1,1-bis(methoxycarbonyl)-2-(3'-methoxycarbonyl-5'-methyl-1',3',4'-hexatrien-2'-yl)cyclopropane | 1094602-86-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,1-bis(methoxycarbonyl)-2-(3'-methoxycarbonyl-5'-methyl-1',3',4'-hexatrien-2'-yl)cyclopropane
• CAS: 1094602-86-4
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: QYZKILHXQCNXRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Methyl 4-((methoxycarbonyl)oxy)-4-methylpent-2-ynoate 、 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96%的产率得到1,1-bis(methoxycarbonyl)-2-(3'-methoxycarbonyl-5'-methyl-1',3',4'-hexatrien-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

文献信息

• Palladium-Catalyzed Regioselective Cyclopropanating Allenylation of (2,3-Butadienyl)malonates with Propargylic Carbonates and Their Application to Synthesize Cyclopentenones
  作者：Wei Shu、Guochen Jia、Shengming Ma

  DOI：10.1021/ol802465k

  日期：2009.1.1

  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.