1,2-carbonyldioxy-2-[1-(4-methylphenoxy)vinyl]ethane-1-spirocyclopentane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-carbonyldioxy-2-[1-(4-methylphenoxy)vinyl]ethane-1-spirocyclopentane
• 英文别名: 4-[1-(4-Methylphenoxy)ethenyl]-1,3-dioxaspiro[4.4]nonan-2-one；4-[1-(4-methylphenoxy)ethenyl]-1,3-dioxaspiro[4.4]nonan-2-one
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: RERFKOMTUHSPLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(3-羟基-1-丙炔-1-基)环戊醇 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 6.0h， 生成 1,2-carbonyldioxy-2-[1-(4-methylphenoxy)vinyl]ethane-1-spirocyclopentane
  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

• Palladium-Catalyzed Domino Reaction of 4-Methoxycarbonyloxy-2-butyn-1-ols with Phenols: A Novel Synthetic Method for Cyclic Carbonates with Recycling of CO2
  作者：Masahiro Yoshida、Masataka Ihara

  DOI：10.1002/1521-3773(20010202)40:3<616::aid-anie616>3.0.co;2-8

  日期：2001.2.2

  Refixation of the CO2 from a decarboxylation occurs in the palladium-catalyzed domino reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols. The reaction enables the construction of various cyclic carbonates [Eq. (1)] by efficient reincorporation of the CO2 molecule under mild conditions, and is thus a convenient and environmentally friendly method.
• 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.