9-丙-2-炔基-1,4-二氧杂-二螺[4.2.4.2]十四碳-6-烯-9-醇 | 1027384-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 9-丙-2-炔基-1,4-二氧杂-二螺[4.2.4.2]十四碳-6-烯-9-醇
• 英文名称: 9-Prop-2-ynyl-1,4-dioxa-dispiro[4.2.4.2]tetradec-6-en-9-ol
• 英文别名: 4-Prop-2-ynyl-9,12-dioxadispiro[4.2.48.25]tetradec-13-en-4-ol
• CAS: 1027384-57-1
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: ZUIMXEQTDVTCLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-丙-2-炔基-1,4-二氧杂-二螺[4.2.4.2]十四碳-6-烯-9-醇 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 1-Hydroxy-1-(3'-prop-1'-ynyl)spiro<4.5>dec-6-ene-8-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
• 作为产物：
  描述：

  螺[4.5]癸-9-烯-4,8-二酮 在 collidinium p-toluene sulfonate 、 氢化铝 、 mercury dichloride 作用下， 以 苯 为溶剂， 反应 19.0h， 生成 9-丙-2-炔基-1,4-二氧杂-二螺[4.2.4.2]十四碳-6-烯-9-醇
  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.