(E)-1-(hex-2-en-1-yloxy)-3,5-dimethylbenzene | 1267551-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-(hex-2-en-1-yloxy)-3,5-dimethylbenzene
• CAS: 1267551-48-3
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: RKMOXRHXKQTOGE-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(hex-2-en-1-yloxy)-3,5-dimethylbenzene 、 联硼酸频那醇酯 在 rac-[CuCl(C₁₀H₆N₃(phenyl)2C₆H₂(CH₃)2C(CH₃)3)] NaOC(CH₃)3 、 CH₃OH 作用下， 以 乙醚 为溶剂， 以86%的产率得到(S)-2-(hex-1-en-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Stereoconvergent Synthesis of Chiral Allylboronates from an E/Z Mixture of Allylic Aryl Ethers Using a 6-NHC−Cu(I) Catalyst

  摘要：

  We present a 6-NHC-Cu(I) complex that provides alpha-substituted allylboronates using allylic aryl ether substrates. The method was discovered by comparison of the chemoselectivities exhibited by complexes 1a, 1b, 2, and 3. We observed that 1a preferentially reacts with electron-rich alkenes over electron-deficient alkenes. Development of an asymmetric method revealed that 1b reacts with both the E and Z isomers to provide the same absolute configuration without showing E-Z isomerization. This stereoconvergent reaction occurs with high yields (av 86%), high S(N)2` selectivity (> 99:1), and high ee (av 94%) and exhibits wide functional-group tolerance using pure E or Z isomer or E/Z alkene mixtures. The stereoconvergent feature enables the use of many different olefination strategies for substrate production, including cross-metathesis. Chiral allylboronates could be purified by silica gel chromatography and stored in the freezer without decomposition.

  DOI：

  10.1021/ja1112518
• 作为产物：
  描述：

  反式-2-已烯-1-醇 、 1,3-二甲基-5-碘苯 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以95%的产率得到(E)-1-(hex-2-en-1-yloxy)-3,5-dimethylbenzene
  参考文献：
  名称：

  Stereoconvergent Synthesis of Chiral Allylboronates from an E/Z Mixture of Allylic Aryl Ethers Using a 6-NHC−Cu(I) Catalyst

  摘要：

  We present a 6-NHC-Cu(I) complex that provides alpha-substituted allylboronates using allylic aryl ether substrates. The method was discovered by comparison of the chemoselectivities exhibited by complexes 1a, 1b, 2, and 3. We observed that 1a preferentially reacts with electron-rich alkenes over electron-deficient alkenes. Development of an asymmetric method revealed that 1b reacts with both the E and Z isomers to provide the same absolute configuration without showing E-Z isomerization. This stereoconvergent reaction occurs with high yields (av 86%), high S(N)2` selectivity (> 99:1), and high ee (av 94%) and exhibits wide functional-group tolerance using pure E or Z isomer or E/Z alkene mixtures. The stereoconvergent feature enables the use of many different olefination strategies for substrate production, including cross-metathesis. Chiral allylboronates could be purified by silica gel chromatography and stored in the freezer without decomposition.

  DOI：

  10.1021/ja1112518