(Z)-α-(1-bromopentylidene)-β-(n-pentyl)-β-lactone | 849705-26-6

• 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: (Z)-α-(1-bromopentylidene)-β-(n-pentyl)-β-lactone
• 英文别名: (3Z)-3-(1-bromopentylidene)-4-pentyloxetan-2-one
• CAS: 849705-26-6
• 化学式: C₁₃H₂₁BrO₂
• 分子量: 289.213
• InChiKey: ZMAJFAPDJBYYLR-BENRWUELSA-N

物化性质

• 沸点：
  359.4±25.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-α-(1-bromopentylidene)-β-(n-pentyl)-β-lactone 、 苯硼酸 在 四(三苯基膦)钯 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 以93%的产率得到(Z)-α-(1-phenylpentylidene)-β-(n-pentyl)-β-lactone
  参考文献：
  名称：

  Studies on Pd(II)-Catalyzed Synthesis of (Z)-α-Haloalkylidene-β-lactones from Cyclocarbonylation of 2-Alkynols and the Subsequent Coupling Reactions

  摘要：

  A good regio- and stereoselectivity was observed for the PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 affording (Z)-alpha-chloroalkylidene-beta-lactons. The highly optically active (Z)-alpha-chloroalkylidene-beta-lactones could be easily prepared from the readily available optically active propargylic alcohols. The Pd(II)-catalyzed cyclocarbonylation of 2-alkynols with CuBr2 was also studied. Although the yields of (Z)-alpha-bromoalkylidene-beta-lactones were low, due to the relatively higher activity of the C-Br bond, the coupling reactions of (Z)-alpha-bromoalkylidene-beta-lactones were quite smooth to afford the corresponding products in high yields. A rationale for this reaction is discussed.

  DOI：

  10.1021/jo0480038
• 作为产物：
  描述：

  1-己炔 在 palladium diacetate 正丁基锂 、 对苯醌 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 苯 为溶剂， -78.0~30.0 ℃ 、2.03 MPa 条件下， 反应 2.0h， 生成 (Z)-α-(1-bromopentylidene)-β-(n-pentyl)-β-lactone
  参考文献：
  名称：

  Studies on Pd(II)-Catalyzed Synthesis of (Z)-α-Haloalkylidene-β-lactones from Cyclocarbonylation of 2-Alkynols and the Subsequent Coupling Reactions

  摘要：

  A good regio- and stereoselectivity was observed for the PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 affording (Z)-alpha-chloroalkylidene-beta-lactons. The highly optically active (Z)-alpha-chloroalkylidene-beta-lactones could be easily prepared from the readily available optically active propargylic alcohols. The Pd(II)-catalyzed cyclocarbonylation of 2-alkynols with CuBr2 was also studied. Although the yields of (Z)-alpha-bromoalkylidene-beta-lactones were low, due to the relatively higher activity of the C-Br bond, the coupling reactions of (Z)-alpha-bromoalkylidene-beta-lactones were quite smooth to afford the corresponding products in high yields. A rationale for this reaction is discussed.

  DOI：

  10.1021/jo0480038