(-)-(1S)-1-Ethyl-1,2,3,5,6,7-hexahydro-2-methylene-4H-inden-4-one | 131617-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(1S)-1-Ethyl-1,2,3,5,6,7-hexahydro-2-methylene-4H-inden-4-one
• 英文别名: (1S)-1-ethyl-2-methylidene-3,5,6,7-tetrahydro-1H-inden-4-one
• CAS: 131617-91-9
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: QRVJXLXNYBEBDH-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(1S)-1-Ethyl-1,2,3,5,6,7-hexahydro-2-methylene-4H-inden-4-one 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 21.0h， 生成 1-Ethyl-3,5,6,7-tetrahydro-2-methyl-4H-inden-4-one
  参考文献：
  名称：

  Manganese(III)-based asymmetric oxidative free-radical cyclization of unsaturated .beta.-keto sulfoxides

  摘要：

  beta-Keto sulfoxides and beta-keto sulfones can be used as substrates for Mn(III)- and Cu(II)-based oxidative free-radical cyclizations. The sulfoxide chiral center completely controls the stereochemistry of the cyclization. Oxidative cyclization of racemic sulfoxide 8 affords 13 as a single diastereomer. Oxidative cyclization of enantiomerically pure sulfoxide 20 gives 21 as a single enantiomer. The chiral auxiliary can be removed by oxidation with potassium peroxomonosulfate to give the sulfone followed by reduction with sodium amalgam to give bicyclo[3.2.1]octanone 23. Oxidative cyclization of 26 gives indanone 29, which spontaneously loses toluenesulfenic acid to give indenone 30.

  DOI：

  10.1021/jo00001a061
• 作为产物：
  描述：

  N-Methoxy-cis-octenamide 在 sodium hydroxide 、 copper diacetate 、 苄基三乙基氯化铵 、 potassium acetate 、 manganese triacetate 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 27.5h， 生成 (-)-(1S)-1-Ethyl-1,2,3,5,6,7-hexahydro-2-methylene-4H-inden-4-one
  参考文献：
  名称：

  Manganese(III)-based asymmetric oxidative free-radical cyclization of unsaturated .beta.-keto sulfoxides

  摘要：

  beta-Keto sulfoxides and beta-keto sulfones can be used as substrates for Mn(III)- and Cu(II)-based oxidative free-radical cyclizations. The sulfoxide chiral center completely controls the stereochemistry of the cyclization. Oxidative cyclization of racemic sulfoxide 8 affords 13 as a single diastereomer. Oxidative cyclization of enantiomerically pure sulfoxide 20 gives 21 as a single enantiomer. The chiral auxiliary can be removed by oxidation with potassium peroxomonosulfate to give the sulfone followed by reduction with sodium amalgam to give bicyclo[3.2.1]octanone 23. Oxidative cyclization of 26 gives indanone 29, which spontaneously loses toluenesulfenic acid to give indenone 30.

  DOI：

  10.1021/jo00001a061

文献信息

• SNIDER, BARRY B.;WAN, BARBARA YU-FONG;BUCKMAN, BRAD O.;FOXMAN, BRUCE M., J. ORG. CHEM., 56,(1991) N, C. 328-334
  作者：SNIDER, BARRY B.、WAN, BARBARA YU-FONG、BUCKMAN, BRAD O.、FOXMAN, BRUCE M.

  DOI：——

  日期：——