dimethyl 4-isopropylidene-5-methylene-2-cycloheptene-1,1-dicarboxylate

• 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: dimethyl 4-isopropylidene-5-methylene-2-cycloheptene-1,1-dicarboxylate
• 英文别名: dimethyl 5-methylene-4-isopropylidene-2-cycloheptene-1,1-dicarboxylate；Dimethyl 5-methylidene-4-propan-2-ylidenecyclohept-2-ene-1,1-dicarboxylate；dimethyl 5-methylidene-4-propan-2-ylidenecyclohept-2-ene-1,1-dicarboxylate
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: FQMDHVXNXRXBQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 4-isopropylidene-5-methylene-2-cycloheptene-1,1-dicarboxylate 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以54%的产率得到dimethyl 5-methyl-4-isopropylidenecyclohepta-2,5-diene-1,1-dicarboxylate
  参考文献：
  名称：

  Carbon-Carbon Double-Bond Isomerization and Diels-Alder Reaction of Dimethyl 5-Methylene-4-isopropylidene-2-cycloheptene-1,1-dicarboxylate with Dienophiles

  摘要：

  三环化合物通过二甲基5-亚甲基-4-异丙基-2-环庚烯-1,1-二羧酸酯与二烯体在[RhCl(cod)₂]/dppe/AgOTf催化下进行碳-碳双键异构化-迪尔斯-阿尔德反应得到单一的非对映异构体。进一步实验证明了碳-碳双键的异构化。同时，当4-苯基-4H-1,2,4-三嗪-3,5-二酮作为二烯体时，发生了顺序的双重迪尔斯-阿尔德反应，而未发生碳-碳双键的异构化。

  DOI：

  10.1055/s-0029-1218574
• 作为产物：
  描述：

  dimethyl 2-(buta-2',3'-dienyl)-2-(4'-methylpenta-2',3'-dienyl)malonate 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 乙腈 为溶剂， 反应 17.5h， 以62%的产率得到dimethyl 4-isopropylidene-5-methylene-2-cycloheptene-1,1-dicarboxylate
  参考文献：
  名称：

  Observation of New Cycloisomerization Pattern of 1,5-Bisallenes. Catalyst and Substituent Effects

  摘要：

  In this paper a new cycloisomerization pattern of 1,5-bisallenes based on the catalyst and substituent effects has been reported. A range of seven-membered cross-conjugated trienes 7 would be obtained efficiently via the beta-H elimination and reductive elimination of the intermediates formed via cycloisomerization.

  DOI：

  10.1021/ol070632r

文献信息

• Observation of New Cycloisomerization Pattern of 1,5-Bisallenes. Catalyst and Substituent Effects
  作者：Ping Lu、Shengming Ma

  DOI：10.1021/ol070632r

  日期：2007.5.1

  In this paper a new cycloisomerization pattern of 1,5-bisallenes based on the catalyst and substituent effects has been reported. A range of seven-membered cross-conjugated trienes 7 would be obtained efficiently via the beta-H elimination and reductive elimination of the intermediates formed via cycloisomerization.
• Carbon-Carbon Double-Bond Isomerization and Diels-Alder Reaction of Dimethyl 5-Methylene-4-isopropylidene-2-cycloheptene-1,1-dicarboxylate with Dienophiles
  作者：Shengming Ma、Ping Lu、Jinqiang Kuang

  DOI：10.1055/s-0029-1218574

  日期：2010.1

  Tricyclic compounds were obtained as a single diastereomer via carbon-carbon double-bond isomerization-Diels-Alder reaction of dimethyl 5-methylene-4-isopropylidene-2-cycloheptene-1,1-dicarboxylate with dienophiles under the catalysis of [RhCl(cod)2]2/dppe/AgOTf. Further experiments provided the proof of isomerization of carbon-carbon double bond. Meanwhile a sequential double Diels-Alder reaction took place without carbon-carbon double-bond isomerization when 4-phenyl-4H-1,2,4-triazole-3,5-dione used as a dienophile.

  三环化合物通过二甲基5-亚甲基-4-异丙基-2-环庚烯-1,1-二羧酸酯与二烯体在[RhCl(cod)₂]/dppe/AgOTf催化下进行碳-碳双键异构化-迪尔斯-阿尔德反应得到单一的非对映异构体。进一步实验证明了碳-碳双键的异构化。同时，当4-苯基-4H-1,2,4-三嗪-3,5-二酮作为二烯体时，发生了顺序的双重迪尔斯-阿尔德反应，而未发生碳-碳双键的异构化。