4-hydroxyspiro<5.5>undec-1-en-3-one | 147409-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxyspiro<5.5>undec-1-en-3-one
• 英文别名: 2-Hydroxyspiro[5.5]undec-4-en-3-one
• CAS: 147409-82-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: HOPYCLVOHQEEEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxyspiro<5.5>undec-1-en-3-one 在 sodium periodate 作用下， 以 水 为溶剂， 反应 12.0h， 生成 methyl (2Z)-3-(1'-(formylmethyl)-1'-cyclohexyl)acrylate
  参考文献：
  名称：

  Cleavage of unsaturated .alpha.-ketols to .omega.-oxo-.alpha.,.beta.-unsaturated acids

  摘要：

  Sodium periodate is a better reagent than sodium bismuthate, manganese dioxide, or lead tetraacetate for the cleavage of unsaturated alpha-ketols and affords omega-oxo-alpha,beta-unsaturated acids in good yield. The combination of this cleavage reaction and a rhodium(I)-mediated decarbonylation of omega-oxo-alpha,beta-unsaturated esters derived from polycyclic systems provided an enantioselective synthesis of cyclic systems bearing contiguous quaternary centers where one of the centers possessed gem-dimethyl groups.

  DOI：

  10.1021/jo00060a040
• 作为产物：
  描述：

  α'-4-acetoxyspiro<5.5>undec-1-en-3-one 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以80%的产率得到4-hydroxyspiro<5.5>undec-1-en-3-one
  参考文献：
  名称：

  Cleavage of unsaturated .alpha.-ketols to .omega.-oxo-.alpha.,.beta.-unsaturated acids

  摘要：

  Sodium periodate is a better reagent than sodium bismuthate, manganese dioxide, or lead tetraacetate for the cleavage of unsaturated alpha-ketols and affords omega-oxo-alpha,beta-unsaturated acids in good yield. The combination of this cleavage reaction and a rhodium(I)-mediated decarbonylation of omega-oxo-alpha,beta-unsaturated esters derived from polycyclic systems provided an enantioselective synthesis of cyclic systems bearing contiguous quaternary centers where one of the centers possessed gem-dimethyl groups.

  DOI：

  10.1021/jo00060a040

文献信息

• Floresca Rey, Kurihara Masaaki, Watt David S., Demir Ayhan, J. Org. Chem., 58 (1992) N 8, S 2196-2200
  作者：Floresca Rey, Kurihara Masaaki, Watt David S., Demir Ayhan

  DOI：——

  日期：——
• Cleavage of unsaturated .alpha.-ketols to .omega.-oxo-.alpha.,.beta.-unsaturated acids
  作者：Rey Floresca、Masaaki Kurihara、David S. Watt、Ayhan Demir

  DOI：10.1021/jo00060a040

  日期：1993.4

  Sodium periodate is a better reagent than sodium bismuthate, manganese dioxide, or lead tetraacetate for the cleavage of unsaturated alpha-ketols and affords omega-oxo-alpha,beta-unsaturated acids in good yield. The combination of this cleavage reaction and a rhodium(I)-mediated decarbonylation of omega-oxo-alpha,beta-unsaturated esters derived from polycyclic systems provided an enantioselective synthesis of cyclic systems bearing contiguous quaternary centers where one of the centers possessed gem-dimethyl groups.