4-(4-chlorophenyl)-2-naphthol | 36159-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(4-chlorophenyl)-2-naphthol
• 英文别名: 4-(p-Chlor-phenyl)-2-naphthol；4-(4-Chlorophenyl)naphthalen-2-ol；4-(4-chlorophenyl)naphthalen-2-ol
• CAS: 36159-75-8
• 化学式: C₁₆H₁₁ClO
• 分子量: 254.716
• InChiKey: OPQFWYMPIIYELM-UHFFFAOYSA-N

物化性质

• 沸点：
  427.9±33.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-(4-chlorophenyl)-2-naphthol 在 氧气 、 2-苯乙胺 、 L-脯氨酸 、 copper dichloride 作用下， 以 乙醇 为溶剂， 反应 51.0h， 生成 (R)-(+)-4,4'-bis(4-chlorophenyl)-BINOL
  参考文献：
  名称：

  Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones

  摘要：

  The reaction of 2-(trimethylsilyl) phenyl triflate with aroylacetones in the presence of CsF gave the corresponding 4-aryl-2-naphthols. Substituted triflates also reacted with aroylacetones to afford 4-aryl-2-naphthols regioselectively. The enantioselective oxidation of 4aryl-2-naphthols with a chiral tridentate oxovanadium(IV) complex furnished the corresponding 4,4'-biaryl-1,1'-binaphthols in good yields.

  DOI：

  10.1055/s-0034-1380452
• 作为产物：
  描述：

  4-(4-chlorophenyl)naphthalen-2-yl dimethylcarbamate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以92%的产率得到4-(4-chlorophenyl)-2-naphthol
  参考文献：
  名称：

  钯（II）催化的O-β-氨基甲酸萘酯的亚选择性直接芳基化。

  摘要：

  使用Pd（OAc）2作为催化剂前体和K2S2O8和AgOAc作为氧化剂，可以完成O-β-氨基甲酸萘酯的选择性间芳基化反应。可以以中等到良好的产率引入一系列芳基硼酸。机理研究表明，氨基甲酸酯取代基具有独特的作用，并且该反应经历邻位羰基金属化/间位直接芳基化过程。

  DOI：

  10.1039/c4cc07997c

文献信息

• Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines
  作者：Tao-Yan Lin、Hai-Hong Wu、Jian-Jun Feng、Junliang Zhang

  DOI：10.1021/acs.orglett.7b01136

  日期：2017.6.2

  By taking advantage of chirality-transfer strategy, a chemo- and regioselective allylic alkylation of naphthols and phenols with vinylaziridines provides an atom-economic and efficient method for the synthesis of enantioenriched 2-vinyl-2-arylethylamine derivatives. Use of readily available starting materials, a broad substrate scope, high selectivity, mild reaction conditions, as well as versatile

  通过利用手性转移策略，萘酚和苯酚与乙烯基氮丙啶的化学和区域选择性烯丙基烷基化为合成对映体富集的2-乙烯基-2-芳基乙胺衍生物提供了一种原子经济有效的方法。使用容易获得的起始原料，广泛的底物范围，高选择性，温和的反应条件以及芳族乙胺产品的多功能官能化，使得该方法非常实用且有吸引力。
• Enantioselective Friedel–Crafts Alkylation Reactions of β‐Naphthols with Donor–Acceptor Aminocyclopropanes
  作者：Man Zhu、Dong‐Chao Wang、Ming‐Sheng Xie、Gui‐Rong Qu、Hai‐Ming Guo

  DOI：10.1002/chem.201804032

  日期：2018.10.17

  Friedel–Crafts alkylation reaction of β‐naphthols with donor–acceptor aminocyclopropane was developed. In the presence of a copper complex derived from Cu(OTf)2 and bisoxazoline, a series of γ‐substituted γ‐aminobutyric acid derivatives were obtained with good yields (up to 98 %) and excellent enantioselectivities (up to 98 %). Using this catalytic system, the 2‐amino cyclopropane‐1,1‐dicarboxylate was obtained

  开发了β-萘酚与供体-受体氨基环丙烷的对映选择性Friedel-Crafts烷基化反应。在衍生自Cu（OTf）2和双恶唑啉的铜络合物的存在下，获得了一系列γ-取代的γ-氨基丁酸衍生物，具有良好的收率（高达98％）和出色的对映选择性（高达98％）。使用该催化系统，通过有效的动力学拆分（s值高达90）获得了对映体过量很高（高达98％）的2-氨基环丙烷-1,1-二羧酸酯。Friedel-Crafts烷基化产物可以转化为四环1,3-恶嗪衍生物。
• Tandem carbon–carbon bond insertion and intramolecular aldol reaction of benzyne with aroylacetones: novel formation of 4,4′-disubstituted 1,1′-binaphthols
  作者：Kentaro Okuma、Ryoichi Itoyama、Ayumi Sou、Noriyoshi Nagahora、Kosei Shioj

  DOI：10.1039/c2cc36128k

  日期：——

  An efficient route to 4-aryl-2-naphthols from arynes and aroylacetones was developed by carbon-carbon bond insertion followed by an intramolecular aldol reaction and dehydration. Benzyne derived from 2-(trimethylsilyl)phenyl triflate reacted with benzoylacetones in refluxing acetonitrile to give 4-aryl-2-naphthols and 3-aryl-1-naphthols.

  通过碳-碳键插入，随后的分子内醛醇缩合反应和脱水，开发了从芳烃和芳酰基丙酮制备4-芳基-2-萘的有效途径。由2-（三甲基甲硅烷基）苯基三氟甲磺酸酯衍生的苯炔与苯甲酰基丙酮在回流的乙腈中反应，得到4-芳基-2-萘和3-芳基-1-萘。
• Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones
  作者：Kentaro Okuma、Kenta Horigami、Noriyoshi Nagahora、Kosei Shioji

  DOI：10.1055/s-0034-1380452

  日期：——

  The reaction of 2-(trimethylsilyl) phenyl triflate with aroylacetones in the presence of CsF gave the corresponding 4-aryl-2-naphthols. Substituted triflates also reacted with aroylacetones to afford 4-aryl-2-naphthols regioselectively. The enantioselective oxidation of 4aryl-2-naphthols with a chiral tridentate oxovanadium(IV) complex furnished the corresponding 4,4'-biaryl-1,1'-binaphthols in good yields.
• Palladium(<scp>ii</scp>)-catalyzed meta-selective direct arylation of O-β-naphthyl carbamate
  作者：Jingchang Zhang、Qingwen Liu、Xufei Liu、Suoqin Zhang、Pingping Jiang、Yanxiang Wang、Shengyuan Luo、Yang Li、Qifeng Wang

  DOI：10.1039/c4cc07997c

  日期：——

  could be introduced in moderate to good yields. Mechanistic investigation shows that the carbamate substituent has a unique effect and the reaction undergoes an ortho-carbometallation/meta-direct arylation process.

  使用Pd（OAc）2作为催化剂前体和K2S2O8和AgOAc作为氧化剂，可以完成O-β-氨基甲酸萘酯的选择性间芳基化反应。可以以中等到良好的产率引入一系列芳基硼酸。机理研究表明，氨基甲酸酯取代基具有独特的作用，并且该反应经历邻位羰基金属化/间位直接芳基化过程。