯 、 potassium acetate 、 palladium diacetate 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 5.25h， 生成 6'-fluoro-2'-methoxyspiro[cyclohexane-1,1'-isoindolin]-3'-one
  参考文献：
  名称：

  Iodoarene-Catalyzed Stereospecific Intramolecular sp³ C–H Amination: Reaction Development and Mechanistic Insights

  摘要：

  A new strategy is reported for intramolecular Sp(3) C-H amination :under mild reaction conditions using iodoarene as catalyst and m-CPBA as oxidant. This C-H functionalization involving iodine(III) reagents generated in situ occurs readily at sterically hindered tertiary C-H bonds. DFT (M06-2X) calculations show that the preferred pathway involves an iodonium cation intermediate and proceeds via an energetically concerted transition state, through hydride transfer followed by the spontaneous C-N bond formation. ThiS leads to the experimentally observed amination at a chiral center without loss of stereo chemical information.

  DOI：

  10.1021/jacs.5b03488
• 作为产物：
  描述：

  4-氟苯酚 、 环己醇 在 磷酸 作用下， 反应 16.0h， 以31%的产率得到4-Fluor-2-cyclohexyl-phenol
  参考文献：
  名称：

  Iodoarene-Catalyzed Stereospecific Intramolecular sp³ C–H Amination: Reaction Development and Mechanistic Insights

  摘要：

  A new strategy is reported for intramolecular Sp(3) C-H amination :under mild reaction conditions using iodoarene as catalyst and m-CPBA as oxidant. This C-H functionalization involving iodine(III) reagents generated in situ occurs readily at sterically hindered tertiary C-H bonds. DFT (M06-2X) calculations show that the preferred pathway involves an iodonium cation intermediate and proceeds via an energetically concerted transition state, through hydride transfer followed by the spontaneous C-N bond formation. ThiS leads to the experimentally observed amination at a chiral center without loss of stereo chemical information.

  DOI：

  10.1021/jacs.5b03488

文献信息

• Catalytic Asymmetric Hydroalkenylation of Vinylarenes: Electronic Effects of Substrates and Chiral N-Heterocyclic Carbene Ligands
  作者：Chun-Yu Ho、Chun-Wa Chan、Lisi He

  DOI：10.1002/anie.201411882

  日期：2015.4.7

  An asymmetric tail‐to‐tail cross‐hydroalkenylation of vinylarenes with terminal olefins was achieved by catalysis with NiH complexes bearing chiral N‐heterocyclic carbenes (NHCs). The reaction provides branched gem‐disubstituted olefins with high enantioselectivity (up to 94 % ee) and chemoselectivity (cross/homo product ratio: up to 99:1). Electronic effects of the substituents on the vinylarenes and

  乙烯基芳烃与末端烯烃的不对称尾到尾交叉氢化烯基化反应是通过催化带有手性N-杂环卡宾（NHC）的NiH配合物实现的。该反应提供了具有高对映选择性（最高94％ee）和化学选择性（交叉/均产物比：最高99：1）的支链宝石-二取代烯烃 。NHC配体的乙烯基芳烃和N-芳基上的取代基的电子效应（但不是π，π堆积机制）有助于空间效应并影响交叉氢化烯基化的结果。
• 2-Cycloalkyl phenoxyacetic acid CRTh2 receptor antagonists
  作者：David A. Sandham、Clive Aldcroft、Urs Baettig、Lucy Barker、David Beer、Gurdip Bhalay、Zarin Brown、Gerald Dubois、David Budd、Louise Bidlake、Emma Campbell、Brian Cox、Brian Everatt、David Harrison、Catherine J. Leblanc、Jodie Manini、Rachael Profit、Rowan Stringer、Katy S. Thompson、Katharine L. Turner、Morris F. Tweed、Christoph Walker、Simon J. Watson、Steven Whitebread、Jennifer Willis、Gareth Williams、Caroline Wilson

  DOI：10.1016/j.bmcl.2007.05.019

  日期：2007.8

  High throughput screening identified a phenoxyacetic acid scaffold as a novel CRTh2 receptor antagonist chemotype, which could be optimised to furnish a compound with functional potency for inhibition of human eosinophil shape change and oral bioavailability in the rat. (c) 2007 Elsevier Ltd. All rights reserved.