(S)-3,3'-diazidomethyl-2,2'-dimethoxymethoxy-1,1'-dinaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-3,3'-diazidomethyl-2,2'-dimethoxymethoxy-1,1'-dinaphthyl
• 英文别名: (S)-3,3'-bis(azidomethyl)-MOM-BINOL；3-(Azidomethyl)-1-[3-(azidomethyl)-2-(methoxymethoxy)naphthalen-1-yl]-2-(methoxymethoxy)naphthalene
• 化学式: C₂₆H₂₄N₆O₄
• 分子量: 484.514
• InChiKey: ANVPXHIGWOPSIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-3,3'-diazidomethyl-2,2'-dimethoxymethoxy-1,1'-dinaphthyl 在 copper(II) sulfate 、 sodium ascorbate 、 三氟乙酸 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 12,13,14,37,38,39-Hexazaundecacyclo[39.7.1.12,10.112,15.117,25.126,34.136,39.03,8.019,24.027,32.043,48]tetrapentaconta-1(49),2(54),3,5,7,9,13,15(53),17,19,21,23,25(52),26(51),27,29,31,33,36(50),37,41,43,45,47-tetracosaene-49,51,52,54-tetrol
  参考文献：
  名称：

  A novel BINOL-based cyclophane via click chemistry: synthesis and its applications for sensing silver ions

  摘要：

  A novel BINOL-based cyclophane 1 incorporating two triazole moieties was synthesized via click chemistry and characterized. Among the metal ions screened, only Ag+ was found to have the ability to quench the fluorescence of 1 in methanol solution. The 1:1 binding mode of 1-Ag+ was confirmed. The competitive experiment showed that compound 1 can be used as a specific fluorescent sensor for Ag+ over a wide range of competing cations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.050
• 作为产物：
  描述：

  (R)-2,2′-bis(methoxymethoxy)-[1,1′-binaphthalene]-3,3′-dicarbaldehyde 在 sodium tetrahydroborate 、 sodium azide 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 (S)-3,3'-diazidomethyl-2,2'-dimethoxymethoxy-1,1'-dinaphthyl
  参考文献：
  名称：

  'Click'-BINOLs：用于不对称催化的新型可调节配体

  摘要：

  摘要 新型易调节的1,2,3-三唑-BINOL配体'click'-BINOLs已使用功能强大的Huisgen [3 + 2]环加成'click'方法由易得的炔烃和几种叠氮基-BINOL衍生物合成。在醛的二乙基锌中，首次探索了这些配体在不对称路易斯酸催化中的活性。的c ^ 2 -对称配体1D显示了一个有趣的催化性能，这表明三唑单元的非无辜参与。因此，通过正确选择三唑环上的取代模式以及对反应条件进行微调，可以获得良好的对映选择性（ee高达86％）。 新型易调节的1,2,3-三唑-BINOL配体'click'-BINOLs已使用功能强大的Huisgen [3 + 2]环加成'click'方法由易得的炔烃和几种叠氮基-BINOL衍生物合成。在醛的二乙基锌中，首次探索了这些配体在不对称路易斯酸催化中的活性。的c ^ 2 -对称配体1D显示了一个有趣的催化性能，这表明三唑单元的非无辜参与。因此，通过正

  DOI：

  10.1055/s-0031-1291009

文献信息

• 'Click'-BINOLs: A New Class of Tunable Ligands for Asymmetric Catalysis
  作者：Olga Mancheño、Stephan Beckendorf

  DOI：10.1055/s-0031-1291009

  日期：2012.7

  Abstract A new class of easily tunable 1,2,3-triazole-BINOL ligands, 'click'-BINOLs, have been synthesized from readily available alkynes and several azido-BINOL derivatives using the powerful Huisgen [3+2] cycloaddition 'click' approach. The activity of these ligands in asymmetric Lewis acid catalysis has been explored for the first time in the diethylzinc addition to aldehydes. The C 2-symmetric

  摘要 新型易调节的1,2,3-三唑-BINOL配体'click'-BINOLs已使用功能强大的Huisgen [3 + 2]环加成'click'方法由易得的炔烃和几种叠氮基-BINOL衍生物合成。在醛的二乙基锌中，首次探索了这些配体在不对称路易斯酸催化中的活性。的c ^ 2 -对称配体1D显示了一个有趣的催化性能，这表明三唑单元的非无辜参与。因此，通过正确选择三唑环上的取代模式以及对反应条件进行微调，可以获得良好的对映选择性（ee高达86％）。 新型易调节的1,2,3-三唑-BINOL配体'click'-BINOLs已使用功能强大的Huisgen [3 + 2]环加成'click'方法由易得的炔烃和几种叠氮基-BINOL衍生物合成。在醛的二乙基锌中，首次探索了这些配体在不对称路易斯酸催化中的活性。的c ^ 2 -对称配体1D显示了一个有趣的催化性能，这表明三唑单元的非无辜参与。因此，通过正
• Fine‐Tuning Substrate–Catalyst Halogen–Halogen Interactions for Boosting Enantioselectivity in Halogen‐Bonding Catalysis
  作者：Alica C. Keuper、Kevin Fengler、Florian Ostler、Tobias Danelzik、Dariusz G. Piekarski、Olga García Mancheño

  DOI：10.1002/anie.202304781

  日期：2023.8.28

  A new approach towards highly enantioselective halogen‐bonding catalysis has been developed. To circumvent the intrinsic issues of the nature of the halogen‐bond (XB) and the resultant unresolved limitations in asymmetric catalysis, fine‐tuned halogen–halogen interactions between the substrate and XB‐donor were designed to preorganize the substrate in the catalyst's cavity and boost enantiocontrol. The present strategy exploits both the electron cloud (Lewis base site) and the sigma (σ)‐hole site of the halogen substituent of the substrates to form a tight catalyst–substrate–counteranion chiral complex, thus enabling a controlled induction of high levels of chirality transfer. Remarkable enantioselectivities of up to 95 : 5 e.r. (90 % ee) have been achieved in a model dearomatization reaction of halogen‐substituted (iso)quinolines with tetrakis‐iodotriazole multidentate anion‐binding catalysts.

  摘要 开发了一种实现高对映选择性卤素键催化的新方法。为了规避卤素键（XB）性质的固有问题以及由此导致的不对称催化中尚未解决的限制，设计了底物和 XB-载体之间的微调卤素-卤素相互作用，以便在催化剂空腔中预先组织底物并增强对映体控制。本策略同时利用了底物卤素取代基的电子云（路易斯碱基位点）和σ（σ）孔位点，形成了一个紧密的催化剂-底物-反阴离子手性复合物，从而实现了高水平手性转移的受控诱导。显著的对映体选择性高达 95 ：在卤素取代（异）喹啉与四烷基碘三唑多叉阴离子结合催化剂的脱芳烃反应模型中，实现了高达 95 : 5 e.r. （90 % ee）的显著对映选择性。
• Click Approaches to Functional Water-Sensitive Organotriethoxysilanes
  作者：Kristýna Bürglová、Nirmalya Moitra、Jana Hodačová、Xavier Cattoën、Michel Wong Chi Man

  DOI：10.1021/jo201484n

  日期：2011.9.16

  The derivatization of functional organic fragments with triethoxysilyl groups to afford hydrolyzable organosilanes with targeted properties using the copper-catalyzed alkyne azide cydoaddition reaction under strictly anhydrous conditions is described according to two approaches, starting from five silylated substrates. This high yield, fast, and selective method is applicable to a wide range of substrates and is expected to lead to important achievements in the field of functional hybrid silica.
• A novel BINOL-based cyclophane via click chemistry: synthesis and its applications for sensing silver ions
  作者：Ji-Ting Hou、Qin-Fang Zhang、Bang-Yu Xu、Qiao-Sen Lu、Qiang Liu、Ji Zhang、Xiao-Qi Yu

  DOI：10.1016/j.tetlet.2011.07.050

  日期：2011.9

  A novel BINOL-based cyclophane 1 incorporating two triazole moieties was synthesized via click chemistry and characterized. Among the metal ions screened, only Ag+ was found to have the ability to quench the fluorescence of 1 in methanol solution. The 1:1 binding mode of 1-Ag+ was confirmed. The competitive experiment showed that compound 1 can be used as a specific fluorescent sensor for Ag+ over a wide range of competing cations. (C) 2011 Elsevier Ltd. All rights reserved.