1,1-bis(2-cyclohexylethyl)-4-methoxycarbonyloxy-2-butyn-1-ol | 530158-18-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 1,1-bis(2-cyclohexylethyl)-4-methoxycarbonyloxy-2-butyn-1-ol
• 英文别名: [6-Cyclohexyl-4-(2-cyclohexylethyl)-4-hydroxyhex-2-ynyl] methyl carbonate
• CAS: 530158-18-0
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: DDEBDCGHZAMUOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯酚 、 1,1-bis(2-cyclohexylethyl)-4-methoxycarbonyloxy-2-butyn-1-ol 在 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 为溶剂， 以90%的产率得到1,2-carbonyldioxy-1,1-bis(2-cyclohexylethyl)-2-[1-(4-methoxyphenoxy)vinyl]ethane
  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：

  1,5-二环己基-3-戊酮 在 吡啶 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1,1-bis(2-cyclohexylethyl)-4-methoxycarbonyloxy-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

文献信息

• 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
  作者：Masahiro Yoshida、Mika Fujita、Tooru Ishii、Masataka Ihara

  DOI：10.1021/ja0340681

  日期：2003.4.1

  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.