2-hydroxy-6-nitro-2'-pivaloyloxy-1,1'-binaphthyl | 537014-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-6-nitro-2'-pivaloyloxy-1,1'-binaphthyl
• 英文别名: 2'-hydroxy-6'-nitro-[1,1'-binaphthalen]-2-yl pivalate；6-nitro-2-hydroxy-2'-pivaloyloxy-1,1'-binaphthyl；[1-(2-hydroxy-6-nitronaphthalen-1-yl)naphthalen-2-yl] 2,2-dimethylpropanoate
• CAS: 537014-46-3
• 化学式: C₂₅H₂₁NO₅
• 分子量: 415.445
• InChiKey: XXQCOZNUDGSSDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-6-nitro-2'-pivaloyloxy-1,1'-binaphthyl 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以99%的产率得到(R)-6-nitro-2,2'-dihydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  通过前所未有的光驱动轴向手性分子开关实现自组织螺旋上层结构的可逆可见光调谐

  摘要：

  发现两个具有轴向手性和扩展共轭的对映体光驱动偶氮分子开关仅在可见光照射下在有机溶剂和液晶介质中表现出前所未有的可逆光异构化。当掺杂不同浓度的非手性液晶时，手性开关能够立即诱导光学可调螺旋超结构，或保留非手性液晶相，其螺旋超结构在可见光照射下被可逆地诱导和调谐。此外，还展示了仅通过使用可见光实现的可逆动态红色、绿色和蓝色反射。

  DOI：

  10.1021/ja211837f
• 作为产物：
  描述：

  三甲基乙酰氯 在 硫酸 、 硝酸 、 三乙胺 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 7.0h， 生成 2-hydroxy-6-nitro-2'-pivaloyloxy-1,1'-binaphthyl
  参考文献：
  名称：

  实用和可扩展的动力学拆分手性抗衡的BINOLs。

  摘要：

  BINOLs是有价值的且被广泛使用的结构单元，手性配体和催化剂，它们在各种化学转化的显着范围内均有效。在这里，我们证明了铵盐催化外消旋BINOLs与甲苯磺酸苄酯的动力学拆分可至s高达46。这是一种可扩展且实用的方法，可应用于> 30种不同的C 2-和非C 2-对称BINOL。该方法的实施使对映体可以广泛地与99：1 er的BINOL衍生物进行对映选择性合成

  DOI：

  10.1002/anie.201814381

文献信息

• Facile synthesis of 6-iodo-2,2′-dipivaloyloxy-1,1′-binaphthyl, a key intermediate of high reactivity for selective palladium-catalyzed monofunctionalization of the 1,1′-binaphthalene core
  作者：Csaba Fehér、Béla Urbán、László Ürge、Ferenc Darvas、József Bakos、Rita Skoda-Földes

  DOI：10.1016/j.tetlet.2010.05.022

  日期：2010.7

  A high-yielding procedure for selective monoiodination of 2,2′-dihydroxy-1,1′-binaphthyl (BINOL) is reported. 6-Iodo-2,2′-dipivaloyloxy-1,1′-binaphthyl, obtained in three steps starting from BINOL in 88% overall yield, proved to be a highly efficient substrate in various palladium-catalyzed coupling (Stille, Heck, Sonogashira, and Suzuki coupling) and carbonylation reactions compared to the analogous

  报道了2,2'-二羟基-1,1'-联萘（BINOL）选择性单碘化的高产程序。从BINOL分三步获得的6-碘2,2'-二戊酰氧基-1,1'-联萘基以88％的总收率被证明是各种钯催化偶联的高效底物（Stille，Heck，Sonogashira ，和Suzuki偶联）和羰基化反应（与类似的6-溴衍生物比较）。
• A Bidirectional Tunnel-like Structure with a Rigid, Thick, and Chiral Aromatic Macrocycle Prepared by Self-complementary 6,6′-Substituted Binaphthyl Monomer
  作者：Kazuhiro Kumeda、Munetosi Ono、Atsushi Kawai、Hideaki Oike、Keiichi Noguchi、Noriyuki Yonezawa

  DOI：10.1246/cl.2008.660

  日期：2008.6.5

  A rigid, thick, and optically active aromatic macrocycle having 6,6′-binaphthylylene moieties was successfully obtained in a moderate yield by synthesis and SNAr of 6-(4-fluorobenzoyl)-6′-hydroxy-2,2′-dimethoxy-1,1′-binaphthyl. The X-ray crystal structural analysis of the obtained macrocycle reveals rigid concavo–concave shape of the molecule and the bidirectional tunnel-like structure assembly consisting of two types of channels along a axis and c axis originated by intra- and intermolecular cavities, respectively.

  通过合成 6-(4-氟苯甲酰基)-6′-羟基-2,2′-二甲氧基-1,1′-联萘并对其进行 SNAr 处理，成功地获得了一种具有 6,6′-联萘分子的刚性、厚实且光学活性高的芳香族大环，收率中等。对所得到的大环化合物进行的 X 射线晶体结构分析表明，该分子呈刚性凹凸形状，由分子内空穴和分子间空穴分别形成的沿 a 轴和 c 轴的两类通道组成的双向隧道状结构组装体。
• A simple synthetic approach to homochiral 6- and 6′-substituted 1,1′-binaphthyl derivatives
  作者：Heiko Hocke、Yasuhiro Uozumi

  DOI：10.1016/s0040-4020(02)01584-3

  日期：2003.1

  Various homochiral binaphthyl derivatives having functional groups at the 6-position are important key intermediates for the immobilization of binaphthyl compounds on various solid-supports and have been prepared from commercially available 1,1'-bi-2-naphthol via controlled monopivalation of the 2-hydroxyl group and electrophilic aromatic substitution at the 6-position. (S)-2,2'-Bis-((S)-4-alkyloxazol-2-yl)-6-(2-methoxycarbonyl)ethyl-1,1'-binaphthyls (6-functionalized (S,S)-boxax)) were prepared and immobilized on various polymer supports including PS-PEG, PS, PEGA and MeO-PEG resin. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Structural characterization of racemic 1,1′-bi-(2-naphthol) monopivalate and its 6-nitro derivative
  作者：Melanie Thoß、Rüdiger W. Seidel、Iris M. Oppel、Martin Feigel

  DOI：10.1016/j.molstruc.2010.07.026

  日期：2010.9

  Racemic forms of 1,1 '-bi-(2-naphthol) (BINOL) monopivalate (rac-1) and its 6-nitro substitute (rac-2) were structurally characterized by X-ray crystallography. Molecules of opposite chirality form dimers in the crystalline state of rac-1 through O-H...O hydrogen-bonds between the free hydroxy and the pivalate carbonyl group. In contrast, polymeric hydrogen-bonded homo chiral chains were encountered for rac-2. In both rac-1 and rac-2, the dihedral angle between the naphthyl systems shows a significant deviation compared to the approximate 90 degrees angle of BINOL. As expected, compound rac-1 exhibits an increased angle (108.80(4)degrees and 102.09(4)degrees) as one of the hydroxy groups in BINOL is replaced by the sterically demanding pivaloyl ester. In contrast, the angle is decreased to 72.0(2)degrees in the nitro derivative rac-2. (C) 2010 Elsevier B.V. All rights reserved.