1-(methoxyethenyl)cyclohexene | 1187319-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(methoxyethenyl)cyclohexene
• 英文别名: 1-(2-methoxyvinyl)cyclohex-1-ene；1-((E)-2-methoxyvinyl)cyclohex-1-ene；1-(2-methoxyethenyl)-cyclohexene；1-[(E)-2-methoxyethenyl]cyclohexene
• CAS: 1187319-12-5
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: OBSURRAANCYFMQ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲醇 、 1-乙炔基环己烷 在 dicarbonyl(5-phenyldipyrrinato)rhodium 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以85%的产率得到1-(methoxyethenyl)cyclohexene
  参考文献：
  名称：

  Dipyrrinato铑（I）配合物催化的末端炔烃的分子间加氢烷氧基化反应。

  摘要：

  An operationally simple and atom-economical method for the E-selective preparation of enol ethers is described. A novel dicarbonyl(S-phenyldipyrrinato)rhodium complex, 2, was prepared in four synthetic steps, characterized by X-ray crystallography and NMR spectroscopy, and then investigated as a catalyst for the intermolecular hydro-alkoxylation of terminal alkynes. Solvent and substrate studies were used to gain insight into the mechanism of the reaction. Cyclic voltammetry was also used to investigate the electronic properties of 2. The rhodium(I)-catalyzed intermolecular alkyne hydroalkoxylation reaction reported here mediates excellent substrate transformation with a high degree of E/Z selectivity which is opposite to that reported previously using alternative catalysts.

  DOI：

  10.1021/acs.organomet.5b00561

文献信息

• Nickel(II)-Catalyzed Borylation of Alkenyl Methyl Ethers via C–O Bond Cleavage
  作者：Xiaodong Qiu、Yangyang Li、Li Zhou、Peishan Chen、Fan Li、Yanan Zhang、Yong Ling

  DOI：10.1021/acs.orglett.0c02236

  日期：2020.8.21

  A new protocol has been developed for the borylation of conjugated alkenyl methyl ethers using B2Pin2 via C–O bond cleavage catalyzed by Ni(II). In this cross-coupling reaction, both E/Z isomers of alkenyl ethers are converted into (E)-alkenyl boronic esters with good reactivity. This transformation exhibits high chemoselectivity in the presence of competitive C–O bonds such as aryl ether, ester, amide

  已经开发了一种新的协议，用于使用B 2 Pin 2通过Ni（II）催化的C–O键断裂来使共轭烯基甲基醚硼化。在这种交叉偶联反应中，烯基醚的两个E / Z异构体都被转化为具有良好反应性的（E）-烯基硼酸酯。在竞争性的C–O键（例如芳基醚，酯，酰胺和硫醚基团）的存在下，这种转变表现出高化学选择性，从而为构建各种硼酸烯基酯提供了一种新方法。
• Rhodium-Catalyzed Anti-Markovnikov Intermolecular Hydroalkoxylation of Terminal Acetylenes
  作者：Masataka Kondo、Takuya Kochi、Fumitoshi Kakiuchi

  DOI：10.1021/ja1097385

  日期：2011.1.12

  We report here the first transition-metal-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes to give enol ethers in high yields without using bases. Arylacetylenes as well as alkenyl- and alkylacetylenes were coupled with aliphatic alcohols, and the products were obtained with high Z selectivity in most cases. Effective catalysts were 8-quinolinolato rhodium complexes, which are structurally simple but have been relatively unexplored as catalysts.
• Intermolecular Hydroalkoxylation of Terminal Alkynes Catalyzed by a Dipyrrinato Rhodium(I) Complex with Unusual Selectivity
  作者：Raphael H. Lam、D. Barney Walker、Matthew H. Tucker、Mark R. D. Gatus、Mohan Bhadbhade、Barbara A. Messerle

  DOI：10.1021/acs.organomet.5b00561

  日期：2015.9.14

  An operationally simple and atom-economical method for the E-selective preparation of enol ethers is described. A novel dicarbonyl(S-phenyldipyrrinato)rhodium complex, 2, was prepared in four synthetic steps, characterized by X-ray crystallography and NMR spectroscopy, and then investigated as a catalyst for the intermolecular hydro-alkoxylation of terminal alkynes. Solvent and substrate studies were used to gain insight into the mechanism of the reaction. Cyclic voltammetry was also used to investigate the electronic properties of 2. The rhodium(I)-catalyzed intermolecular alkyne hydroalkoxylation reaction reported here mediates excellent substrate transformation with a high degree of E/Z selectivity which is opposite to that reported previously using alternative catalysts.