(1S,2S,3Z)-3-(carbomethoxymethylene)-2-(formylmethyl)-2-methyl-1-cyclopentyl methyl ether | 147409-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3Z)-3-(carbomethoxymethylene)-2-(formylmethyl)-2-methyl-1-cyclopentyl methyl ether
• 英文别名: methyl (2Z)-2-[(2S,3S)-3-methoxy-2-methyl-2-(2-oxoethyl)cyclopentylidene]acetate
• CAS: 147409-92-5
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: PHBAGBLOKSHLIJ-JDQIMWGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3Z)-3-(carbomethoxymethylene)-2-(formylmethyl)-2-methyl-1-cyclopentyl methyl ether 在 RhCl(PPh₃)3 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以75%的产率得到(1S,3Z)-3-(carbomethoxymethylene)-1-methoxy-2,2-dimethylcyclopentane
  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：

  (1(S),7a(S))-1-methoxy-7a-methyl-7,7a-dihydro-5(6H)-indanone 在 potassium cyanide 、 sodium periodate 作用下， 以 乙醚 、 乙醇 、 水 、 苯 为溶剂， 反应 68.0h， 生成 (1S,2S,3Z)-3-(carbomethoxymethylene)-2-(formylmethyl)-2-methyl-1-cyclopentyl methyl ether
  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.