Methyl 5,5-dicyano-3-methylidene-1-(3-methylphenyl)cycloheptane-1-carboxylate | 1198581-65-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Methyl 5,5-dicyano-3-methylidene-1-(3-methylphenyl)cycloheptane-1-carboxylate
• 英文别名: methyl 5,5-dicyano-3-methylidene-1-(3-methylphenyl)cycloheptane-1-carboxylate
• CAS: 1198581-65-5
• 化学式: C₁₉H₂₀N₂O₂
• 分子量: 308.38
• InChiKey: YNDRTRRWBVTDDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  α-methoxycarbonyl-α-(3-methylphenyl)-γ-methylidene-δ-valerolactone 、 环丙烷-1,1-二腈 在 allyl(cyclopentadiene)palladium(II) 、 N,N-diethylbenzo[d][1,3,2]benzodioxaphosphepin-6-amine 作用下， 以 甲苯 为溶剂， 反应 12.08h， 以89%的产率得到Methyl 5,5-dicyano-3-methylidene-1-(3-methylphenyl)cycloheptane-1-carboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Decarboxylative [4 + 3] Cyclization of γ-Methylidene-δ-valerolactones with 1,1-Dicyanocyclopropanes

  摘要：

  A palladium-catalyzed decarboxylative [4 + 3] cyclization of gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanes has been developed to produce cycloheptane derivatives in a convergent manner. This method can be applied to the synthesis of azepanes by reacting with aziridines, and their asymmetric variants have also been described. In addition, selective ring-expansion reactions can be achieved for certain gamma-methylidene-delta-valerolactones to give nondecarboxylated nine-membered lactones.

  DOI：

  10.1021/ol902326s

文献信息

• Palladium-Catalyzed Decarboxylative [4 + 3] Cyclization of γ-Methylidene-δ-valerolactones with 1,1-Dicyanocyclopropanes
  作者：Ryo Shintani、Masataka Murakami、Takaoki Tsuji、Hideyuki Tanno、Tamio Hayashi

  DOI：10.1021/ol902326s

  日期：2009.12.17

  A palladium-catalyzed decarboxylative [4 + 3] cyclization of gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanes has been developed to produce cycloheptane derivatives in a convergent manner. This method can be applied to the synthesis of azepanes by reacting with aziridines, and their asymmetric variants have also been described. In addition, selective ring-expansion reactions can be achieved for certain gamma-methylidene-delta-valerolactones to give nondecarboxylated nine-membered lactones.