6-nitro-2-methoxy-2'-pivaloyloxy-1,1'-binaphthyl | 537014-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-nitro-2-methoxy-2'-pivaloyloxy-1,1'-binaphthyl
• 英文别名: [1-(2-Methoxy-6-nitronaphthalen-1-yl)naphthalen-2-yl] 2,2-dimethylpropanoate；[1-(2-methoxy-6-nitronaphthalen-1-yl)naphthalen-2-yl] 2,2-dimethylpropanoate
• CAS: 537014-47-4
• 化学式: C₂₆H₂₃NO₅
• 分子量: 429.472
• InChiKey: HYAGEZRBEOJPTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-nitro-2-methoxy-2'-pivaloyloxy-1,1'-binaphthyl 在 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以55%的产率得到2'-methoxy-6'-nitro-[1,1'-binaphthalen]-2-ol
  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
• 作为产物：
  描述：

  (S)-2-hydroxy-2'-pivaloyloxy-1,1'-binaphthyl 在 硫酸 、 硝酸 、 potassium carbonate 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 26.0h， 生成 6-nitro-2-methoxy-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

• 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.
• The artificial binaphthyl amino acid 6-amino-6′-carboxyethyl-2-methoxy-2′-hydroxy-1,1′-binaphthyl (Bna): synthesis and assembly of Bna peptides
  作者：Melanie Thoß、Rüdiger W. Seidel、Martin Feigel

  DOI：10.1016/j.tet.2010.08.066

  日期：2010.10

  The new binaphthyl-based amino acid 6-amino-6'-carboxyethyl-2-methoxy-2'-hydroxy-1,1'-binaphthyl (Bna) is presented, which combines the axially chiral binaphthyl core, a phenolic OH-group as well as terminating amino and carboxyl groups in one structure. The large aromatic rings of the compound provide molecular spacing and pi-surface attraction in assembled Bna oligoamides. The synthesis of Bna derivatives is reported, both with the (R)- and with the (S)-binaphthyl skeleton. Several dipeptides of (R)or (S)-Bna units combined with natural amino acids, were prepared as 'building blocks' for the synthesis of extended Boa peptides. The tetrapeptide Boc-(S)-Val-(S)-Bna(OH)-(S)-Val-(S)-Bna(OPiv)-O-n-But (12) and the pentapeptide Boc-(S)-Val-(S)-Bna(OH)-(S)-Val-(S)-Bna(OH)-Gly-OH (13) were prepared via conventional solution phase synthesis and solid phase synthetic techniques, respectively. Compound 12 shows an interesting dynamic H-1 NMR spectrum suggesting compact and aggregated forms in dichloromethane. Compound 13 accelerates the enolisation of acetone. The use of more complex Bna peptides as organo catalysts is proposed. (C) 2010 Elsevier Ltd. All rights reserved.
• Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion
  作者：Benjamin A. Jones、Tudor Balan、John D. Jolliffe、Craig D. Campbell、Martin D. Smith

  DOI：10.1002/anie.201814381

  日期：2019.3.26

  BINOLs are valuable and widely used building blocks, chiral ligands, and catalysts that are effective across a remarkable range of different chemical transformations. Here we demonstrate that an ammonium salt catalyzed kinetic resolution of racemic BINOLs with benzyl tosylate proceeds with s up to 46. This is a scalable and practical process that can be applied across >30 different C2‐ and non‐C2‐symmetric

  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