1,1-bis(methoxycarbonyl)-2-(5',5'-tetramethylene-1',3',4'-pentatrien-2'-yl)cyclopropane | 1094602-81-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,1-bis(methoxycarbonyl)-2-(5',5'-tetramethylene-1',3',4'-pentatrien-2'-yl)cyclopropane
• CAS: 1094602-81-9
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: RUAUBKSZHLVFMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 1,1-bis(methoxycarbonyl)-2-(5',5'-tetramethylene-1',3',4'-pentatrien-2'-yl)cyclopropane 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以82%的产率得到4-(2',2'-bis(methoxycarbonyl)cyclopropyl)-2-(cyclopentylidene)cyclopent-3-enone
  参考文献：
  名称：

  Palladium-Catalyzed Regioselective Cyclopropanating Allenylation of (2,3-Butadienyl)malonates with Propargylic Carbonates and Their Application to Synthesize Cyclopentenones

  摘要：

  An efficient and highly regioselective route to synthesize polysubstituted 1,3,4-alkatrien-2-yl cyclopropane derivatives via Pd(0)-catalyzed highly regioselective coupling cyclization of (2,3-butadienyl)malonate or bis(phenylsulfonyl)methane with propargylic carbonates was reported. The reaction proceeded smoothly under neutral conditions to afford the products in 73-96% yields. The products may be efficiently converted to cyclopentenone derivatives via a catalytic Pauson-Khand reaction under ambient conditions.

  DOI：

  10.1021/ol802465k
• 作为产物：
  描述：

  methyl 1,1-tetramethyleneprop-2-ynyl carbonate 、 dimethyl 2,3-butadienylmalonate 在 四(三苯基膦)钯 、 四丁基碘化铵 作用下， 以 乙腈 为溶剂， 以75%的产率得到1,1-bis(methoxycarbonyl)-2-(5',5'-tetramethylene-1',3',4'-pentatrien-2'-yl)cyclopropane
  参考文献：
  名称：

  Palladium-Catalyzed Regioselective Cyclopropanating Allenylation of (2,3-Butadienyl)malonates with Propargylic Carbonates and Their Application to Synthesize Cyclopentenones

  摘要：

  An efficient and highly regioselective route to synthesize polysubstituted 1,3,4-alkatrien-2-yl cyclopropane derivatives via Pd(0)-catalyzed highly regioselective coupling cyclization of (2,3-butadienyl)malonate or bis(phenylsulfonyl)methane with propargylic carbonates was reported. The reaction proceeded smoothly under neutral conditions to afford the products in 73-96% yields. The products may be efficiently converted to cyclopentenone derivatives via a catalytic Pauson-Khand reaction under ambient conditions.

  DOI：

  10.1021/ol802465k