3-methylene-1-cyclodecanone | 194277-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methylene-1-cyclodecanone
• 英文别名: 3-Methylidenecyclodecan-1-one
• CAS: 194277-60-6
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: XLUZQDPTXAWIOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methylene-1-cyclodecanone 在 敌草腈 作用下， 以 甲苯 为溶剂， 反应 288.0h， 生成 (E)-3-methyl-2-cyclodecenone
  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
• 作为产物：
  描述：

  (E)-3-(methoxycarbonyl)cyclodec-3-enone 在 lithium aluminium tetrahydride 、 乙醇 、 水 、 4-甲基苯磺酸吡啶 、 三溴化磷 、 对甲苯磺酸 作用下， 以 乙醚 、 丙酮 、 甲苯 为溶剂， 反应 39.83h， 生成 3-methylene-1-cyclodecanone
  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

• （Ｅ）−３−メチル−２−シクロアルケノン化合物、３−ハロ−３−メチルシクロアルカノン化合物および（Ｒ）−３−メチルシクロアルカノン化合物の製造方法
  申请人：国立大学法人 新潟大学

  公开号：JP2018087184A

  公开（公告）日：2018-06-07

  【課題】新規の（Ｅ）−３−メチル−２−シクロアルケノン化合物および３−ハロ−３−メチルシクロアルカノン化合物を提供すること、また、（Ｒ）−３−メチルシクロアルカノン化合物を効率よく製造することができる製造方法を提供すること。【解決手段】本発明の（Ｅ）−３−メチル−２−シクロアルケノン化合物は、下記式（１）で示される化学構造を有することを特徴とする。【化１】（式（１）中のｎは１〜５、７または８の整数である。）【選択図】なし

  本发明提供了新的（E）-3-甲基-2-环己烯酮化合物和3-卤代-3-甲基环己烷酮化合物，并提供了一种能够高效制备（R）-3-甲基环己烷酮化合物的制备方法。本发明所述的（E）-3-甲基-2-环己烯酮化合物具有下式（1）所示的化学结构，其中n是1至5、7或8的整数。【化1】。
• 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.