N-(4-methoxybenzyl)-L-prolinol acrylate | 854917-82-1

• 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: N-(4-methoxybenzyl)-L-prolinol acrylate
• 英文别名: [(2S)-1-[(4-methoxyphenyl)methyl]pyrrolidin-2-yl]methyl prop-2-enoate
• CAS: 854917-82-1
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: KKKGKVWDRJHYJO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzyl)-L-prolinol acrylate 、 环戊二烯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-(4-methoxy-benzyl)-pyrrolidin-2-ylmethyl ester
  参考文献：
  名称：

  Exploiting π-shielding interactions: a highly selective chiral auxiliary derived from a biogenic building block

  摘要：

  A chiral auxiliary template, designed on the basis of pi-shielding capability has been prepared from readily available L-proline. Cycloaddition to an acrylate derivative gave high endo preference, and diastereoselectivity as high as 99% was attainable. The electronic factors contributing to selectivity were probed, and the technology successfully applied to a polymer supported variant. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.058
• 作为产物：
  描述：

  L-脯氨酸 在 lithium aluminium tetrahydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(4-methoxybenzyl)-L-prolinol acrylate
  参考文献：
  名称：

  Exploiting π-shielding interactions: a highly selective chiral auxiliary derived from a biogenic building block

  摘要：

  A chiral auxiliary template, designed on the basis of pi-shielding capability has been prepared from readily available L-proline. Cycloaddition to an acrylate derivative gave high endo preference, and diastereoselectivity as high as 99% was attainable. The electronic factors contributing to selectivity were probed, and the technology successfully applied to a polymer supported variant. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.058

文献信息

• Exploiting π shielding interactions of η6 arene chromium (0) complexes: New auxiliaries derived from the biogenic chiral pool
  作者：Jane Li、Longfei Xie、Mustafa Guzel、Steven B. Heaton、Dong Ma、Amy E. Kallmerten、Graham B. Jones

  DOI：10.1016/j.jorganchem.2007.09.005

  日期：2007.11

  A family of highly selective chiral auxiliaries containing arene chromium (0) complexes has been prepared using biogenic precursors from the chiral pool. The systems, derived from isomannide, prolinol, and xylofuranose were applied to the asymmetric Diels–Alder reaction of derived acrylate esters. Factors influencing stereoselectivity with the auxiliaries have been investigated and delineated including

  使用手性库中的生物前体制备了一系列含有芳烃铬（0）配合物的高选择性手性助剂。衍生自异甘露糖苷，脯氨醇和木呋喃糖的体系应用于衍生的丙烯酸酯的不对称Diels-Alder反应。已经研究并描述了影响助剂立体选择性的因素，包括混合配体对铬（0）配合物的影响。在最佳条件下，与环戊二烯进行环加成时，助剂的ee> 95％，exo：endo比率为98：2 。