(4-chlorophenyl)(naphthalene-2-yl)methanol | 147022-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4-chlorophenyl)(naphthalene-2-yl)methanol
• 英文别名: (4-chlorophenyl)(naphthalen-2-yl)methanol；'；(4-Chlorophenyl)-naphthalen-2-ylmethanol
• CAS: 147022-24-0
• 化学式: C₁₇H₁₃ClO
• 分子量: 268.743
• InChiKey: SSKZUGRPCFXHOE-UHFFFAOYSA-N

物化性质

• 沸点：
  447.2±30.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  1

反应信息

• 作为反应物：
  描述：

  (4-chlorophenyl)(naphthalene-2-yl)methanol 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 生成 2-(4-chlorobenzyl)naphthalene
  参考文献：
  名称：

  757.芳核的烷基化。第十四部分。萘

  摘要：

  DOI：

  10.1039/jr9650004101
• 作为产物：
  描述：

  (4-氯苯基)-萘-2-基甲酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以97%的产率得到(4-chlorophenyl)(naphthalene-2-yl)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。
• 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。
• Mechanochemistry‐Amended Barbier Reaction as an Expedient Alternative to Grignard Synthesis**
  作者：Jagadeesh Varma Nallaparaju、Tatsiana Nikonovich、Tatsiana Jarg、Danylo Merzhyievskyi、Riina Aav、Dzmitry G. Kananovich

  DOI：10.1002/anie.202305775

  日期：2023.9.25

  Use of mechanochemistry enabled the rapid in situ generation of Grignard reagents, thereby overcoming the longstanding limitations of the Magnesium-mediated Barbier reaction in solution.

  机械化学的使用使得格氏试剂能够快速原位生成，从而克服了溶液中镁介导的巴比尔反应的长期限制。
• 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.
• Synthesis of Triarylmethanes by Palladium-Catalyzed C–H/C–O Coupling of Oxazoles and Diarylmethanol Derivatives
  作者：Sho Tabuchi、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo5010636

  日期：2014.6.20

  A PdCl2(MeCN)2/PPhCy2 catalyst couples oxazoles with diarylmethyl carbonates or pivalates to form the corresponding triarylmethanes in good yields. The catalysis involves successive secondary benzylic sp(3) C-O and heteroaromatic sp(2) C-H cleavages and provides an effective access to heteroarene-containing triarylmethanes from nonhalogenated and nonmetalated starting materials, which is complementary to precedented cross-coupling technologies with organic halides and organometallic reagents.