methyl trans-N-formyl-α'-(2,4,6-triethylphenyl)-L-prolinate | 891778-35-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl trans-N-formyl-α'-(2,4,6-triethylphenyl)-L-prolinate
• 英文别名: methyl trans-N-formyl-5-(2,4,6-triethylphenyl)-L-prolinate
• CAS: 891778-35-1
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: LVEPBKUNVFMZGI-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl trans-N-formyl-α'-(2,4,6-triethylphenyl)-L-prolinate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到trans-N-formyl-α'-(2,4,6-triethylphenyl)-L-proline
  参考文献：
  名称：

  New Efficient Organic Activators for Highly Enantioselective Reduction of Aromatic Ketones by Trichlorosilane

  摘要：

  Aryl ketones were reduced to the corresponding alcohols with excellent enantioselectivity (up to 99.7% ee) by Cl3SiH in the presence of a catalytic amount of N-formyl-alpha '-(2,4,6-triethylphenyl)-L-proline as an activator. Both carboxyl group at the alpha-position of the activator and 2,4,6-triethylphenyl group at the alpha '-position were critical for the high enantioselectivity.

  DOI：

  10.1021/ol0613822
• 作为产物：
  描述：

  甲基(2S)-1-甲酰基吡咯烷-2-羧酸酯 在 四氯化锡 、 N,N,N,N-tetraethylammonium tetrafluoroborate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 methyl trans-N-formyl-α'-(2,4,6-triethylphenyl)-L-prolinate
  参考文献：
  名称：

  New Efficient Organic Activators for Highly Enantioselective Reduction of Aromatic Ketones by Trichlorosilane

  摘要：

  Aryl ketones were reduced to the corresponding alcohols with excellent enantioselectivity (up to 99.7% ee) by Cl3SiH in the presence of a catalytic amount of N-formyl-alpha '-(2,4,6-triethylphenyl)-L-proline as an activator. Both carboxyl group at the alpha-position of the activator and 2,4,6-triethylphenyl group at the alpha '-position were critical for the high enantioselectivity.

  DOI：

  10.1021/ol0613822

文献信息

• Diastereoselective arylation of l-proline derivatives at the 5-position
  作者：Osamu Onomura、Peter G. Kirira、Toshimitsu Tanaka、Shinsuke Tsukada、Yoshihiro Matsumura、Yosuke Demizu

  DOI：10.1016/j.tet.2008.06.004

  日期：2008.8

  Diastereoselective introduction of nucleophiles into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Methoxycarbonylated or benzyloxycarbonylated L-proline derivatives reacted with arene to give cis-arylated products. On the other hand, N-benzoylated L-proline derivative preferentially gave trans-arylated product, which could be easily transformed into optically active C-2-symmetrical pyrrolidine derivative. Such derivative 5 worked well as an organic activator in the asymmetric reduction of aromatic imines by Cl3SiH. (C) 2008 Elsevier Ltd. All rights reserved.