(1S,2S)-2-hydroxymethyl-5-(1-methylethylidene)-N-[(1R)-(1-phenylethyl)]cyclopent-3-ene-1-carboxamide | 1373312-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S)-2-hydroxymethyl-5-(1-methylethylidene)-N-[(1R)-(1-phenylethyl)]cyclopent-3-ene-1-carboxamide
• CAS: 1373312-19-6
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: LBICMJQTKWOSKS-UNEWFSDZSA-N

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-hydroxymethyl-5-(1-methylethylidene)-N-[(1R)-(1-phenylethyl)]cyclopent-3-ene-1-carboxamide 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(3aS,6aS)-6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one
  参考文献：
  名称：

  Chiral blocks for the synthesis of cyclopentanoids from [2 + 2]-cycloadduct of dichloroketene and dimethylfulvene

  摘要：

  Opening of the alpha,alpha-dichlorocyclobutanone ring in the [2+2]-cycloadduct of dichloroketene and dimethylfulvene with (+)-alpha-methylbenzylamine gave diastereoisomeric 2-dichloromethyl-5-isopropylidene-N-(alpha-methylbenzyl)cyclopent-3-ene-1-carboxamides, and hydrolysis of the latter at the dichloromethyl group afforded the corresponding bicyclic aminals which can be readily separated by chromatography on silica gel. The subsequent removal of the alpha-methylbenzylamine fragment via reduction and hydrolysis resulted in the formation of enantiomerically pure (-)- and (+)-6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]-furan-1-ones.

  DOI：

  10.1134/s1070428012030190
• 作为产物：
  描述：

  (3aS,6aS)-3-hydroxy-6-(1-methylethylidene)-2-[(1R)-1-phenylethyl]-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以70%的产率得到(1S,2S)-2-hydroxymethyl-5-(1-methylethylidene)-N-[(1R)-(1-phenylethyl)]cyclopent-3-ene-1-carboxamide
  参考文献：
  名称：

  Chiral blocks for the synthesis of cyclopentanoids from [2 + 2]-cycloadduct of dichloroketene and dimethylfulvene

  摘要：

  Opening of the alpha,alpha-dichlorocyclobutanone ring in the [2+2]-cycloadduct of dichloroketene and dimethylfulvene with (+)-alpha-methylbenzylamine gave diastereoisomeric 2-dichloromethyl-5-isopropylidene-N-(alpha-methylbenzyl)cyclopent-3-ene-1-carboxamides, and hydrolysis of the latter at the dichloromethyl group afforded the corresponding bicyclic aminals which can be readily separated by chromatography on silica gel. The subsequent removal of the alpha-methylbenzylamine fragment via reduction and hydrolysis resulted in the formation of enantiomerically pure (-)- and (+)-6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]-furan-1-ones.

  DOI：

  10.1134/s1070428012030190