1-(2-hydroxyphenyl)naphthalen-2-ol | 883972-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-hydroxyphenyl)naphthalen-2-ol
• CAS: 883972-56-3
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: NSHUOOBDQPJJGW-UHFFFAOYSA-N

物化性质

• 沸点：
  399.3±22.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)naphthalen-2-ol 、 乙酸酐 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2-acetoxynaphthalen-1-yl)phenyl acetate
  参考文献：
  名称：

  Synthesis of Unsymmetrical o-Biphenols and o-Binaphthols via Silicon-Tethered Pd-Catalyzed C−H Arylation

  摘要：

  A mild, practical, and efficient method for the synthesis of unsymmetrical o-biphenols (including o-phenol-naphthols and o-binaphthols) has been developed. Unsymmetrical bis-aryloxy silanes, which were readily prepared in a semi-one-pot fashion, underwent the Pd-catalyzed intramolecular arylation followed by a routine TBAF desilylation step to furnish valuable unsymmetrical biphenols without necessity of isolation of seven-membered intermediates. The excellent functional group tolerance allows for synthesis of a variety of functionalized o-biphenols and o-binaphthols from easily available staring materials.

  DOI：

  10.1021/ol100924n
• 作为产物：
  描述：

  1-溴-2-萘酚 在 四(三苯基膦)钯 、 三溴化硼 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 1-(2-hydroxyphenyl)naphthalen-2-ol
  参考文献：
  名称：

  路易斯酸介导的2,2'-双酚的亲电子氰化。

  摘要：

  报道了路易斯酸介导的具有三氟甲磺酰基（Tf）保护基的2,2'-双酚的亲电子氰化。用毒性较小的可商购的MeSCN作为氰化试剂进行氰化反应，可以中等至高收率得到一系列3-cyan-2,2'-双酚。三氟甲磺酰基（Tf）作为保护基的使用对于此转化成功至关重要。此外，氰化产物易于转化为各种合成有用的分子。该协议具有高效，出色的区域选择性和良好的官能团相容性的特点，可为合成和修饰生物活性化合物，催化剂和配体提供实用工具。

  DOI：

  10.1021/acs.joc.0c00458

文献信息

• METHOD FOR MANUFACTURING OPTICALLY ACTIVE MENTHOL
  申请人：Tsuda Toshiro

  公开号：US20130253228A1

  公开（公告）日：2013-09-26

  An object of the present invention is to provide a method for manufacturing an optically active menthol having fewer steps, which generates less environmentally polluting waste because a catalytic reaction is involved in all of the steps, and is capable of saving a production cost. The present invention relates to a method for manufacturing an optically active menthol, including the following steps: A-1) asymmetrically hydrogenating at least one of geranial and neral to thereby obtain an optically active citronellal, B-1) conducting a ring-closure reaction of the optically active citronellal in the presence of an acid catalyst to thereby obtain an optically active isopulegol, and C-1) hydrogenating the optically active isopulegol to thereby obtain an optically active menthol.

  本发明的目的是提供一种制造具有较少步骤的光学活性薄荷醇的方法，因为所有步骤都涉及催化反应，所以产生的环境污染废物较少，并且能够节省生产成本。本发明涉及一种制造光学活性薄荷醇的方法，包括以下步骤：A-1）不对称地氢化至少一种香叶醛和柠檬醛以获得光学活性柠檬醛，B-1）在酸催化剂存在下对光学活性柠檬醛进行环闭合反应，从而获得光学活性异薄荷醇，以及C-1）对光学活性异薄荷醇进行氢化以获得光学活性薄荷醇。
• Regioselective Construction of Functionalized Biarylols by Fe(OTf)₃ -Catalyzed Direct Arylation of 1-Diazonaphthalen-2(1<i>H</i> )-ones and Their Fluorescence Properties
  作者：Krishna Bahadur Somai Magar、T. N. J. I. Edison、Yong Rok Lee

  DOI：10.1002/ejoc.201701533

  日期：2017.12.22

  A facile and efficient protocol for the construction of functionalized biarylols by Fe(OTf)3-catalyzed direct arylation of 1-diazonaphthalen-2(1H)-ones with arenes has been developed. This methodology provides diverse 1-arylnaphthalen-2-ols in moderate to good yields. This approach has also been applied to the synthesis of biologically interesting polycyclic-aromatic-substituted and heteroaryl-substituted

  已经开发了一种通过 Fe(OTf)3 催化 1-diazonaphthalen-2(1H)-ones 与芳烃的直接芳基化来构建功能化联芳醇的简便有效的协议。这种方法以中等至良好的产率提供了多种 1-arylnaphthalen-2-ols。这种方法也已应用于合成具有生物学意义的多环芳烃取代和杂芳基取代 naphthalen-2-ols。带有蒽支架的合成化合物可用作克隆细胞共聚焦成像的潜在荧光生物标志物。
• [EN] ALUMINIUM COMPLEXES AND USE THEREOF AS A CATALYST IN INTRAMOLECULAR RING CLOSURE REACTIONS<br/>[FR] COMPLEXES D'ALUMINIUM ET LEUR UTILISATION EN TANT QUE CATALYSEUR DANS DES RÉACTIONS INTRAMOLÉCULAIRES DE FERMETURE DE CYCLE
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2010071227A1

  公开（公告）日：2010-06-24

  To provide a process for increasing the proportion of an optical isomer of not only a compound having a closed ring but also a compound not having a closed ring when an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule is subjected to a ring closing reaction. A process for increasing the proportion of an optical isomer characterized by subjecting an optical isomer mixture of a compound having both a formyl group and a double bond capable of causing a carbonyl-ene ring closing reaction in the same molecule to a ring closing reaction in the presence of a predetermined aluminum complex represented by the general formula: [Al2(L1)n(L2)3-n]m.

  提供一种增加光学异构体比例的过程，不仅适用于具有闭环的化合物，也适用于不具有闭环的化合物，当具有甲醛基和能够在同一分子中引起羰基-烯烃环闭合反应的双键的化合物的光学异构体混合物经过环闭合反应时。一种增加光学异构体比例的过程，其特征在于将具有甲醛基和能够在同一分子中引起羰基-烯烃环闭合反应的双键的化合物的光学异构体混合物在预定的铝配合物存在下进行环闭合反应，该铝配合物由通式表示：[AL2(L1)n(L2)3-n]m。
• ALUMINUM COMPLEX AND USE THEREOF
  申请人：Takasago International Corporation

  公开号：EP2279992A1

  公开（公告）日：2011-02-02

  Provided is a process in which cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, increases the ratio of a particular optical isomer not only in a cyclized compound, but also in an unreacted compound. The process comprises performing, in the presence of a specified aluminum complex represented by the general formula: [Al2(L1)n (L2)3-n]m, cyclization of a compound having, in a molecule, a formyl group and a double bond which allow carbonyl-ene cyclization, the compound existing as a mixture of optical isomers thereof, to increase the ratio of a particular optical isomer.

  提供的是一种过程，其中具有分子中的甲酰基和双键，可允许羰基-烯环化的化合物的环化，该化合物存在光学异构体混合物中，该过程不仅可以增加环化化合物中特定光学异构体的比例，还可以增加未反应化合物中特定光学异构体的比例。该过程包括在指定的铝络合物存在下进行，该铝络合物由一般式[AL2(L1)n(L2)3-n]m表示，对具有分子中的甲酰基和双键，可允许羰基-烯环化的化合物进行环化，该化合物存在光学异构体混合物中，以增加特定光学异构体的比例。
• ORGANOALUMINUM COMPOUND
  申请人：ITOH Hisanori

  公开号：US20110295031A1

  公开（公告）日：2011-12-01

  A catalyst for obtaining isopulegol of high diastereoselectivity by highly selective cyclization reaction of citronellal is provided. The present invention relates to an organoaluminum compound obtained by reacting at least one organoaluminumoxy compound selected from the group consisting of chain aluminoxanes, cyclic aluminoxanes and bis(dialkylaluminumoxy)alkylboranes, with at least one hydroxy compound selected from the group consisting of diarylphenols, bis(diarylphenol) compounds, biaryldiols, dimethanols and silanols.

  本发明提供了一种催化剂，用于通过高度选择性的环化反应从香茅醛中获得高对映选择性的异莰醇。本发明涉及通过将链状铝氧烷、环状铝氧烷和双(二烷基氧基)烷基硼烷等组中至少一种有机铝氧化合物与二苯基酚、双(二苯基酚)化合物、联苯二醇、二甲醇和硅烷等组中至少一种羟基化合物反应而得到的有机铝化合物。