3-甲基环庚-3-烯-1-酮 | 14525-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-甲基环庚-3-烯-1-酮
• 英文名称: 3-methylcyclohept-3-en-1-one
• CAS: 14525-96-3
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: MQEAASYWNDKGRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1,4-Dioxa-spiro[4.6]undec-7-en-7-yl)-methanol 在 lithium aluminium tetrahydride 、 水 、 4-甲基苯磺酸吡啶 、 三溴化磷 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 0.5h， 生成 3-甲基环庚-3-烯-1-酮
  参考文献：
  名称：

  Medium-Ring Systems. 6.¹ Synthesis and Isomerizations of Medium-Ring 3-Methylenecycloalkanones and 3-Methylcycloalkenones

  摘要：

  A series of 3-methylenecycloalkanones with ring sizes 7-10 has been prepared and subjected to base-catalyzed isomerization. Equilibrium between these exocyclic isomers and the corresponding 3-methyl-2-cycloalkenones and 3-methyl-3-cycloalkenones was reached in the 7- and 8-membered rings. The presence of the beta-methyl shifts these equilibria toward the Delta(2) isomer in each ring relative to the unsubstituted compounds and to compounds containing electron-withdrawing groups at the beta position. In the 9- and 10-membered rings, the Delta(2) isomers were isomerized to the Delta(3) isomers only with difficulty, and the reverse process could not be accomplished under the reaction conditions utilized. The ease of interconversion of the Delta(2) and Delta(3) isomers is directly related to the thermodynamic stability of planar conjugated dienes in medium ring carbocycles.

  DOI：

  10.1021/jo9705374

文献信息

• Carbocyclic ring expansion reactiuon VIA radical chain processes
  作者：Jack E. Baldwin、Robert M. Adlington、Jeremy Robertson

  DOI：10.1016/0040-4020(89)80003-1

  日期：1989.1
• A convenient regioselective synthesis of substituted cycloheptenones
  作者：Chwang Siek Pak、Sung Kee Kim

  DOI：10.1021/jo00293a051

  日期：1990.3
• BALDWIN, JACK E.;ADLINGTON, ROBERT M.;ROBERTSON, JEREMY, TETRAHEDRON, 45,(1989) N, C. 909-922
  作者：BALDWIN, JACK E.、ADLINGTON, ROBERT M.、ROBERTSON, JEREMY

  DOI：——

  日期：——
• PAK, CHWANG SIEK;KIM, SUNG KEE, J. ORG. CHEM., 55,(1990) N, C. 1954-1957
  作者：PAK, CHWANG SIEK、KIM, SUNG KEE

  DOI：——

  日期：——
• Medium-Ring Systems. 6.¹ Synthesis and Isomerizations of Medium-Ring 3-Methylenecycloalkanones and 3-Methylcycloalkenones
  作者：Philip Eskola、Jerry A. Hirsch

  DOI：10.1021/jo9705374

  日期：1997.8.1

  A series of 3-methylenecycloalkanones with ring sizes 7-10 has been prepared and subjected to base-catalyzed isomerization. Equilibrium between these exocyclic isomers and the corresponding 3-methyl-2-cycloalkenones and 3-methyl-3-cycloalkenones was reached in the 7- and 8-membered rings. The presence of the beta-methyl shifts these equilibria toward the Delta(2) isomer in each ring relative to the unsubstituted compounds and to compounds containing electron-withdrawing groups at the beta position. In the 9- and 10-membered rings, the Delta(2) isomers were isomerized to the Delta(3) isomers only with difficulty, and the reverse process could not be accomplished under the reaction conditions utilized. The ease of interconversion of the Delta(2) and Delta(3) isomers is directly related to the thermodynamic stability of planar conjugated dienes in medium ring carbocycles.