1-(benzyloxy)-2,4-dimethoxy-3-methylbenzene | 185981-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(benzyloxy)-2,4-dimethoxy-3-methylbenzene
• 英文别名: 1,3-Dimethoxy-2-methyl-4-phenylmethoxybenzene
• CAS: 185981-74-2
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: JIJYYBJWZNLIQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)-2,4-dimethoxy-3-methylbenzene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以90%的产率得到1-(benzyloxy)-5-bromo-2,4-dimethoxy-3-methylbenzene
  参考文献：
  名称：

  区域选择性亲电芳香溴化：理论分析和实验验证。

  摘要：

  亲电芳香溴化是用于制备芳基溴化物的最常用合成方法，芳基溴化物是有机合成中非常有用的中间体。为了理解亲电芳族溴化的实验结果，这里使用从头计算来对位置选择性进行初步分析。计算结果与相应的实验数据吻合较好，所得位置选择性的可靠性得到相应的实验数据的验证。

  DOI：

  10.3390/molecules19033401
• 作为产物：
  描述：

  2,4-dimethoxy-3-methylbenzoic acid 在 sodium methylate 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 1-(benzyloxy)-2,4-dimethoxy-3-methylbenzene
  参考文献：
  名称：

  Biaryl formation using the suzuki protocol: Considerations of base, halide, and protecting group.

  摘要：

  The generation of aryl anions prior to quenching with a trialkyl borate has been shown to be sensitive to the composition of the aryl substrate. Aryl iodides containing remote benzyl ether substituents undergo trans-metallation with sec-BuLi to cleanly give the desired aryl anions whereas the corresponding bromides afford appreciable quantities of dianionic intermediates. The arylboronic acids derived from alkylation of these anions subsequently undergo a palladium mediated coupling with aryl halides to provide good yields of the desired biaryls. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02065-5

文献信息

• Regioselective Electrophilic Aromatic Bromination: Theoretical Analysis and Experimental Verification
  作者：Hui-Jing Li、Yan-Chao Wu、Jian-Hong Dai、Yan Song、Runjiao Cheng、Yuanyuan Qiao

  DOI：10.3390/molecules19033401

  日期：——

  Electrophilic aromatic bromination is the most common synthetic method used to prepare aryl bromides, which are very useful intermediates in organic synthesis. To understand the experimental results in electrophilic aromatic brominations, ab initio calculations are used here for a tentative analysis of the positional selectivity. The calculated results agree well with the corresponding experimental

  亲电芳香溴化是用于制备芳基溴化物的最常用合成方法，芳基溴化物是有机合成中非常有用的中间体。为了理解亲电芳族溴化的实验结果，这里使用从头计算来对位置选择性进行初步分析。计算结果与相应的实验数据吻合较好，所得位置选择性的可靠性得到相应的实验数据的验证。
• Asymmetric Total Syntheses of (−)-Renieramycin M and G and (−)-Jorumycin Using Aziridine as a Lynchpin
  作者：Yan-Chao Wu、Jieping Zhu

  DOI：10.1021/ol9024919

  日期：2009.12.3

  By exploring the triple reactivity of two aziridines and double nucleophilicity of two aromatics, convergent and versatile syntheses of the above four natural products were developed.
• Stepwise Mechanism for the Bromination of Arenes by a Hypervalent Iodine Reagent
  作者：Albert Granados、Alexandr Shafir、Ana Arrieta、Fernando P. Cossío、Adelina Vallribera

  DOI：10.1021/acs.joc.9b02784

  日期：2020.2.21

  A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes

  使用双（三氟乙酰氧基）碘苯苄酯和三甲基甲硅烷基溴化物的组合，开发了一种温和，无金属的芳烃溴化方法。提出了原位形成的二溴（苯基）-λ3-碘（PhIBr2）作为反应中间体。使用PIFA / TMSBr的这种方法已成功应用于大量基材（25个实例）。单取代的活化芳烃的处理产生对溴化产物（2u-z），产率高达83-96％。密度泛函理论计算表明了一种逐步机理，该机理涉及添加双溴，然后进行II型正离子反应，并伴随六元环的重新芳构化。
• Biaryl formation using the suzuki protocol: Considerations of base, halide, and protecting group.
  作者：John W. Benbow、Bonnie L. Martinez

  DOI：10.1016/s0040-4039(96)02065-5

  日期：1996.12

  The generation of aryl anions prior to quenching with a trialkyl borate has been shown to be sensitive to the composition of the aryl substrate. Aryl iodides containing remote benzyl ether substituents undergo trans-metallation with sec-BuLi to cleanly give the desired aryl anions whereas the corresponding bromides afford appreciable quantities of dianionic intermediates. The arylboronic acids derived from alkylation of these anions subsequently undergo a palladium mediated coupling with aryl halides to provide good yields of the desired biaryls. Copyright (C) 1996 Elsevier Science Ltd.