2-(2-甲氧基苯氧基)苯甲醛 | 62256-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-甲氧基苯氧基)苯甲醛
• 英文名称: 2-(2-methoxyphenoxy)benzaldehyde
• CAS: 62256-40-0
• 化学式: C₁₄H₁₂O₃
• mdl: MFCD11156494
• 分子量: 228.247
• InChiKey: LXJAXYDYHJZNPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-甲氧基苯氧基)苯甲醛 在 氢氧化钾 、 氢溴酸 、 溶剂黄146 、 lithium chloride 作用下， 以 水 为溶剂， 反应 56.0h， 生成 2-(2-hydroxyphenoxy)-α-bromobenzeneacetic acid
  参考文献：
  名称：

  Synthesis of new fenmetazole analogues with potential mixed α2-adrenergic antagonistic activity and noradrenaline-uptake inhibiting properties

  摘要：

  In the search for new antidepressants with a rapid onset of action, fenmetazole analogues, bearing a second phenyl ring in a position previously shown not to be detrimental to affinity and selectivity for the alpha-2-adrenoreceptors, were synthesized in an attempt to combine NA-uptake inhibition and blockade of the alpha-2-adrenoreceptors in the same molecule. Some of the new molecules showed enhanced affinity and selectivity for the alpha-2-adrenoreceptors compared to fenmetazole. Surprisingly, introduction of a phenyl ring in the structure of fenmetazole changed the agonistic action of the parent compound toward the alpha-1-adrenoreceptors into an antagonistic effect. However, none of the new derivatives showed in vitro NA-uptake inhibitory potency substantially different from the low activity of fenmetazole in this test.

  DOI：

  10.1016/0223-5234(91)90031-h
• 作为产物：
  描述：

  2-氟苯甲醛 、 木榴油 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 6.0h， 以70%的产率得到2-(2-甲氧基苯氧基)苯甲醛
  参考文献：
  名称：

  无金属的氧化偶联：通过四丁基溴化铵作为促进剂，在水性介质中直接环合2-芳氧基苯甲醛制得的蒽酮

  摘要：

  AbstractA metal‐free intramolecular annulation of 2‐aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde CH bond and aromatic CH bonds using tetrabutylammonium bromide (TBAB) as a promoter in aqueous medium. This strategy works smoothly in the presence of both electron‐donating and electron‐withdrawing groups, and displays good tolerance towards catalytically reactive substituents, thus promising further functionalizations of xanthone products.magnified image

  DOI：

  10.1002/adsc.201300488

文献信息

• Photoinduced transition-metal- and external-photosensitizer-free intramolecular aryl rearrangement <i>via</i> C(Ar)–O bond cleavage
  作者：Qian Dou、Chao-Jun Li、Huiying Zeng

  DOI：10.1039/d0sc01585g

  日期：——

  halogen, and heteroaromatic rings. Control experiments suggested that the reaction proceeded via a photoinduced intramolecular heteroaryl/aryl rearrangement process involving photoexcitation of the aldehyde carbonyl group, radical addition, C–C bond formation and C(Ar)–O bond cleavage.

  使用不需要昂贵的光催化剂或过渡金属的光化学反应是完成各种结构转变的环境友好策略。在此，我们报告了 2-杂芳基/芳氧基苯甲醛的光诱导无过渡金属和无外部光催化剂的分子内杂芳基/芳基重排反应的方案。该方案与多种官能团兼容，包括甲基、甲氧基、氰基、酯、三氟甲基、卤素和杂芳环。对照实验表明，该反应通过光诱导的分子内杂芳基/芳基重排过程进行，涉及醛羰基的光激发、自由基加成、C-C键形成和C(Ar)-O键断裂。
• Novel Diazaspiroalkanes and Their Use for Treatment of CCR8 Mediated Diseases
  申请人：Connolly Stephen

  公开号：US20090118318A1

  公开（公告）日：2009-05-07

  The invention provides compounds of general formula wherein R and R 1 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了通式化合物，其中R和R1如规范中所定义，其制备方法，含有它们的制药组合物以及它们在治疗中的用途。
• NOVEL DIAZASIPIROAKANES AND THEIR USE FOR TREATMENT OF CCR8 MEDIATED DISEASES
  申请人：Connolly Stephen

  公开号：US20110053969A1

  公开（公告）日：2011-03-03

  The invention provides compounds of general formula. (II) wherein R and are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了一般式（II）的化合物，其中R和均如规范中定义，其制备过程，包含它们的制药组合物以及它们在治疗中的应用。
• Increasing Selectivity of CC Chemokine Receptor 8 Antagonists by Engineering Nondesolvation Related Interactions with the Intended and Off-Target Binding Sites
  作者：Igor Shamovsky、Chris de Graaf、Lisa Alderin、Malena Bengtsson、Håkan Bladh、Lena Börjesson、Stephen Connolly、Hazel J. Dyke、Marco van den Heuvel、Henrik Johansson、Bo-Göran Josefsson、Anna Kristoffersson、Tero Linnanen、Annea Lisius、Roope Männikkö、Bo Nordén、Steve Price、Lena Ripa、Didier Rognan、Alexander Rosendahl、Marco Skrinjar、Klaus Urbahns

  DOI：10.1021/jm900713y

  日期：2009.12.10

  The metabolic stability and selectivity of a series of CCR8 antagonists against binding to the hERG ion channel and cytochrome Cyp2D6 are studied by principal component analysis. It is demonstrated that an efficient way of increasing metabolic stability and selectivity of this series is to decrease compound lipophilicity by engineering nondesolvation related attractive interactions with CCR8, as rationalized by three-dimensional receptor models. Although Such polar interactions led to increased compound selectivity, such a strategy could also jeopardize the DMPK profile of compounds. However, once increased potency is found, the lipophilicity can be readjusted by engineering hydrophobic substituents that fit to CCR8 but do not fit to hERG. Several such lipophilic fragments are identified by two-dimensional fragment-based QSAR analysis. Electrophysiological measurements and site-directed mutagenesis studies indicated that the repulsive interactions of these fragments with hERG are caused by steric hindrances with residue F656.
• Synthesis and Reactions of Some Dibenzoxepins
  作者：Richard H. F. Manske、Archie E. Ledingham

  DOI：10.1021/ja01166a128

  日期：1950.10