1-((benzyloxy)methyl)-3,5-dimethoxybenzene | 121682-89-1

• 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)methyl)-3,5-dimethoxybenzene
• 英文别名: 1-(benzyloxymethyl)-3,5-dimethoxybenzene；benzyl 3,5-dimethoxybenzyl ether；1,3-Dimethoxy-5-(phenylmethoxymethyl)benzene
• CAS: 121682-89-1
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: GKEAUGFSDKIWDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 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

• 作为产物：
  描述：

  potassium α-benzyloxymethyltrifluoroborate 、 1-溴-3,5-二甲氧基苯 在 dipotassium hydrogenphosphate 、 氯化镍二甲氧基乙烷 、 bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridyl]phenyl]iridium(1+); 2-(2-pyridyl)pyridine; hexafluorophosphate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以86%的产率得到1-((benzyloxy)methyl)-3,5-dimethoxybenzene
  参考文献：
  名称：

  Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers

  摘要：

  Single-electron transmetalation has emerged as an enabling paradigm for the cross-coupling of C-sp(3) hybridized organotrifluoroborates. Cross-coupling of alpha-alkoxymethyl-trifluoroborates with aryl and heteroaryl bromides has been demonstrated by employing dual catalysis with a combination of an iridium photoredox catalyst and a Ni cross-coupling catalyst. The resulting method enables the alkoxymethylation of diverse (hetero)arenes under mild, room-temperature conditions.

  DOI：

  10.1021/acs.orglett.5b01463

文献信息

• Preparation of Potassium Alkoxymethyltrifluoroborates and Their Cross-Coupling with Aryl Chlorides
  作者：Gary A. Molander、Belgin Canturk

  DOI：10.1021/ol800532p

  日期：2008.6.5

  A wide variety of alkoxymethyltrifluoroborate substrates were prepared via SN2 displacement of potassium bromomethyltrifluoroborate with various alkoxides in excellent yields. These alkoxymethyltrifluoroborates were effectively cross-coupled with several aryl chlorides. This method provides a unique dissonant disconnect that allows greater flexibility in the design of new and improved synthetic pathways

  通过用各种醇盐对溴甲基三氟硼酸钾进行 SN2 置换，以优异的产率制备了多种烷氧基甲基三氟硼酸盐底物。这些烷氧基甲基三氟硼酸盐与几种芳基氯有效地交叉偶联。这种方法提供了一种独特的不协调断开，允许在设计新的和改进的合成途径时具有更大的灵活性。
• Short synthesis of c-aryl-glucopyranosides of the papulacandin type
  作者：Richard R. Schmidt(rk)、Wendelin Frick

  DOI：10.1016/s0040-4020(01)86084-1

  日期：1988.1
• SCHMIDT, RICHARD R.;FRICK, WENDELIN, TETRAHEDRON, 44,(1988) N 23, C. 7163-7169
  作者：SCHMIDT, RICHARD R.、FRICK, WENDELIN

  DOI：——

  日期：——
• Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers
  作者：Idris Karakaya、David N. Primer、Gary A. Molander

  DOI：10.1021/acs.orglett.5b01463

  日期：2015.7.2

  Single-electron transmetalation has emerged as an enabling paradigm for the cross-coupling of C-sp(3) hybridized organotrifluoroborates. Cross-coupling of alpha-alkoxymethyl-trifluoroborates with aryl and heteroaryl bromides has been demonstrated by employing dual catalysis with a combination of an iridium photoredox catalyst and a Ni cross-coupling catalyst. The resulting method enables the alkoxymethylation of diverse (hetero)arenes under mild, room-temperature conditions.