6-bromo-7-(methoxymethoxy)naphthalen-2-ol | 171192-57-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-bromo-7-(methoxymethoxy)naphthalen-2-ol
• CAS: 171192-57-7
• 化学式: C₁₂H₁₁BrO₃
• 分子量: 283.122
• InChiKey: KNESERSNKNXRBL-UHFFFAOYSA-N

物化性质

• 沸点：
  419.2±35.0 °C(Predicted)
• 密度：
  1.530±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-7-(methoxymethoxy)naphthalen-2-ol 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 盐酸 、 copper(l) iodide 、 正丁基锂 、 四甲基乙二胺 、 碘 、 potassium carbonate 、 叔丁胺 、 二乙胺 、 copper dichloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成 7,7'-Bis-benzyloxy-3,3'-diethynyl-2,2'-bis-methoxymethoxy-[1,1']binaphthalenyl
  参考文献：
  名称：

  Molecular Recognition of Pyranosides by a Family of Trimeric, 1,1′-Binaphthalene-Derived Cyclophane Receptors

  摘要：

  The synthesis and carbohydrale-recognition properties of a new family of optically active cyclophane receptors, 1-3, in which three 1,1'-binaphthalene-2,2'-diol spacers are interconnected by three bula-1,3-diynediyl linkers, are described. The macrocycles all contain highly preorganized cavities lined with six convergent OH groups for H-bonding and complementary in size and shape to monosaccharides. Compounds 1-3 differ by the functionality attached to the major groove of the 1,1'-binaphthalene-2.2'-diol spacers. The major grooves of the spacers in 2 are unsubstituted, whereas those in 1 bear benzyloxy (BnO) groups in the 7,7'-positions and those in 3 2-phenylethyl groups in the 6,6'-positions. The preparation of the more planar, D-3-symmetrical receptors (R,R,R)-1(Schemes I and 2), (S,S;S)-1 (Scheme 4), (S,S,S)-2 (Scheme 5), and (S,S,S)-3 (Scheme 8) involved as key step the Glaser-Hay cyclotrimerization of the corresponding OH-protected 3,3'-dielhynyl-1,1'-binaphthalene-2,2'-diol precursors, which yielded tetrameric and pentameric macrocycles in addition to the desired trimeric compounds. The synthesis of the less planar, C-2-symmetrical receptors (R,R,S)-2 (Scheme 6) and (S,S,R)-3 (Scheme 9) proceeded via two Glaser-Hay coupling steps. First, two monomeric precursors of identical configuration were oxidatively coupled to give a dimeric intermediate which was then subjected to macrocyclization with a third monomeric 1,1'-binaphthalene precursor of opposite configuration. The 3,3'-dialkynylation of the OH-protected 1,1'-binaphthalene-2,2'-diol precursors for the macrocyclizations was either performed by Stifle (Scheme I) or by Sonogashira (Schemes 4, 5, and 8) cross-coupling reactions. The flat D-3-symmetrical receptors (R,R,R)-1 and (S,S,S)-1 formed 1:1 cavity inclusion complexes with octyl 1-O-pyranosides in CDCl3 (300 K) with moderate stability (Delta G degrees ca. -3 kcal mol(-1)) as well as moderate diastereo(Delta(Delta G degrees) up to 0.7 kcal mol(-1)) and enantioselectivity (Delta(Delta G degrees) = 0.4 kcal mol(-1)) ( Table I). Stoichiometric 1 : 1 complexation by (S,S,S)-2 and (S,S,S)3 could not be investigated by H-1-NMR binding titrations, due to very strong signal broadening. This broadening of the H-1-NMR resonances is presumably indicative of higher-order associations, in which the planar macrocycles sandwich the carbohydrate guests. The less planar Ct-symmetrical receptor (S,S,R)-3 formed stable 1: 1 complexes with binding free enthalpies of up to Delta G degrees = - 5.0 kcal mol(-1) (Table 2). With diastereoselectivities up to Delta(Delta G degrees)=1.3 kcal mol(-1) and enantioselectivities of Delta(Delta G degrees)= 0.9 kcal mol(-1), (S,S,R)-3 is among the most selective artificial carbohydrate receptors known.

  DOI：

  10.1002/(sici)1522-2675(19981111)81:11<1931::aid-hlca1931>3.0.co;2-5
• 作为产物：
  描述：

  3-bromonaphthalene-2,7-diol 、 氯甲基甲基醚 在 三乙胺 作用下， 以 乙腈 为溶剂， 以57%的产率得到6-bromo-7-(methoxymethoxy)naphthalen-2-ol
  参考文献：
  名称：

  尼古拉斯反应在庚建设[德]萘和庚[德]萘酮。微甾醇的全合成

  摘要：

  2,7-二氧化萘的尼古拉斯反应化学在环庚的合成[应用德]萘并在合成（±）-microstegiol（1）的设计。据报道，尼古拉斯单取代（主要为C-1）的取代特征和2,7-二加氧萘的解离反应（主要为1,6-）。1,8- dicondensation产物和应用选择的C-1 monocondensation产品环庚的构造[ DE ]通过闭环复分解的和分子内Friedel-Crafts反应方式萘，分别进行说明。在C-7氧功能为相应的萘酚的脱保护可以互变异构化至环庚[日在大多数情况下，在七元环闭合时]]萘-1-酮以及用甲基取代萘中的C-2氧官能团最终可以合成（±）-微甜菊醇。

  DOI：

  10.1021/jo102127q

文献信息

• [EN] COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS<br/>[FR] COMPOSÉS EN TANT QU'INHIBITEURS DE LA S-NITROSOGLUTATHION RÉDUCTASE
  申请人：N30 PHARMACEUTICALS LLC

  公开号：WO2012170371A1

  公开（公告）日：2012-12-13

  The present invention is directed to compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.

  本发明涉及用作S-亚硝基谷胱甘肽还原酶（GSNOR）抑制剂的化合物，包括该化合物的制药组合物以及使用该化合物的方法。
• Novel Substituted Bicyclic Aromatic Compounds as S-Nitrosoglutathione Reductase Inhibitors
  申请人：Sun Xicheng

  公开号：US20130261122A1

  公开（公告）日：2013-10-03

  The present invention is directed to novel substituted bicyclic aromatic compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.

  本发明涉及一种新型的取代双环芳香化合物，可用作S-亚硝基谷胱甘肽还原酶（GSNOR）抑制剂，包括此类化合物的制药组合物以及制备和使用它们的方法。
• Compounds as S-Nitrosoglutathione Reductase Inhibitors
  申请人：N30 PHARMACEUTICALS, INC.

  公开号：US20140094465A1

  公开（公告）日：2014-04-03

  The present invention is directed to compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.

  本发明涉及用作S-亚硝基谷胱甘肽还原酶（GSNOR）抑制剂的化合物，包括这种化合物的制药组合物，以及使用它们的方法。
• Anderson, Sally; Neidlein, Ulf; Gramlich, Volker, Angewandte Chemie, 1995, vol. 107, # 15, p. 1722 - 1725
  作者：Anderson, Sally、Neidlein, Ulf、Gramlich, Volker、Diederich, Francois

  DOI：——

  日期：——
• NOVEL SUBSTITUTED BICYCLIC AROMATIC COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
  申请人：N30 Pharmaceuticals, Inc.

  公开号：EP2651871A1

  公开（公告）日：2013-10-23