4-[(1E)-pent-1-en-1-yl]-1-oxaspiro[4.4]non-3-en-2-one | 1403824-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-[(1E)-pent-1-en-1-yl]-1-oxaspiro[4.4]non-3-en-2-one
• 英文别名: 4-[(E)-pent-1-enyl]-1-oxaspiro[4.4]non-3-en-2-one
• CAS: 1403824-05-4
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: RAFQFLBCVSJKJW-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1-(hex-1-ynyl)cyclopentanol 在 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 N,N-二甲基苯胺 、 三乙胺 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 反应 2.42h， 生成 4-[(1E)-pent-1-en-1-yl]-1-oxaspiro[4.4]non-3-en-2-one 、 4-[(1Z)-pent-1-en-1-yl]-1-oxaspiro[4.4]non-3-en-2-one
  参考文献：
  名称：

  Synthesis of Bridged Polycyclic Ring Systems via Carbene Cascades Terminating in C–H Bond Insertion

  摘要：

  A carbene cascade reaction that constructs functionalized bridged bicyclic systems from alkynyl diazoesters is presented. The cascade proceeds through diazo decomposition, carbene/alkyne metathesis, and C H bond insertion. The diazoesters are easily synthesized from cyclic ketones. Substrate ring size and substitution patterns control the connectivity and diastereomeric preference found in the products.

  DOI：

  10.1021/ja308305z

文献信息

• Carbene cascades for the formation of bridged polycyclic rings
  作者：Santa Jansone-Popova、Phong Q. Le、Jeremy A. May

  DOI：10.1016/j.tet.2014.03.060

  日期：2014.7

  A general strategy to synthesize bridged polycyclic molecules is presented. The synthesis is accomplished via a cascade reaction initiated by rhodium carbene formation. Subsequent intramolecular reaction with an alkyne is then followed by a transannular C–H bond insertion. A rationale for prediction of the major structural isomer that is formed is described and applied to a wide variety of substrates

  提出了合成桥联多环分子的一般策略。合成通过铑卡宾形成引发的级联反应完成。随后，与炔烃的分子内反应随后是跨环的C–H键插入。描述了预测所形成的主要结构异构体的原理，并将其应用于多种底物。该原理基于基板中环系统的构象和立体电子方面的考虑。
• Synthesis of Bridged Polycyclic Ring Systems via Carbene Cascades Terminating in C–H Bond Insertion
  作者：Santa Jansone-Popova、Jeremy A. May

  DOI：10.1021/ja308305z

  日期：2012.10.31

  A carbene cascade reaction that constructs functionalized bridged bicyclic systems from alkynyl diazoesters is presented. The cascade proceeds through diazo decomposition, carbene/alkyne metathesis, and C H bond insertion. The diazoesters are easily synthesized from cyclic ketones. Substrate ring size and substitution patterns control the connectivity and diastereomeric preference found in the products.