3,3'-diethynyl-2,2'-dihydroxy-1,1'-binaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,3'-diethynyl-2,2'-dihydroxy-1,1'-binaphthalene
• 英文别名: (R)-3,3'-diethynyl-2,2'-dihydroxy-1,1'-binaphthyl；(R)-3,3'-diethynyl-1,1'-bi-2-naphthol；3-Ethynyl-1-(3-ethynyl-2-hydroxynaphthalen-1-yl)naphthalen-2-ol
• 化学式: C₂₄H₁₄O₂
• 分子量: 334.374
• InChiKey: WEFKGAJJPBPALV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• 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：

  3,3'-diethynyl-2,2'-dihydroxy-1,1'-binaphthalene 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 22.0h， 生成 (R)-3,3'-bis(2-iodophenylethynyl)-2,2'-dimethoxy-1,1'-binaphthyl
  参考文献：
  名称：

  Asymmetric synthesis of macrocyclic binaphthol dimers using a Sonogashira coupling reaction

  摘要：

  Asymmetric synthesis of 24- and 26-membered macrocyclic binaphthol dimers was achieved by assembling a 3,3'-diethynyl-1,1'-bi-2-naphthoI unit and 1,2- and 1,3-phenylene units with Sonogashira coupling reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.038
• 作为产物：
  描述：

  (R)-3,3'-di[(trimethylsilyl)ethynyl]-2,2'-dihydroxy-1,1'-binaphthyl 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以99%的产率得到3,3'-diethynyl-2,2'-dihydroxy-1,1'-binaphthalene
  参考文献：
  名称：

  醌类BINOL型化合物作为一类新的手性配体

  摘要：

  据报道，利用铬模板化的[3 + 2 + 1]苯并环化反应作为关键步骤，短而有效地合成了新型的醌取代的BINOL型配体。

  DOI：

  10.1016/j.tetasy.2005.08.026

文献信息

• Design and synthesis of new alkyl‐based chiral phosphoric acid catalysts
  作者：Xiaoxue Tang、Hualing He、Xiantao Fang、Zexu Chang、Jon C. Antilla

  DOI：10.1002/chir.23101

  日期：2019.8

  Using chiral BINOL‐derived phosphoric acids (PA's) to activate substrates for enhanced reactivity is now regarded as a powerful strategy to control enantioselectivity in asymmetric synthesis. Generally, most substituents at the 3,3′‐positions of BINOL PA's are aryl derivatives. These derivatives are pivotal in attaining high selectivity. PA's with alkyl substituents in these positions have rarely been

  现在，使用手性BINOL衍生的磷酸（PA's）活化底物以增强反应性被认为是控制不对称合成中对映选择性的有效策略。通常，BINOL PA的3,3'-位上的大多数取代基是芳基衍生物。这些衍生物对于获得高选择性至关重要。在这些位置带有烷基取代基的PA鲜有报道。在这里，我们在PA的3,3'位置引入了基于烷基的取代基。如果将这些新的潜在催化剂应用于反应中，将来可能会与手性PA催化化学中使用的底物发生改变的非共价相互作用（与这些位置的典型芳基取代基相反）。
• Dendritic, 1,1′-Binaphthalene-Derived Cleft-Type Receptors (Dendroclefts) for the Molecular Recognition of Pyranosides
  作者：Anja Bähr、Béatrice Felber、Katharina Schneider、François Diederich

  DOI：10.1002/1522-2675(20000705)83:7<1346::aid-hlca1346>3.0.co;2-3

  日期：2000.7.5

  Two series of optically active, cleft-type dendritic receptors (dendroclefts) for carbohydrate recognition were prepared by attaching Frechet-type dendrons via ethynediyl linkers to a core consisting of one or two 1,1′-binaphthalene-2,2′-diyl phosphate moieties. Sugar substrates were expected to bind via bidentate ionic H-bonding of two OH groups to the phosphodiester core and, additionally, to undergo

  通过将 Frechet 型树突通过乙炔二基连接体连接到由一个或两个 1,1'-binaphthalene-2,2'-diyl phosphate 组成的核心上，制备了两个系列用于碳水化合物识别的光学活性裂隙型树突受体 (dendroclefts)部分。预计糖底物将通过两个 OH 基团的双齿离子 H 键与磷酸二酯核心结合，此外，与周围树枝状楔的芳香环发生范德华和 CH···π 相互作用。用单个联萘合成树突受体 G-1-(S)-1、G-2-(S)-2 和 G-3-(S)-3（图 1；Gx=树突生成）核心从 3,3'-二乙炔基化的 MOM 保护 (MOM=methoxymethyl) 1,1'-binaphthalene-2 开始，2'-二醇 (S)-13，第 1-3 代的 Frechet 型树突通过 Sonogashira 交叉偶联连接（方案 3）。MOM-醚脱保护，然后形成磷酸二酯和离子交换
• Synthesis of modified binol-phosphoramidites
  作者：Carl Recsei、Christopher S.P. McErlean

  DOI：10.1016/j.tet.2011.11.020

  日期：2012.1

  A number of chiral phosphoramidite ligands containing electronically different N-heterocycles at the 3,3'-positions of the binol scaffold were synthesized. The nucleophilicity of the pendant heterocycles correlated with the propensity of the P(III) centre to undergo aerobic oxidation to P(V). Due to an unexpected Staudinger-type reaction between the product phosphoramidites, the order in which the individual synthetic transformations were conducted was found to be important. The synthesis of a phosphoramidite ligand containing flanking groups at the 3,3'-positions of the binol scaffold in addition to a stereogenic phosphorus atom was also undertaken. (C) 2011 Elsevier Ltd. All rights reserved.
• Chiral Metallacyclophanes:  Self-Assembly, Characterization, and Application in Asymmetric Catalysis
  作者：Jiang Hua、Wenbin Lin

  DOI：10.1021/ol036111v

  日期：2004.3.1

  A family of chiral metallacyclophanes has been readily assembled based on robust Pt-acetylide linkage and characterized by a variety of spectroscopic techniques and X-ray crystallography. The steric congestion around the chiral dihydroxy groups in rigid metallacyclophane 4 prevents their reactions with Ti((OPr)-Pr-i)(4) to form active catalysts for enantioselective diethylzinc additions to aromatic aldehydes. In contrast, chiral dihydroxy groups in more flexible unclosed metallacyclophane 5 are effective ligands for enantioselective catalytic diethylzinc additions to aromatic aldehydes.
• Quinoid BINOL-type compounds as a novel class of chiral ligands
  作者：Ana Minatti、Karl Heinz Dötz

  DOI：10.1016/j.tetasy.2005.08.026

  日期：2005.10

  A short and efficient synthesis of a novel family of quinone-substituted BINOL-type ligands exploiting the chromium-templated [3+2+1]benzannulation reaction as the key step is reported.

  据报道，利用铬模板化的[3 + 2 + 1]苯并环化反应作为关键步骤，短而有效地合成了新型的醌取代的BINOL型配体。