9-Hydroxy-9-(3'-prop-1'-ynyl)spiro<5.5>undec-7-ene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-Hydroxy-9-(3'-prop-1'-ynyl)spiro<5.5>undec-7-ene
• 英文别名: 3-Hydroxy-3-prop-2-ynylspiro[5.5]undec-4-en-11-one
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: WYRYYKHTMXMHIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(羟基亚甲基)环己酮 在 氢氧化钾 、 甲烷磺酸 、 氢化铝 、 mercury dichloride 作用下， 反应 22.0h， 生成 9-Hydroxy-9-(3'-prop-1'-ynyl)spiro<5.5>undec-7-ene
  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.