(E)-3-(3,3-dimethyl-4-oxo-pentylidene)dihydrofuran-2(3H)-one | 643754-12-5

• 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: (E)-3-(3,3-dimethyl-4-oxo-pentylidene)dihydrofuran-2(3H)-one
• 英文别名: 3-(3,3-dimethyl-4-oxo-pentylidene)-dihydro-furan-2-one；(3E)-3-(3,3-dimethyl-4-oxopentylidene)oxolan-2-one
• CAS: 643754-12-5
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: YIPLXXRWLRFCDA-RUDMXATFSA-N

物化性质

• 沸点：
  353.7±25.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,3-dimethyl-4-oxo-pentylidene)dihydrofuran-2(3H)-one 在 六甲基磷酰三胺 、 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到2-vinyl-γ-butyrolactone
  参考文献：
  名称：

  Samarium(II)-Mediated Reactions of γ,δ-Unsaturated Ketones. Cyclization and Fragmentation Processes

  摘要：

  [GRAPHICS]On treatment with samarium(II) iodide, gamma,delta-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.

  DOI：

  10.1021/ol0260472
• 作为产物：
  描述：

  Alpha,Alpha-二甲基-γ-丁内酯 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 (E)-3-(3,3-dimethyl-4-oxo-pentylidene)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Samarium(II)-Mediated Reactions of γ,δ-Unsaturated Ketones. Cyclization and Fragmentation Processes

  摘要：

  [GRAPHICS]On treatment with samarium(II) iodide, gamma,delta-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.

  DOI：

  10.1021/ol0260472

文献信息

• Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol Cosolvent
  作者：Thomas K. Hutton、Kenneth W. Muir、David J. Procter

  DOI：10.1021/ol0358399

  日期：2003.12.1

  undergo two very different stereoselective cyclization reactions mediated by samarium(II) iodide depending upon the alcohol cosolvent used in the reaction. Switching between an unprecedented aldol spirocyclization and a novel cyclobutanol-forming process can be achieved simply by changing the alcohol cosolvent from methanol to tert-butyl alcohol. [reaction: see text]

  根据反应中使用的醇助溶剂，γ-不饱和酮会经历由碘化sa（II）介导的两个非常不同的立体选择性环化反应。只需将醇助溶剂从甲醇更改为叔丁醇，即可在前所未有的羟醛螺环化和新型环丁醇形成工艺之间进行切换。[反应：看文字]