1,4-Dioxadispiro[4.2.58.25]pentadec-6-en-9-one | 151813-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-Dioxadispiro[4.2.58.25]pentadec-6-en-9-one
• CAS: 151813-06-8
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: MLCPNNMONWKQCP-UHFFFAOYSA-N

物化性质

• 沸点：
  361.7±42.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-Dioxadispiro[4.2.58.25]pentadec-6-en-9-one 在 盐酸 、 偶氮二异丁腈 、 三正丁基氢锡 、 4-甲基苯磺酸吡啶 、 氢化铝 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 101.17h， 生成 Tricyclo<7.4.0.0^4,9>-1-hydroxy-3-methylidene-6-oxotridecane
  参考文献：
  名称：

  Stereocontrolled synthesis of angularly fused tricyclic systems by tin-mediated radical cyclization

  摘要：

  Two efficient pathways for the stereocontrolled synthesis of functionalized, angularly fused tricyclic carbocycles from readily available 2-formylcycloalkanones are described. Tricyclo[7.4.0.0(4,9)]tridecane 13, tricyclo[7.5.0.0(4,9)]tetradecane 16, and tricyclo[7.3.0.0(4,9)]dodecanes 20 and 21 were synthesized by means of path A. Path B is highly convergent, is 95% stereoselective, and leads to a tricyclo-[7.4.0.0(4,9)]tridecane skeleton 29.

  DOI：

  10.1021/jo00079a023
• 作为产物：
  描述：

  2-(羟基亚甲基)环己酮 在 氢氧化钾 、 甲烷磺酸 、 collidinium p-toluene sulfonate 作用下， 以 苯 为溶剂， 反应 29.0h， 生成 1,4-Dioxadispiro[4.2.58.25]pentadec-6-en-9-one
  参考文献：
  名称：

  Stereocontrolled synthesis of angularly fused tricyclic systems by tin-mediated radical cyclization

  摘要：

  Two efficient pathways for the stereocontrolled synthesis of functionalized, angularly fused tricyclic carbocycles from readily available 2-formylcycloalkanones are described. Tricyclo[7.4.0.0(4,9)]tridecane 13, tricyclo[7.5.0.0(4,9)]tetradecane 16, and tricyclo[7.3.0.0(4,9)]dodecanes 20 and 21 were synthesized by means of path A. Path B is highly convergent, is 95% stereoselective, and leads to a tricyclo-[7.4.0.0(4,9)]tridecane skeleton 29.

  DOI：

  10.1021/jo00079a023

文献信息

• Stereocontrolled synthesis of angularly fused tricyclic systems by tin-mediated radical cyclization
  作者：Selvasekaran Janardhanam、Ponnusamy Shanmugam、Krishnamoorthy Rajagopalan

  DOI：10.1021/jo00079a023

  日期：1993.12

  Two efficient pathways for the stereocontrolled synthesis of functionalized, angularly fused tricyclic carbocycles from readily available 2-formylcycloalkanones are described. Tricyclo[7.4.0.0(4,9)]tridecane 13, tricyclo[7.5.0.0(4,9)]tetradecane 16, and tricyclo[7.3.0.0(4,9)]dodecanes 20 and 21 were synthesized by means of path A. Path B is highly convergent, is 95% stereoselective, and leads to a tricyclo-[7.4.0.0(4,9)]tridecane skeleton 29.