4-fluorophenyl(2-naphthyl)methanol | 147022-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-fluorophenyl(2-naphthyl)methanol
• 英文别名: (4-fluorophenyl)(naphthalen-2-yl)methanol；(4-Fluorophenyl)-naphthalen-2-ylmethanol
• CAS: 147022-25-1
• 化学式: C₁₇H₁₃FO
• 分子量: 252.288
• InChiKey: YSHJRRISIWWJNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-fluorophenyl(2-naphthyl)methanol 在 NiBr2*diglyme 、 silver fluoride 、 sodium hydride 、 三环己基膦 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 7.0h， 生成 ((4-fluorophenyl)(naphthalen-2-yl)methyl)trimethylsilane
  参考文献：
  名称：

  Nickel-Mediated Enantiospecific Silylation via Benzylic C–OMe Bond Cleavage

  摘要：

  DOI：

  10.1021/acs.orglett.0c04316
• 作为产物：
  描述：

  2-(4-fluorobenzoyl)naphthalene 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以96%的产率得到4-fluorophenyl(2-naphthyl)methanol
  参考文献：
  名称：

  Research on antibacterial and antifungal agents. 16. Synthesis and antifungal activities of 1-[α-(1-naphthyl)benzyl]imidazole derivatives and related 2-naphthyl isomers

  摘要：

  Some 1-arylmethylimidazoles bearing a naphthyl group at the a position of benzyl moiety have been synthesized and tested as antifungal agents against Candida albicans and Candida spp. Such derivatives resemble bifonazole and naftifine, two important antimycotic agents of clinical use. Various compounds were found highly active when tested against Candida strains in comparison with bifonazole, miconazole, clotrimazole and ketoconazole.

  DOI：

  10.1016/0223-5234(92)90089-j

文献信息

• Bulky <i>N</i> ‐Heterocyclic‐Carbene‐Coordinated Palladium Catalysts for 1,2‐Addition of Arylboron Compounds to Carbonyl Compounds
  作者：Yuta Okuda、Masahiro Nagaoka、Tetsuya Yamamoto

  DOI：10.1002/cctc.202001464

  日期：2020.12.16

  primary, secondary, and tertiary alcohols by the 1,2‐addition of arylboronic acids or boronates to carbonyl compounds, including unactivated ketones, using novel bulky yet flexible N‐heterocyclic carbene (NHC)‐coordinated 2,6‐di(pentan‐3‐yl)aniline (IPent)‐based cyclometallated palladium complexes (CYPs) as catalysts is reported. The PhS‐IPent‐CYP‐catalyzed reactions are efficient at low catalyst loadings

  使用新型但又灵活的N杂环卡宾（NHC）配位的2,6-di（据报道以戊烷-3-基）苯胺（IPent）为基的环金属化钯配合物（CYPs）。PhS-IPent-CYP催化的反应在低催化剂负载量（0.02-0.3 mol％Pd）下有效，而1,2-加成的出色催化活性归因于NHC配体的空间体积。这些反应可产生各种功能化的苄醇，这些化合物很难通过经典方案使用高活性有机镁或锂试剂进行合成。
• Addition reaction of arylboronic acids to aldehydes and α,β-unsaturated carbonyl compounds catalyzed by conventional palladium complexes in the presence of chloroform
  作者：Tetsuya Yamamoto、Michiko Iizuka、Hiroto Takenaka、Tetsuo Ohta、Yoshihiko Ito

  DOI：10.1016/j.jorganchem.2008.12.032

  日期：2009.4

  Arylboronic acids react with aldehydes and α,β-unsaturated carbonyl compounds in the presence of a base and a catalytic amount of a palladium(0) complex with chloroform, affording the corresponding addition products in good yields, and chiral benzhydrol was obtained with up to 43% e.e. using (S,S)-bppm as a ligand. General palladium complexes have no catalytic activity without chloroform. Because chloroform

  芳基硼酸在碱和催化量的钯（0）与氯仿的存在下，与醛和α，β-不饱和羰基化合物反应，以高收率提供相应的加成产物，并获得了最高使用（S，S）-bppm作为配体的ee为43％。普通的钯配合物没有氯仿就没有催化活性。因为氯仿对于该反应是必不可少的，所以二氯甲基钯（II）会促进这些反应。
• Rhodium-catalyzed benzylic fluorination of trichloroacetimidates
  作者：Qi Zhang、Jason C. Mixdorf、Gilbert J. Reynders、Hien M. Nguyen

  DOI：10.1016/j.tet.2015.04.066

  日期：2015.9

  via rhodium-catalyzed nucleophilic fluorination of benzylic trichloroacetimidates. A variety of naphthyl, phenyl, and pyridinyl trichloroacetimidates were fluorinated with Et3N·3HF reagent to provide fluorine-containing compounds in moderate to high yields under mild and operationally simple conditions. Preliminary mechanistic studies suggest that benzylic fluorination of trichloroacetimidate substrates

  通过铑催化的苄基三氯乙亚氨酸酯的亲核氟化反应合成了氟化苯甲酸酯。用Et 3 N·3HF试剂对各种萘基，苯基和吡啶基三氯乙酰亚胺酸酯进行氟化，以中等和高收率在温和且操作简单的条件下提供含氟化合物。初步的机理研究表明，三氯乙酰亚氨酸酯底物的苄基氟化反应更可能通过铑催化剂生成的离散的苄基阳离子进行。
• Palladium-catalyzed arylation of aldehydes with bromo-substituted 1,3-diaryl-imidazoline carbene ligand
  作者：Tetsuya Yamamoto、Takuma Furusawa、Azamat Zhumagazin、Tetsu Yamakawa、Yohei Oe、Tetsuo Ohta

  DOI：10.1016/j.tet.2014.11.051

  日期：2015.1

  The combination of 0 valent palladium precursor and bromo-substituted 1,3-diaryl-imidazoline carbene ligand precursor such as 1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-imidazolinium chloride 1a exhibited high catalytic activity for the 1,2-addition of arylboronic acids to aldehydes including aqueous formaldehyde. (C) 2014 Elsevier Ltd. All rights reserved.
• Palladium-imidazolinium carbene-catalyzed arylation of aldehydes with arylboronic acids in water
  作者：Masami Kuriyama、Natsuki Ishiyama、Rumiko Shimazawa、Osamu Onomura

  DOI：10.1016/j.tet.2010.06.049

  日期：2010.8

  The catalytic arylation of aldehydes with arylboronic acids in only water was found to be achieved using the palladium/thioether-imidazolinium chloride system in good to excellent yields. This catalytic process showed high tolerance for a broad range of substrates, giving a variety of carbinol derivatives with 2.0-3.0 mol % of the catalyst. (C) 2010 Elsevier Ltd. All rights reserved.