(2S)-3-methyl-2-[(1-prop-2-enylpyrrol-2-yl)methylideneamino]butan-1-ol | 1073260-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (2S)-3-methyl-2-[(1-prop-2-enylpyrrol-2-yl)methylideneamino]butan-1-ol
• CAS: 1073260-55-5
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: CTSBBEJWXFVUKR-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-3-methyl-2-[(1-prop-2-enylpyrrol-2-yl)methylideneamino]butan-1-ol 、 氯丙烯镁 在 水 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以92%的产率得到(2S)-3-methyl-2-[[(1S)-1-[1-[(Z)-prop-1-enyl]pyrrol-2-yl]but-3-enyl]amino]butan-1-ol
  参考文献：
  名称：

  Asymmetric Synthesis of 8-Aminoindolizidine from Chiral 2-Pyrroleimines

  摘要：

  1-Allyl-2-pyrroleimines obtained from (S)-valinol and (S)-phenylglycinol underwent highly diastereoselective addition of allylmagnesium chloride, used in excess amounts. to give the corresponding secondary amines with concomitant allyl to (Z)-1-propenyl isomerization of the 1-pyrrole substituent. Transformation of the 2-amino alcohol moiety to an oxazolidinone, or its cleavage and subsequent N-protection, followed by ring-closing metathesis of the two alkene groups gave the unsaturated bicyclic compound. Full hydrogenation of the alkene function and the aromatic rings afforded the indolizidine derivative as a mixture of two or three diastereomers with a ratio which was dependent on the nature of both the N-substituent and the catalyst. The two prevalent diastereomers were isolated, and their configuration was determined by X-ray crystallographic analysis.

  DOI：

  10.1021/jo8014598
• 作为产物：
  描述：

  L-缬氨醇 、 N-allylpyrrole-2-carboxaldehyde 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(2S)-3-methyl-2-[(1-prop-2-enylpyrrol-2-yl)methylideneamino]butan-1-ol
  参考文献：
  名称：

  Asymmetric Synthesis of 8-Aminoindolizidine from Chiral 2-Pyrroleimines

  摘要：

  1-Allyl-2-pyrroleimines obtained from (S)-valinol and (S)-phenylglycinol underwent highly diastereoselective addition of allylmagnesium chloride, used in excess amounts. to give the corresponding secondary amines with concomitant allyl to (Z)-1-propenyl isomerization of the 1-pyrrole substituent. Transformation of the 2-amino alcohol moiety to an oxazolidinone, or its cleavage and subsequent N-protection, followed by ring-closing metathesis of the two alkene groups gave the unsaturated bicyclic compound. Full hydrogenation of the alkene function and the aromatic rings afforded the indolizidine derivative as a mixture of two or three diastereomers with a ratio which was dependent on the nature of both the N-substituent and the catalyst. The two prevalent diastereomers were isolated, and their configuration was determined by X-ray crystallographic analysis.

  DOI：

  10.1021/jo8014598

文献信息

• Asymmetric Synthesis of 8-Aminoindolizidine from Chiral 2-Pyrroleimines
  作者：Vincenzo Giulio Albano、Andrea Gualandi、Magda Monari、Diego Savoia

  DOI：10.1021/jo8014598

  日期：2008.11.7

  1-Allyl-2-pyrroleimines obtained from (S)-valinol and (S)-phenylglycinol underwent highly diastereoselective addition of allylmagnesium chloride, used in excess amounts. to give the corresponding secondary amines with concomitant allyl to (Z)-1-propenyl isomerization of the 1-pyrrole substituent. Transformation of the 2-amino alcohol moiety to an oxazolidinone, or its cleavage and subsequent N-protection, followed by ring-closing metathesis of the two alkene groups gave the unsaturated bicyclic compound. Full hydrogenation of the alkene function and the aromatic rings afforded the indolizidine derivative as a mixture of two or three diastereomers with a ratio which was dependent on the nature of both the N-substituent and the catalyst. The two prevalent diastereomers were isolated, and their configuration was determined by X-ray crystallographic analysis.