tert-butyl N-[(1S)-1-[1-[(Z)-prop-1-enyl]pyrrol-2-yl]but-3-enyl]carbamate | 1073260-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tert-butyl N-[(1S)-1-[1-[(Z)-prop-1-enyl]pyrrol-2-yl]but-3-enyl]carbamate
• CAS: 1073260-74-8
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: TYJWBNPTTAGIIP-YLBKJLTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-1-[1-[(Z)-prop-1-enyl]pyrrol-2-yl]but-3-enyl]carbamate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以92%的产率得到tert-butyl N-[(8S)-7,8-dihydroindolizin-8-yl]carbamate
  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：

  (2S)-3-methyl-2-[[(1S)-1-[1-[(Z)-prop-1-enyl]pyrrol-2-yl]but-3-enyl]amino]butan-1-ol 、 二碳酸二叔丁酯 在 高碘酸 、 甲胺 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 四氢呋喃 为溶剂， 反应 4.0h， 以91%的产率得到tert-butyl N-[(1S)-1-[1-[(Z)-prop-1-enyl]pyrrol-2-yl]but-3-enyl]carbamate
  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.