4-hydroxy-1,1-bis(2-cyclohexylethyl)-2-butyn-1-ol | 530158-74-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-1,1-bis(2-cyclohexylethyl)-2-butyn-1-ol
• 英文别名: 6-cyclohexyl-4-(2-cyclohexylethyl)hex-2-yne-1,4-diol
• CAS: 530158-74-8
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: OLLOWRPZIQCLKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  467.7±20.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  4-hydroxy-1,1-bis(2-cyclohexylethyl)-2-butyn-1-ol 在 lithium aluminium tetrahydride 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以72%的产率得到(E)-4-hydroxy-1,1-bis(2-cyclohexylethyl)-2-butene-1-ol
  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：

  1,5-二环己基-3-戊酮 、 2-丙炔-1-醇 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以40%的产率得到4-hydroxy-1,1-bis(2-cyclohexylethyl)-2-butyn-1-ol
  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