(1S,2S,5R)-(3-hydroxy-1-propynylyl)-2-isopropyl-5-methylcyclohexanol | 530158-84-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,5R)-(3-hydroxy-1-propynylyl)-2-isopropyl-5-methylcyclohexanol
• CAS: 530158-84-0
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: AXEAWIZXGFPYNO-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,5R)-(3-hydroxy-1-propynylyl)-2-isopropyl-5-methylcyclohexanol 在 吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,2-双(二苯基膦)乙烷 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (1S,2S)-1,2-carbonyldioxy-2-[1-(4-methoxyphenoxy)vinyl]ethane-1-spiro-[(1'S,2'S,5'R)-2-isopropenyl-5-methyl]cyclohexane
  参考文献：
  名称：

  A Novel Methodology for the Synthesis of Cyclic Carbonates Based on the Palladium-Catalyzed Cascade Reaction of 4-Methoxycarbonyloxy-2-butyn-1-ols with Phenols, Involving a Novel Carbon Dioxide Elimination-Fixation Process

  摘要：

  A palladium-catalyzed CO2-recycling reaction has been developed. Reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, carried out in the presence of a palladium catalyst, produces phenoxy-substituted cyclic carbonates by way of a pathway involving a CO2 elimination-fixation. A variety of propargylic alcohols and phenols participate in these reactions which yield cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. Highly enantioselective reactions occur when (S)-BINAP is used as a ligand. Reaction of 4-phenoxycarbonyloxy2-butyn-1-ol in the presence of the palladium catalyst yields the corresponding cyclic carbonates via a three-component decomposition-reconstruction process.

  DOI：

  10.1021/ja0340681
• 作为产物：
  描述：

  (1S,2S,5R)-2-isopropyl-5-methyl-1-[3-(2H-tetrahydropyran-2-yloxy)-1-propynyl]cyclohexanol 在 甲醇 、 对甲苯磺酸 作用下， 反应 2.0h， 以91%的产率得到(1S,2S,5R)-(3-hydroxy-1-propynylyl)-2-isopropyl-5-methylcyclohexanol
  参考文献：
  名称：

  A Novel Methodology for the Synthesis of Cyclic Carbonates Based on the Palladium-Catalyzed Cascade Reaction of 4-Methoxycarbonyloxy-2-butyn-1-ols with Phenols, Involving a Novel Carbon Dioxide Elimination-Fixation Process

  摘要：

  A palladium-catalyzed CO2-recycling reaction has been developed. Reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, carried out in the presence of a palladium catalyst, produces phenoxy-substituted cyclic carbonates by way of a pathway involving a CO2 elimination-fixation. A variety of propargylic alcohols and phenols participate in these reactions which yield cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. Highly enantioselective reactions occur when (S)-BINAP is used as a ligand. Reaction of 4-phenoxycarbonyloxy2-butyn-1-ol in the presence of the palladium catalyst yields the corresponding cyclic carbonates via a three-component decomposition-reconstruction process.

  DOI：

  10.1021/ja0340681