1-(3-methoxycarbonyloxy-1-propynyl)cyclopentanol | 336104-94-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 1-(3-methoxycarbonyloxy-1-propynyl)cyclopentanol
• 英文别名: 3-(1-Hydroxycyclopentyl)prop-2-ynyl methyl carbonate
• CAS: 336104-94-0
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: DMVSKDOKWCFEML-UHFFFAOYSA-N

物化性质

• 沸点：
  299.7±33.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  萘酚 、 1-(3-methoxycarbonyloxy-1-propynyl)cyclopentanol 在 tris-(dibenzylideneacetone)dipalladium(0) 1,2-双(二苯基膦)乙烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以74%的产率得到1,2-carbonyldioxy-2-[1-(1-naphthoxy)vinyl]ethane-1-spirocyclopentane
  参考文献：
  名称：

  Palladium-Catalyzed Domino Reaction of 4-Methoxycarbonyloxy-2-butyn-1-ols with Phenols: A Novel Synthetic Method for Cyclic Carbonates with Recycling of CO2

  摘要：

  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.

  DOI：

  10.1002/1521-3773(20010202)40:3<616::aid-anie616>3.0.co;2-8
• 作为产物：
  描述：

  环戊酮 、 alkaline earth salt of/the/ methylsulfuric acid 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-(3-methoxycarbonyloxy-1-propynyl)cyclopentanol
  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