(1RS,2RS)-1,2-carbonyldioxy-2-[1-(4-methoxyphenoxy)vinyl]ethane-1-spiro-[(1'RS,2'RS)-2-phenyl]cyclohexane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1RS,2RS)-1,2-carbonyldioxy-2-[1-(4-methoxyphenoxy)vinyl]ethane-1-spiro-[(1'RS,2'RS)-2-phenyl]cyclohexane
• 英文别名: (4R,5R,6R)-4-[1-(4-methoxyphenoxy)ethenyl]-6-phenyl-1,3-dioxaspiro[4.5]decan-2-one
• 化学式: C₂₃H₂₄O₅
• 分子量: 380.441
• InChiKey: QFQDVMCJVSBCRU-MQSCRBSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-苯基环己酮 在 吡啶 、 甲醇 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 正丁基锂 、 四甲基乙二胺 、 对甲苯磺酸 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 (1RS,2RS)-1,2-carbonyldioxy-2-[1-(4-methoxyphenoxy)vinyl]ethane-1-spiro-[(1'RS,2'RS)-2-phenyl]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

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.