1-methoxy-3-(phenoxymethyl)benzene | 19962-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-methoxy-3-(phenoxymethyl)benzene
• 英文别名: 3-methoxybenzyl phenyl ether；m-Phenoxymethyl-anisol
• CAS: 19962-23-3
• 化学式: C₁₄H₁₄O₂
• mdl: MFCD21365907
• 分子量: 214.264
• InChiKey: PEQHTFRPJFPOFM-UHFFFAOYSA-N

物化性质

• 沸点：
  134-136 °C(Press: 0.2 Torr)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1-methoxy-3-(phenoxymethyl)benzene 以 乙腈 为溶剂， 反应 0.17h， 生成 o-Methoxybenzaldehyde 2,4-dinitrophenylhydrazone
  参考文献：
  名称：

  Substituent dependence of the .pi.-acceptor-induced bond cleavage reactions of benzyl phenyl ethers

  摘要：

  DOI：

  10.1021/jo00292a033
• 作为产物：
  描述：

  2-溴-5-甲氧基溴苄 在 palladium dihydroxide potassium acetate 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 丙酮 为溶剂， 生成 1-methoxy-3-(phenoxymethyl)benzene
  参考文献：
  名称：

  Direct Arylation Reactions Catalyzed by Pd(OH)₂/C:  Evidence for a Soluble Palladium Catalyst

  摘要：

  Palladium hydroxide on carbon (Pearlman's catalyst) effectively catalyzes direct arylation reactions of aryl iodides and bromides, providing excellent arylation-to-hydrodehalogenation ratios (> 30:1) with broad scope for both intra- and intermolecular arylation processes. Studies aimed at determining the nature of the active catalyst indicate that an active homogeneous palladium species is produced under the reaction conditions.

  DOI：

  10.1021/jo051039v

文献信息

• Metal-Free Synthesis of Aryl Ethers in Water
  作者：Erik Lindstedt、Raju Ghosh、Berit Olofsson

  DOI：10.1021/ol402960f

  日期：2013.12.6

  arylation of allylic and benzylic alcohols with diaryliodonium salts is reported. The reaction yields alkyl aryl ethers under mild and metal-free conditions. Phenols are arylated to diaryl ethers in good to excellent yields. The reaction employs diaryliodonium salts and sodium hydroxide in water at low temperature, and excess amounts of the coupling partners are avoided.

  据报道，烯丙基和苄基醇与二芳基碘鎓盐具有第一芳基化作用。该反应在温和且无金属的条件下产生烷基芳基醚。苯酚以良好或优异的产率芳基化为二芳基醚。该反应在低温下在水中使用二芳基碘鎓盐和氢氧化钠，避免了过量的偶合伴侣。
• Tetrabutyl ammonium bromide-mediated benzylation of phenols in water under mild condition
  作者：Hailei Wang、Yuping Ma、Heng Tian、Ajuan Yu、Junbiao Chang、Yangjie Wu

  DOI：10.1016/j.tet.2014.01.004

  日期：2014.4

  Benzylation of phenol was successfully achieved in water under room temperature mediated by tetrabutylammonium bromide (TBAB) for only 2 h affording the corresponding benzyl phenyl ether with good to excellent yields. This protocol is very efficient, simple, avoiding catalysts, easy to work-up after reaction, and especially ‘green’.

  在室温下，由四丁基溴化铵（TBAB）介导的苯酚在水中的苯甲酸酯化成功完成仅2小时，从而以良好或优异的收率获得了相应的苄基苯基醚。该方案非常有效，简单，避免了催化剂，反应后易于后处理，尤其是“绿色”。
• Samarium(II)-Mediated Spirocyclization by Intramolecular Aryl Radical Addition onto an Aromatic Ring
  作者：Hiroki Iwasaki、Toru Eguchi、Nozomi Tsutsui、Hiroaki Ohno、Tetsuaki Tanaka

  DOI：10.1021/jo800656a

  日期：2008.9.19

  Samarium(II)-mediated spirocyclization by intramolecular addition of aryl radicals onto an aromatic ring was achieved by the reaction of N-(2-iodophenyl)-N-alkylbenzamides with SmI2 in the presence of HMPA, yielding spirocyclic indolin-2-one derivatives. The ether congeners afford spirocyclic benzofuran derivatives in moderate yields by aryl radical addition onto a benzene ring without having an electron-withdrawing

  N-（2-碘苯基）-N-烷基苯甲酰胺与SmI2在HMPA存在下反应，通过在芳环上分子内加成芳基，将mar（II）介导的螺环化反应，生成螺环吲哚-2-酮衍生物。醚同类物通过在不具有吸电子基团的情况下将芳基自由基加成到苯环上而以中等收率得到螺环苯并呋喃衍生物。还描述了与其他芳基如萘和吲哚环的反应。
• Pd-Catalyzed Homologation of Arylboronic Acids as a Platform for the Diversity-Oriented Synthesis of Benzylic C–X Bonds
  作者：Allan J. B. Watson、Kane A. C. Bastick

  DOI：10.1055/a-2117-9878

  日期：2023.11

  platform for the formation of benzylic C–X bonds. Benzylboronic acid pinacol (Bpin) esters are useful synthetic intermediates but are commercially uncommon, leading to preparations that typically rely upon stoichiometric metalation. Pd-catalyzed formal homologation of arylboronic acids provides access to these compounds that, in turn, allow the formation of C–C, C–O, and C–N bonds from Pd- and Cu-mediated

  我们报告了一个用于形成苄基 C-X 键的合成平台。苄基硼酸频哪醇 (Bpin) 酯是有用的合成中间体，但在商业上并不常见，导致其制备通常依赖于化学计量金属化。钯催化的芳基硼酸的形式同系化提供了获得这些化合物的途径，这些化合物反过来又允许通过钯和铜介导的交叉偶联或氧化过程形成 C-C、C-O 和 C-N 键。这提供了多种苄醇、二芳基甲烷、苄胺和苄基醚。公开了其局限性，并且通过氯苯甲嗪类似物的产生进一步证明了其实用性。
• Heat-curing epoxy resin composition containing non-aromatic ureas as accelerator
  申请人：SIKA TECHNOLOGY AG

  公开号：US11198754B2

  公开（公告）日：2021-12-14

  Heat-curing epoxy resin compositions are characterized by high impact strength, good storage stability, and a low curing temperature. The epoxy resin compositions are suitable for use as a construction shell adhesive and for producing structural foams. They can already be cured in so-called bottom-baking conditions. Furthermore, it has been found that the use of an accelerator of the formula (Ia) or (Ib) results in an increase of the impact strength of heat-curing epoxy resin compositions.

  热固化环氧树脂组合物具有冲击强度高、储存稳定性好和固化温度低的特点。环氧树脂组合物适合用作建筑外壳粘合剂和生产结构泡沫。它们已经可以在所谓的底部烘烤条件下固化。此外，还发现使用式（Ia）或（Ib）的促进剂可提高热固化环氧树脂组合物的抗冲击强度。