2-(2,2-二甲氧基乙氧基)-1,3-二甲基苯 | 72138-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(2,2-二甲氧基乙氧基)-1,3-二甲基苯
• 英文名称: 2-(2,2-dimethoxyethoxy)-1,3-dimethylbenzene
• 英文别名: Benzene, 2-(2,2-dimethoxyethoxy)-1,3-dimethyl-
• CAS: 72138-91-1
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: FYQURTMVHVDCSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  烯丙基2,6-二甲基苯基醚 在 二甲基硫 、 对甲苯磺酸 、 臭氧 作用下， 以 甲醇 为溶剂， 生成 2-(2,2-二甲氧基乙氧基)-1,3-二甲基苯
  参考文献：
  名称：

  Ozonolysis of olefins VIII. Synthesis of phenoxyacetaldehydes by ozonolysis of allylphenylethers

  摘要：

  A new route for the preparation of a series of phenoxyacetaldehydes (2a-j) which are useful intermediates or products, is described. It starts from the easily available allylphenylethers 1a-j which are ozonized at - 40 degrees C and further treated with dimethylsulfide to give solutions of the corresponding phenoxyacetaldehydes 2a-j; these are purified by column chromatography. Reaction of 2a-j with 1-methyl-1-phenylhydrazine leads to the corresponding hydrazones 3a-c, 3e-g, 3i, and 3j. The aldehydes can also be transformed into the stable dimethylcetals 4a, 4e, 4h, and 4i by reaction with trimethyl orthoformate.

  DOI：

  10.1007/bf00807397

文献信息

• Palladium-Catalyzed C(sp³ )−H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group
  作者：Sahra St John-Campbell、Alex K. Ou、James A. Bull

  DOI：10.1002/chem.201804515

  日期：2018.12.3

  requires derivatization at nitrogen with a directing group. Transient directing groups (TDGs) permit C−H functionalization in a single operation, without needing these additional steps for directing group installation and removal. Here we report a palladium catalyzed γ‐C−H arylation of amines using catalytic amounts of alkyl acetals as transient activators (e.g. commercially available (2,2‐dimethoxyethoxy)benzene)

  由于胺与过渡金属催化剂的强烈络合，胺的 C−H 官能化是一个突出的挑战，因此通常需要用导向基团在氮上进行衍生化。瞬态定向基团 (TDG) 允许在单个操作中实现 CH 功能化，而不需要这些额外的步骤来安装和移除定向基团。在这里，我们报道了使用催化量的烷基缩醛作为瞬时活化剂（例如市售的（2,2-二甲氧基乙氧基）苯）的钯催化的胺的γ-C-H芳基化。这种简单的添加剂可以使胺与多种芳基碘化物发生芳基化。对新型 TDG 的关键结构特征进行了研究，证明了掩蔽的羰基和醚官能团的重要作用。详细的动力学 (RPKA) 和机制研究确定了所有试剂的顺序，并将环钯化确定为周转限制步骤。最后，报道了一种前所未有的非循环游离胺定向的芳基化产物的ε-环钯化反应。
• Ozonolysis of olefins VIII. Synthesis of phenoxyacetaldehydes by ozonolysis of allylphenylethers
  作者：W. Jellen、M. Mittelbach、H. Junek

  DOI：10.1007/bf00807397

  日期：1996.2

  A new route for the preparation of a series of phenoxyacetaldehydes (2a-j) which are useful intermediates or products, is described. It starts from the easily available allylphenylethers 1a-j which are ozonized at - 40 degrees C and further treated with dimethylsulfide to give solutions of the corresponding phenoxyacetaldehydes 2a-j; these are purified by column chromatography. Reaction of 2a-j with 1-methyl-1-phenylhydrazine leads to the corresponding hydrazones 3a-c, 3e-g, 3i, and 3j. The aldehydes can also be transformed into the stable dimethylcetals 4a, 4e, 4h, and 4i by reaction with trimethyl orthoformate.