((hex-1-en-1-yloxy)methyl)benzene

• 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: ((hex-1-en-1-yloxy)methyl)benzene
• 英文别名: Hex-1-enoxymethylbenzene
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: AHTDLSYICTUIRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ((hex-1-en-1-yloxy)methyl)benzene 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 生成 (2E)-1-phenylhept-2-en-1-ol 、 (Z)-1-phenylhept-2-en-1-ol
  参考文献：
  名称：

  （Ž）α-Alkoxyacetoaldehydes的-选择性烯醇三氟甲磺酸：应用（合成ž经由交叉偶联反应） -烯丙基醇，[1,2] -Wittig重排

  摘要：

  α-烷氧基乙醛向相应的（Z）-乙烯基三氟甲磺酸酯的立体选择性转化是通过用三氟甲苯苯基酯和DBU处理而实现的。立体化学由“顺效应”解释，“顺效应”主要归因于σ→π*相互作用。通过过渡金属催化的交叉偶联反应和[1,2] -Wittig重排，将获得的β-烷氧基乙烯基三氟甲磺酸酯用于结构多样的（Z）-烯丙基醇的立体选择性合成。

  DOI：

  10.1021/acs.joc.5b00647
• 作为产物：
  描述：

  6-benzyloxy-1-hexene 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 四(3,5-二(三氟甲基)苯基)硼酸钠 、 (S)-2,2'-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl 作用下， 以 甲苯 为溶剂， 生成 ((hex-1-en-1-yloxy)methyl)benzene
  参考文献：
  名称：

  烯烃异构化的铱催化烯基醚的区域和对映选择性加氢芳基化

  摘要：

  烯基醚（如烯丙基和均烯丙基醚）的铱催化的C-H键活化产生高产率的相应加成产物，其中芳基被选择性地安装在烷氧基的α-碳原子上。该反应涉及烯基醚异构化为相应的1-烯基醚，然后进行区域和对映选择性的氢芳基化。

  DOI：

  10.1002/anie.201702286

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。
• High Diversity on Simple Substrates: 1,4-Dihalo-2-butenes and Other Difunctionalized Allylic Halides for Copper-Catalyzed SN2′ Reactions
  作者：Caroline A. Falciola、Alexandre Alexakis

  DOI：10.1002/chem.200801309

  日期：——

  Enantioselective allylic alkylation with an organomagnesium reagent catalyzed by copper thiophene carboxylate (CuTC) was carried out on difunctionalized substrates, such as commercially available 1,4-dichloro-2-butene and 1,4-dibromo-2-butene, and on similar compounds of higher substitution pattern of the olefin for the formation of all-carbon chiral quaternary centers. The high regioselectivity obtained

  对噻吩羧酸铜（CuTC）催化的有机镁试剂进行对映选择性烯丙基烷基化反应是在双官能化底物上进行的，例如市售的1,4-二氯-2-丁烯和1,4-二溴-2-丁烯，以及类似化合物全碳手性季中心形成烯烃的更高取代模式的研究。在整个反应过程中获得的高区域选择性有利于苯苯基格氏试剂的良好区域控制。其他双官能化的底物（烯丙基醚和烯丙醇）也经历了不对称的S（N）2'取代。
• Photocatalytic Umpolung of <i>N</i>- and <i>O</i>-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
  作者：Stephanie G. E. Amos、Stefano Nicolai、Jerome Waser

  DOI：10.1039/d0sc03655b

  日期：——

  organophotocatalytic 1,2-oxyalkynylation of ene-carbamates and enol ethers using Ethynyl BenziodoXolones (EBXs). 1-Alkynyl-1,2-amino alcohols and diols were obtained in up to 89% yield. Photocatalytic formation of radical cations led to Umpolung of the innate reactivity of the alkenes, enabling addition of a nucleophilic benzoate followed by radical alkynylation.

  我们报告使用乙炔基苯并基异戊二烯（EBXs）的烯氨基甲酸酯和烯醇醚的有机光催化1，2-氧炔基化。以高达89％的产率获得1-炔基-1,2-氨基醇和二醇。自由基阳离子的光催化形成导致烯烃固有反应性的发展，从而使得能够添加亲核苯甲酸酯，然后进行自由基炔基化。
• Iridium-Catalyzed Regio- and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization
  作者：Yusuke Ebe、Mitsuki Onoda、Takahiro Nishimura、Hideki Yorimitsu

  DOI：10.1002/anie.201702286

  日期：2017.5.8

  Iridium‐catalyzed hydroarylation of alkenyl ethers, such as allylic and homoallylic ethers, by C−H bond activation gave high yields of the corresponding addition products, where the aryl groups were selectively installed at the α‐carbon atom to the alkoxy group. The reaction involves an isomerization of the alkenyl ethers into the corresponding 1‐alkenyl ethers, which then undergo the regio‐ and enantioselective

  烯基醚（如烯丙基和均烯丙基醚）的铱催化的C-H键活化产生高产率的相应加成产物，其中芳基被选择性地安装在烷氧基的α-碳原子上。该反应涉及烯基醚异构化为相应的1-烯基醚，然后进行区域和对映选择性的氢芳基化。
• Copper-catalyzed formation of carbon heteroatom and carbon-carbon bonds
  申请人：Buchwald L. Stephen

  公开号：US20050215794A1

  公开（公告）日：2005-09-29

  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，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和酰胺或胺基团的氮原子之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和酰肼的氮原子之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和含氮杂环芳香族化合物（例如吲哚、吡唑和吲唑）的氮原子之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳和醇的氧原子之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子（例如烯醇酸根离子或马隆酸根离子）的反应物和苯基、杂环基或乙烯基卤化物或磺酸盐的活性碳之间形成碳-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易行。