2,2',3,3'-四羟基-1,1'-联萘 | 39215-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,2',3,3'-四羟基-1,1'-联萘
• 英文名称: rac-2,2',3,3'-tetrahydroxy-1,1'-binaphthyl
• 英文别名: 2,2',3,3'-tetrahydroxy-1,1'-binaphthalene；2,2',3,3'-Tetrahydroxy-dinaphthyl-(1,1')；2,2',3,3'-tetrahydroxy-1,1'-dinaphthyl；[1,1'-binaphthalene]-2,2',3,3'-tetraol；2,2'3,3'-tetrahydroxy-1,1'-binaphthyl；2,3,2'3'-tetrahydroxy-1,1'binaphthyl；1-(2,3-dihydroxynaphthalen-1-yl)naphthalene-2,3-diol
• CAS: 39215-21-9；63323-58-0
• 化学式: C₂₀H₁₄O₄
• mdl: MFCD00188003
• 分子量: 318.329
• InChiKey: OOSHJGKXQBJASF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 海关编码：
  2907299090

反应信息

• 作为反应物：
  描述：

  2,2',3,3'-四羟基-1,1'-联萘 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以62%的产率得到4,4'-Dibromo-[1,1']binaphthalenyl-2,3,2',3'-tetraol
  参考文献：
  名称：

  Reaction of 1,4-Dibromo-2,3-dihydroxynaphthalene with 2-Naphthoxide Ion. Solvent and Cation Control in the Formation of the Conformationally Locked Stereoisomers of 2,2‘,3‘,2‘‘-Tetrahydroxy-1,1‘:4‘,1‘‘-ternaphthyl and 2,2‘,3‘,2‘‘,3‘‘,2‘‘‘-Hexahydroxy-1,1‘:4‘,1‘‘:4‘‘,1‘‘‘-quaternaphthyl

  摘要：

  The reaction of the dibromide 1 with the 2-naphthoxide ion 2 proceeds under remarkably mild conditions (25-50 degrees C), yielding all possible stereoisomers of ternaphthol 3 and quaternaphthol 4. An unambiguous structure assignment has been made for the individual stereoisomers and conditions for their thermal interconversion have been established. In contrast to a nonselective distribution of stereoisomers found in the thermodynamic equilibrium mixture, a high stereoselectivity can be induced in the coupling reaction under kinetic control. The coordinating ability of the alkali metal counterion (M(+)) of the participating 2-naphthoxide ion 2 has been found to play a key role in the stereocontrol, supporting strongly the formation of the cis stereoisomers of 3 and 4. When the coordinating ability of M(+) is suppressed by an efficient solvation and/or by complexation with 18-crown-6, formation of the traits stereoisomers prevails in the reaction.

  DOI：

  10.1021/jo951632k
• 作为产物：
  描述：

  2,3-二羟基萘 在 3-甲基苯噻吩 、 双氧水 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以50%的产率得到2,2',3,3'-四羟基-1,1'-联萘
  参考文献：
  名称：

  亚砜催化的2-萘酚氧化偶联中的Pummerer反应中断

  摘要：

  通过H 2 O 2硫氧化原位生成的苯并噻吩S-氧化物催化剂介导2-萘酚的氧化偶联。催化过程的关键是使用不寻常的苯并噻吩S-氧化物中断的Pummerer反应，然后与第二个配偶偶合，捕获和转化2-萘酚配偶的反应性。新的催化歧管已在生物活性天然产物（±）-尼莫酮和（±）-异麦酮的合成中得到展示。尽管Pummerer反应被广泛使用，但它们在催化中的应用却很少，我们的方法代表了一种新的无金属C-C键形成的催化流形。

  DOI：

  10.1002/anie.201903492
• 作为试剂：
  描述：

  水杨醛 在 奎宁环 、 2,2',3,3'-四羟基-1,1'-联萘 、 BF₄^(1-)*C₁₈H₁₇F₅N₃O⁽¹⁺⁾ 作用下， 以 甲苯 为溶剂， 生成 methyl (2R)-2-(2-methoxy-2-oxoethyl)-3-oxo-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes

  摘要：

  我们报道了一种多催化剂、一锅法、不对称的Michael/Stetter反应，用于将水杨醛和电子不足的炔烃进行级联反应。该反应级联进行，首先通过胺介导的Michael加成，然后通过一种N-杂环卡宾促进的分子内Stetter反应。多种水杨醛、双重活化的炔烃和末端亲电性烯烃参与了一步或两步的反应，产率中等至良好，对映选择性良好至优异，得到了多种苯并呋喃酮产物。还探讨了反应对映选择性的起源；反应中间体的E/Z几何构型以及催化量的邻苯二酚添加剂的存在被发现会影响反应的对映选择性。

  DOI：

  10.1073/pnas.1002830107

文献信息

• Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
  作者：Nagnath Yadav More、Masilamani Jeganmohan

  DOI：10.1039/c7cc04829g

  日期：——

  A regioselective synthesis of unsymmetrical and symmetrical biphenols and binaphthols via oxidative coupling of phenols or naphthols in the presence of K2S2O8 in CF3COOH at ambient conditions is described. Interestingly, 1:1 ratio of H2O and CH3CN solvent mixtures at 80 °C instead of CF3COOH provided substituted unsymmetrical quinones. A gram scale synthesis of biphenols and binaphthols was demonstrated

  描述了在环境条件下在CF 3 COOH中在K 2 S 2 O 8存在下通过酚或萘酚的氧化偶联的不对称和对称的双酚和联萘酚的区域选择性合成。有趣的是，在80°C的H2O和CH3CN溶剂混合物以1：1的比例代替CF3COOH提供了取代的不对称醌。证明了双酚和联萘酚的克级合成。
• Synthesis of Phenol, Aromatic Ether, and Benzofuran Derivatives by Copper-Catalyzed Hydroxylation of Aryl Halides
  作者：Dongbing Zhao、Ningjie Wu、Shuai Zhang、Peihua Xi、Xiaoyu Su、Jingbo Lan、Jingsong You

  DOI：10.1002/anie.200903923

  日期：2009.11.2

  A smooth operator: The copper‐catalyzed synthesis of phenols from aryl halides was carried out under relatively mild reaction conditions. Alkyl aryl ethers and benzofurans could also be prepared smoothly by one‐pot domino protocols based on hydroxylation of aryl iodides (see scheme).

  平稳的操作员：在相对温和的反应条件下，铜从芳基卤化物中催化合成苯酚。烷基芳基醚和苯并呋喃也可通过基于芳基碘化物羟基化的一锅多米诺协议顺利制备（参见方案）。
• TLC plates as a convenient platform for solvent-free reactions
  作者：Jonathan M. Stoddard、Lien Nguyen、Hector Mata-Chavez、Kelly Nguyen

  DOI：10.1039/b616311d

  日期：——

  Solvent-free oxidative couplings of naphthols have been optimized by co-spotting catalysts and substrates directly on silica TLC plates and heating, followed by chromatography, staining, and qualitative visualization.

  无溶剂的萘酚氧化偶联反应通过将催化剂和底物直接共点在硅胶薄层色谱板上并加热，随后进行色谱、染色和定性可视化进行了优化。
• Intense excimer CPL of pyrenes linked to a quaternaphthyl
  作者：Kazuto Takaishi、Ryosuke Takehana、Tadashi Ema

  DOI：10.1039/c7cc09187g

  日期：——

  (R,R,R)-Quaternaphthyl possessing multiple pyrenes emits CPL with high Φ_FL and g_lum values both in solution and in the solid state.

  具有多个芘基团的（R，R，R）-四芘基在溶液和固态中发射高ΦFL和glum值的环形偏振荧光。
• [EN] LADDER POLYMERS WITH INTRINSIC MICROPOROSITY AND PROCESS FOR PRODUCTION THEREOF<br/>[FR] POLYMÈRES ÉCHELLE DOTÉS D'UNE MICROPOROSITÉ INTRINSÈQUE ET LEUR PROCÉDÉ DE PRODUCTION
  申请人：CA NAT RESEARCH COUNCIL

  公开号：WO2010048694A1

  公开（公告）日：2010-05-06

  A polymer of formula (I): where: n is an integer from 10 to 5,000; m is an integer from 10 to 5,000; Ar1 and Ar3 are the same or different and are residues derived from a tetra-hydroxy aromatic monomer, the tetra-hydroxy aromatic monomer being wherein R is the same or different and is H or a C1-C8 alkyl, C2-C8 alkenyl or C3-C8 cycloalkyl group; and, Ar2 and Ar4 are the same or different and are residues derived from a tetra-halogenated aromatic monomer, the tetra-halogenated aromatic monomer being wherein X is F, Cl or Br, and R1 and R2 are the same or different and are wherein y is an integer from 1 to 8; with the proviso that when Ar1 is the same as Ar3 and Ar2 is the same as Ar4, R1 and R2 are not both -CN is useful as a material for gas separation, vapor separation, adsorbents or catalysis.

  一种化学式（I）的聚合物：其中：n为10至5,000之间的整数；m为10至5,000之间的整数；Ar1和Ar3相同或不同，是来自四羟基芳香单体的残基，四羟基芳香单体是其中R相同或不同，为H或C1-C8烷基，C2-C8烯基或C3-C8环烷基；Ar2和Ar4相同或不同，是来自四卤代芳香单体的残基，四卤代芳香单体是其中X为F、Cl或Br，且R1和R2相同或不同，其中y为1至8之间的整数；但当Ar1与Ar3相同时，Ar2与Ar4相同，R1和R2不同时为-CN时，可用作气体分离、蒸汽分离、吸附剂或催化剂的材料。