7-(benzyloxy)-3-bromonaphthalen-2-ol | 171192-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-(benzyloxy)-3-bromonaphthalen-2-ol
• 英文别名: 3-Bromo-7-phenylmethoxynaphthalen-2-ol
• CAS: 171192-59-9
• 化学式: C₁₇H₁₃BrO₂
• 分子量: 329.193
• InChiKey: CHHPZFQMOALNCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(benzyloxy)-3-bromonaphthalen-2-ol 在 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基苯酚 、 potassium carbonate 、 叔丁胺 、 copper dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 (+)-(R)-7,7'-bis(benzyloxy)-3,3'-diethynyl-1,1'-binaphthalene-2,2'-diyl dibenzoate
  参考文献：
  名称：

  Anderson, Sally; Neidlein, Ulf; Gramlich, Volker, Angewandte Chemie, 1995, vol. 107, # 15, p. 1722 - 1725

  摘要：

  DOI：
• 作为产物：
  描述：

  3-bromonaphthalene-2,7-diol 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 7-(benzyloxy)-3-bromonaphthalen-2-ol
  参考文献：
  名称：

  Anderson, Sally; Neidlein, Ulf; Gramlich, Volker, Angewandte Chemie, 1995, vol. 107, # 15, p. 1722 - 1725

  摘要：

  DOI：

文献信息

• Nicholas Reactions in the Construction of Cyclohepta[<i>de</i>]naphthalenes and Cyclohepta[<i>de</i>]naphthalenones. The Total Synthesis of Microstegiol
  作者：Rafiq A. Taj、James R. Green

  DOI：10.1021/jo102127q

  日期：2010.12.3

  construction of cyclohepta[de]naphthalenes by way of ring closing metathesis and intramolecular Friedel−Crafts reactions, respectively, is described. Deprotection of the C-7 oxygen function to the corresponding naphthol allows tautomerization to cyclohepta[de]naphthalene-1-ones upon seven-membered-ring closure in most cases, and replacement of the C-2 oxygen function in the naphthalene by a methyl group ultimately

  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。
• 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：——
• Molecular Recognition of Pyranosides by a Family of Trimeric, 1,1′-Binaphthalene-Derived Cyclophane Receptors
  作者：Anja Bähr、Anne Sophie Droz、Martin Püntener、Ulf Neidlein、Sally Anderson、Paul Seiler、François Diederich

  DOI：10.1002/(sici)1522-2675(19981111)81:11<1931::aid-hlca1931>3.0.co;2-5

  日期：1998.11.11

  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.