1-[(E)-3-hydroxy-1-propenyl]cyclooctanol | 674368-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(E)-3-hydroxy-1-propenyl]cyclooctanol
• 英文别名: 1-[(E)-3-hydroxyprop-1-enyl]cyclooctan-1-ol
• CAS: 674368-14-0
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: FWIMVFUYYWWCBS-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(E)-3-hydroxy-1-propenyl]cyclooctanol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 、 1,1'-双(二苯基膦)二茂铁 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,2-carbonyldioxy-2-vinylethane-1-spirocyclooctane
  参考文献：
  名称：

  Palladium-Catalyzed Carbon Dioxide Elimination−Fixation Reaction of 4-Methoxycarbonyloxy-2-buten-1-ols

  摘要：

  A new type of palladium-catalyzed CO2 recycling reaction using allylic carbonates is described. Reaction of trans-4-methoxycarbonyloxy-2-buten-1-ols in the presence of a palladium catalyst produces cyclic carbonates having a vinyl group via a CO2 elimination-fixation process. A variety of allylic carbonates participate in the reaction giving cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. An enantiospecific reaction proceeds to give chiral cyclic carbonate when a chiral methyl-substituted substrate is subjected to the reaction conditions.

  DOI：

  10.1021/jo0353280
• 作为产物：
  描述：

  1-(3-hydroxy-1-propynyl)cyclooctanol 在 lithium aluminium tetrahydride 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以64%的产率得到1-[(E)-3-hydroxy-1-propenyl]cyclooctanol
  参考文献：
  名称：

  Palladium-Catalyzed Carbon Dioxide Elimination−Fixation Reaction of 4-Methoxycarbonyloxy-2-buten-1-ols

  摘要：

  A new type of palladium-catalyzed CO2 recycling reaction using allylic carbonates is described. Reaction of trans-4-methoxycarbonyloxy-2-buten-1-ols in the presence of a palladium catalyst produces cyclic carbonates having a vinyl group via a CO2 elimination-fixation process. A variety of allylic carbonates participate in the reaction giving cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. An enantiospecific reaction proceeds to give chiral cyclic carbonate when a chiral methyl-substituted substrate is subjected to the reaction conditions.

  DOI：

  10.1021/jo0353280