(S)-2-((S,E)-1-(furan-2-yl)hexa-1,5-dien-3-ylamino)-3-phenylpropan-1-ol | 1246300-55-9

• 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: (S)-2-((S,E)-1-(furan-2-yl)hexa-1,5-dien-3-ylamino)-3-phenylpropan-1-ol
• 英文别名: (2S)-2-[[(1E,3S)-1-(furan-2-yl)hexa-1,5-dien-3-yl]amino]-3-phenylpropan-1-ol
• CAS: 1246300-55-9
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: PNJZCDDRIYPBGY-JWSDNSILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-((S,E)-1-(furan-2-yl)hexa-1,5-dien-3-ylamino)-3-phenylpropan-1-ol 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 N,N-二甲基丙烯基脲 、 正己烷 为溶剂， 生成 (R)-3-(furan-2-yl)hex-5-enal 、 (S)-3-(furan-2-yl)hex-5-enal
  参考文献：
  名称：

  Utilizing the Asymmetric Amino-Cope Rearrangement as a Novel Approach to Enantiomerically Enriched 3-Substituted Aldehydes

  摘要：

  We report the asymmetric amino-Cope rearrangement of some novel 3-amino-1,5-diene substrates to yield enantiomerically enriched 3-alkyl and 3-aryl aldehyde products. We have developed a system that gives excellent and comparable levels of product enantiomeric excess (ee) for both alkyl- and aryl-substituted products. Our results have implications for the control of the mechanistic pathway of the amino-Cope rearrangement and thus its potential utility in asymmetric synthesis.

  DOI：

  10.1080/00397910903318666
• 作为产物：
  描述：

  (S,2E)-2-((E)-3-(furan-2-yl)allylideneamino)-3-phenylpropan-1-ol 、 3-溴丙烯 在 碘 、 magnesium 、 水 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 18.0h， 以78%的产率得到(S)-2-((S,E)-1-(furan-2-yl)hexa-1,5-dien-3-ylamino)-3-phenylpropan-1-ol
  参考文献：
  名称：

  Utilizing the Asymmetric Amino-Cope Rearrangement as a Novel Approach to Enantiomerically Enriched 3-Substituted Aldehydes

  摘要：

  We report the asymmetric amino-Cope rearrangement of some novel 3-amino-1,5-diene substrates to yield enantiomerically enriched 3-alkyl and 3-aryl aldehyde products. We have developed a system that gives excellent and comparable levels of product enantiomeric excess (ee) for both alkyl- and aryl-substituted products. Our results have implications for the control of the mechanistic pathway of the amino-Cope rearrangement and thus its potential utility in asymmetric synthesis.

  DOI：

  10.1080/00397910903318666

文献信息

• Utilizing the Asymmetric Amino-Cope Rearrangement as a Novel Approach to Enantiomerically Enriched 3-Substituted Aldehydes
  作者：Steven M. Allin、Catarina Horro-Pita、Munira Essat、Ian Aspinall、Pritom Shah

  DOI：10.1080/00397910903318666

  日期：2010.8.16

  We report the asymmetric amino-Cope rearrangement of some novel 3-amino-1,5-diene substrates to yield enantiomerically enriched 3-alkyl and 3-aryl aldehyde products. We have developed a system that gives excellent and comparable levels of product enantiomeric excess (ee) for both alkyl- and aryl-substituted products. Our results have implications for the control of the mechanistic pathway of the amino-Cope rearrangement and thus its potential utility in asymmetric synthesis.