(2R,6S,E)-ethyl 2,6-dihydroxy-8-phenyloct-4-enoate | 1001652-56-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,6S,E)-ethyl 2,6-dihydroxy-8-phenyloct-4-enoate
• 英文别名: ethyl (E,2R,6S)-2,6-dihydroxy-8-phenyloct-4-enoate
• CAS: 1001652-56-7
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: MAOWUDLEPGUOHP-VOTDVEDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,6S,E)-ethyl 2,6-dihydroxy-8-phenyloct-4-enoate 、 三乙基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到(2R,6S,E)-ethyl 2-hydroxy-8-phenyl-6-(triethylsilyloxy)oct-4-enoate
  参考文献：
  名称：

  Concerning the Selective Protection of (Z)-1,5-syn-Ene-diols and (E)-1,5-anti-Ene-diols as Allylic Triethylsilyl Ethers

  摘要：

  Treatment of unsaturated 1,5-diols 2 with TES-CI (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with > 95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.

  DOI：

  10.1021/ol702588h
• 作为产物：
  描述：

  苯丙醛 、 乙醛酸乙酯 、 2-allenyl-1,3,2-dioxaborinane 在 diisopinocamphenylboron chloride 作用下， 以 乙醚 为溶剂， 反应 4.5h， 生成 (2R,6S,E)-ethyl 2,6-dihydroxy-8-phenyloct-4-enoate 、 (2S,6R,E)-ethyl 2,6-dihydroxy-8-phenyloct-4-enoate
  参考文献：
  名称：

  Concerning the Selective Protection of (Z)-1,5-syn-Ene-diols and (E)-1,5-anti-Ene-diols as Allylic Triethylsilyl Ethers

  摘要：

  Treatment of unsaturated 1,5-diols 2 with TES-CI (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with > 95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.

  DOI：

  10.1021/ol702588h

文献信息

• Concerning the Selective Protection of (<i>Z</i>)-1,5-<i>syn</i>-Ene-diols and (<i>E</i>)-1,5-<i>anti</i>-Ene-diols as Allylic Triethylsilyl Ethers
  作者：Jacqueline D. Hicks、Chan Woo Huh、Ashley D. Legg、William R. Roush

  DOI：10.1021/ol702588h

  日期：2007.12.1

  Treatment of unsaturated 1,5-diols 2 with TES-CI (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with > 95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.