1-butoxy-3-methoxybenzene | 51241-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-butoxy-3-methoxybenzene
• CAS: 51241-32-8
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: WSKZNCFDZYXAON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  3-氰基苯甲酸 、 1-butoxy-3-methoxybenzene 、 、 盐酸 在 氯化亚砜 、 acid chloride 、 硝基苯 、 三氯化铝 、 ice 、 乙醚 、 magnesium sulfate 、 silica gel 作用下， 以 氯化亚砜 为溶剂， 反应 19.5h， 以to yield 3-(4-butoxy-2-hydroxybenzoyl)benzonitrile (1.8 g)的产率得到3-(4-Butoxy-2-hydroxybenzoyl)benzonitrile
  参考文献：
  名称：

  Alkylarylketo acids

  摘要：

  本发明涉及一种新型的烷基芳基酮羧酸和5-取代四唑，其化学式为##STR1##其中Z为芳基或结构为##STR2##的烷基；W为羧基或结合在Z的五位的四唑基；R.sub.1为C.sub.4-C.sub.12烷基（其中Z为芳基且X为氧原子）或C.sub.5-C.sub.12烷基（其中Z为烷基且X为键）；R.sub.2和R.sub.3分别独立地为氢、C.sub.1-C.sub.4烷基、羟基、C.sub.1-C.sub.4烷氧基、卤素、三卤甲基、硝基、氰基或C.sub.1-C.sub.4酰基；R.sub.4、R.sub.5、R.sub.6和R.sub.7分别独立地为氢或C.sub.1-C.sub.4烷基，或R.sub.4和R.sub.6或R.sub.5和R.sub.7可以结合形成碳环；X为氧原子或正、邻位的键；m为0、1或2；n为0或1。本发明还涉及这些化合物的无毒、药学上可接受的盐和羧酸酯。

  公开号：

  US05504244A1
• 作为产物：
  描述：

  1,3-二氟苯 在 N,N-二甲基丙烯基脲 、 potassium tert-butylate 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 24.0h， 生成 1-butoxy-3-methoxybenzene
  参考文献：
  名称：

  Novel Synthesis of Desymmetrized Resorcinol Derivatives:  Aryl Fluoride Displacement on Deactivated Substrates

  摘要：

  A short, high-yielding synthesis of differentially substituted resorcinol derivatives has been developed that utilizes 1,3difluorobenzene as the starting material and employs sequential nucleophilic aromatic substitution (SNAr) reactions to generate desymmetrized products. The scope and limitations of the second SNAr reaction on the deactivated 1-alkoxy-3-fluorobenzene intermediates have been investigated. This methodology has also been employed in the synthesis of desymmetrized catechol derivatives from 1,2difluorobenzene.

  DOI：

  10.1021/jo0523868

文献信息

• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• Synthesis of Aryl Ethers from Aromatic Carboxylic Acids
  作者：Lukas Gooßen、Sukalyan Bhadra、Wojciech Dzik

  DOI：10.1055/s-0033-1339470

  日期：——

  meta-substituted carboxylates are converted into para-substituted alkoxyarenes and vice versa. The combined processes provide a convenient synthetic entry to the important class of aromatic ethers from widely available carboxylic acids. A silver/copper bimetallic catalyst system promotes the decarboxylative Chan–Evans–Lam alkoxylation of ortho-substituted aromatic carboxylate salts with tetraalkyl orthosilicates

  摘要 银/铜双金属催化剂体系可促进原位取代的芳族羧酸盐与原硅酸四烷基酯或硼酸三芳基酯的脱羧化Chan-Evans-Lam烷氧基化反应。非邻位取代的羧酸盐通过邻-C-H-烷氧基化被烷氧基化，同时羧酸酯导向基团通过原脱羧作用被裂解。这样，间位取代的羧酸盐被转化为对位取代的烷氧基芳烃，反之亦然。组合的方法可以从广泛使用的羧酸中方便地合成进入重要类别的芳族醚。 银/铜双金属催化剂体系可促进原位取代的芳族羧酸盐与原硅酸四烷基酯或硼酸三芳基酯的脱羧化Chan-Evans-Lam烷氧基化反应。非邻位取代的羧酸盐通过邻-C-H-烷氧基化被烷氧基化，同时羧酸酯导向基团通过原脱羧作用被裂解。这样，间位取代的羧酸盐被转化为对位取代的烷氧基芳烃，反之亦然。组合的方法可以从广泛使用的羧酸中方便地合成进入重要类别的芳族醚。
• Oxalic Diamides and <i>tert</i>-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction
  作者：Zhixiang Chen、Yongwen Jiang、Li Zhang、Yinlong Guo、Dawei Ma

  DOI：10.1021/jacs.8b12142

  日期：2019.2.27

  A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic

  已经开发了一种用于制备烷基芳基醚的稳健实用的方案，该方案依赖于使用两种类型的配体来促进 Cu 催化的（杂）芳基卤化物的烷氧基化。反应范围非常适用于各种偶联伙伴，尤其是具有挑战性的仲醇和（杂）芳基氯。在与芳基氯化物和溴化物偶联的情况下，两个草酸二酰胺作为强大的配体。叔丁醇首先被证明是铜催化偶联反应的配体，导致芳基碘化物在室温下完成烷氧基化。此外，许多碳水化合物衍生物适用于该偶联反应，以 29-98% 的产率提供相应的碳水化合物-芳基醚。
• Copper-Catalyzed Coupling of Aryl Iodides with Aliphatic Alcohols
  作者：Martina Wolter、Gero Nordmann、Gabriel E. Job、Stephen L. Buchwald

  DOI：10.1021/ol025548k

  日期：2002.3.1

  and mild method for the coupling of aryl iodides and aliphatic alcohols that does not require the use of alkoxide bases is described. The reactions can be performed in neat alcohol. For more precious alcohols, the etherification was carried out in toluene as solvent using 2 equiv of alcohol. Additionally, the cross-coupling of an optically active benzylic alcohol with an unactivated aryl halide was demonstrated

  [反应：见正文]描述了一种简单而温和的偶联芳基碘化物和脂肪醇的方法，该方法不需要使用醇盐碱。反应可以在纯醇中进行。对于更珍贵的醇，醚化是在甲苯中作为溶剂，使用2当量的醇进行的。此外，光学活性的苯甲醇与未活化的芳基卤化物的交叉偶联被证明完全保留了构型。
• Synthesis of Aryl Ethers from Benzoates through Carboxylate-Directed CH-Activating Alkoxylation with Concomitant Protodecarboxylation
  作者：Sukalyan Bhadra、Wojciech I. Dzik、Lukas J. Gooßen

  DOI：10.1002/anie.201208755

  日期：2013.3.4

  copper/silver bimetallic catalyst system, aromatic carboxylate salts undergo ortho CH alkoxylation with concomitant loss of the carboxylate directing group in a protodecarboxylation step (see scheme, FG=functional group). This process provides a convenient synthetic access to the important class of aromatic ethers from widely available carboxylic acids.

  一个在其中的一种出：在一个铜/银双金属催化剂体系的存在下，芳族羧酸盐进行邻Ç  ħ烷氧基化伴随羧酸引导组的损失在protodecarboxylation步骤（参见方案，FG =官能团）。该方法提供了从广泛可得的羧酸方便地合成重要种类的芳族醚的途径。