2-benzyloxy-4-methoxy iodobenzene | 193333-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-benzyloxy-4-methoxy iodobenzene
• 英文别名: 2-(benzyloxy)-1-iodo-4-methoxybenzene；1-iodo-4-methoxy-2-phenylmethoxybenzene
• CAS: 193333-17-4
• 化学式: C₁₄H₁₃IO₂
• 分子量: 340.161
• InChiKey: CTXYAZQJJQLGGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzyloxy-4-methoxy iodobenzene 在 copper(l) iodide 、 三溴化硼 、 三苯基膦 、 palladium dichloride 作用下， 以 二氯甲烷 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 4-bromo-7-methoxy-2,2-dimethyl-2H-chromene
  参考文献：
  名称：

  Cyclization of o-(3-Hydroxy-3-methylbutynyl)phenols with Boron Tribromide to 4-Bromo-2,2-dimethylchromenes and Their Electroreduction to 2,2-Dimethylchromenes

  摘要：

  Cyclization of o-(3-hydroxy-3-methylbutynyl)phenols (2) with boron tribromide gave easily 4-bromo-2,2-dimethylchromenes (3). Electrolytic reduction of 3 at a Hg-pool electrode afforded the corresponding 2,2-dimethylchromenes (6) in high yields.

  DOI：

  10.3987/com-97-7804
• 作为产物：
  描述：

  甲醇 、 2-苄氧基-4-氟-1-碘苯 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 以90%的产率得到2-benzyloxy-4-methoxy iodobenzene
  参考文献：
  名称：

  Regioselectivity of fluorine substitution by alkoxides on unsymmetrical difluoroarenes

  摘要：

  An efficient approach to unsymmetrical halogenated resorcinol diethers has been developed. This synthesis consists of two subsequent nucleophilic aromatic substitutions (S(N)Ar) of unsymmetrical difluoroarenes by alkoxides. The novelty of this approach is its control of regioselectivity during the first SNAr, which occurs at room temperature. Interestingly, the reactivity of competing fluorines was correlated to their chemical shift in (19)F NMR. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.091

文献信息

• Photo-catalyzed sequential dearomatization/carboxylation of benzyl o-halogenated aryl ether with CO2 leading to spirocyclic carboxylic acids
  作者：Yaping Yi、Chanjuan Xi

  DOI：10.1016/s1872-2067(21)63956-6

  日期：2022.7

  Photo-catalyzed tandem dearomatization/carboxylation of benzyl o-halogenated aryl ether with CO2 was achieved, which affords spirocyclic carboxylic acids under mild conditions. The reaction has good functional group tolerance with high yields. Mechanism studies indicate that the transformation was realized via intramolecular radical addition and nucleophilic addition.

  实现了用CO 2对苄基邻卤代芳基醚进行光催化的串联脱芳构化/羧化，在温和条件下得到螺环羧酸。该反应具有良好的官能团耐受性和高收率。机理研究表明，转化是通过分子内自由基加成和亲核加成实现的。
• Aryl–aryl cross-coupling reactions without reagents or catalysts: photocyclization of <i>ortho</i>-iodoaryl ethers and related compounds <i>via</i> triplet aryl cation intermediates
  作者：Wei Sun、Luke Wilding-Steele、Richard C. D. Brown、David C. Harrowven

  DOI：10.1039/d3cc03271j

  日期：——

  Cyclisations of benzyl ortho-iodoaryl ethers to benzo[c]chromenes can be effected without reagents or catalysts by irradiation with UVC under flow. Reactions proceed via triplet aryl cation generation, 5-exo and 3-exo-cyclisations, and rearomatisation. They have wide scope, are easy to effect and extend to a myriad of related ring systems.

  苄基邻碘芳基醚环化成苯并[ c ]色烯可以在没有试剂或催化剂的情况下通过在流动下用UVC照射来实现。反应通过三线态芳基阳离子生成、5-外型和3-外型环化以及重新芳构化进行。它们的范围很广，很容易实现并扩展到无数相关的环系统。
• CN115594582
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• CN115286605
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