(1,4-Dioxa-spiro[4.6]undec-7-en-7-yl)-methanol | 194277-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,4-Dioxa-spiro[4.6]undec-7-en-7-yl)-methanol
• 英文别名: 1,4-Dioxaspiro[4.6]undec-7-en-7-ylmethanol
• CAS: 194277-64-0
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: DEYPBIXUHJCYTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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-2-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
• 作为产物：
  描述：

  1-Cycloheptene-1-carboxylic acid, 6-oxo-, methyl ester 在 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 生成 (1,4-Dioxa-spiro[4.6]undec-7-en-7-yl)-methanol
  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

• 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.