4-(4-Phenyl-1-cyclohexenyl)-tetrahydro-furan-2-one | 133570-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-(4-Phenyl-1-cyclohexenyl)-tetrahydro-furan-2-one
• 英文别名: 4-(4-phenylcyclohexen-1-yl)oxolan-2-one
• CAS: 133570-25-9；133570-26-0
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: XRYBNWARLRETOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-phenylcyclohex-1-enyl trifluoromethanesulfonate 在 palladium diacetate Celite 、 苄基三乙基氯化铵 、 potassium carbonate 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.5h， 生成 4-(4-Phenyl-1-cyclohexenyl)-tetrahydro-furan-2-one
  参考文献：
  名称：

  β-Vinyl-γ-butyrolactones via the palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol

  摘要：

  The palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol affords beta-vinyl-gamma-butyrolactols (4-vinyl-2-hydroxy-tetrahydrofurans) which are converted into the corresponding beta-vinyl-gamma-butyrolactones by a smooth oxidation with Ag2CO3 on celite. Preparation of beta-substituted-gamma-butyrolactones can be performed without the isolation of the intermediate gamma-butyrolactols, thus simplifying the procedure and usually with higher overall yields. The outcome of the palladium-catalysed formation of beta-substituted-gamma-butyrolactols strongly depends on the nature of the added base. Best results are obtained by using NaHCO3 or K2CO3 in the presence of n-Bu4NCl or TEBA.

  DOI：

  10.1016/s0040-4020(01)86427-9

文献信息

• ARCADI, A.;BERNOCCHI, E.;CACCHI, S.;RARINELLI, F., TETRAHEDRON, 47,(1991) N, C. 1525-1540
  作者：ARCADI, A.、BERNOCCHI, E.、CACCHI, S.、RARINELLI, F.

  DOI：——

  日期：——
• β-Vinyl-γ-butyrolactones via the palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol
  作者：A Arcadi、E Bernocchi、S Cacchi、F Marinelli

  DOI：10.1016/s0040-4020(01)86427-9

  日期：1991.1

  The palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol affords beta-vinyl-gamma-butyrolactols (4-vinyl-2-hydroxy-tetrahydrofurans) which are converted into the corresponding beta-vinyl-gamma-butyrolactones by a smooth oxidation with Ag2CO3 on celite. Preparation of beta-substituted-gamma-butyrolactones can be performed without the isolation of the intermediate gamma-butyrolactols, thus simplifying the procedure and usually with higher overall yields. The outcome of the palladium-catalysed formation of beta-substituted-gamma-butyrolactols strongly depends on the nature of the added base. Best results are obtained by using NaHCO3 or K2CO3 in the presence of n-Bu4NCl or TEBA.