(S)-N,N-diisopropyl-N^α-(benzyloxycarbonyl)prolinamide | 154780-21-9

• 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: (S)-N,N-diisopropyl-N^α-(benzyloxycarbonyl)prolinamide
• 英文别名: benzyl (2S)-2-[di(propan-2-yl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 154780-21-9
• 化学式: C₁₉H₂₈N₂O₃
• 分子量: 332.443
• InChiKey: VHECNBBYYSNYIJ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N,N-diisopropyl-N^α-(benzyloxycarbonyl)prolinamide 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 生成 (S)-2-(diisopropylaminomethyl)pyrrolidine
  参考文献：
  名称：

  Homochiral Lithium Amides: Enantioselective Deprotonation of Cyclohexene Oxide

  摘要：

  Reaction of cyclohexene oxide with chiral lithium amides has been studied and (S)-2-cyclohexen-l-ol was prepared in 20-82% ee. The optical purity was determined by proton NMR measurement of a-methoxy-a(trifluoromethyl)phenylacetic acid (MTPA) derivative of the corresponding alcohol.

  DOI：

  10.1080/00397919408011196
• 作为产物：
  描述：

  二异丙胺 、 N-苄氧羰基-L-脯氨酸 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 生成 (S)-N,N-diisopropyl-N^α-(benzyloxycarbonyl)prolinamide
  参考文献：
  名称：

  Homochiral Lithium Amides: Enantioselective Deprotonation of Cyclohexene Oxide

  摘要：

  Reaction of cyclohexene oxide with chiral lithium amides has been studied and (S)-2-cyclohexen-l-ol was prepared in 20-82% ee. The optical purity was determined by proton NMR measurement of a-methoxy-a(trifluoromethyl)phenylacetic acid (MTPA) derivative of the corresponding alcohol.

  DOI：

  10.1080/00397919408011196

文献信息

• CATALYTIC ENANTIOSELECTIVE SILYLATIONS OF SUBSTRATES
  申请人：Hoveyda Amir H.

  公开号：US20090312559A1

  公开（公告）日：2009-12-17

  The present invention provides methods, compositions and systems for silylation of substrates, including direct asymmetric silylation of a substrate to provide enantiomerically enriched silylated products.

  本发明提供了用于硅烷化底物的方法、组合物和系统，包括直接不对称硅烷化底物以提供对映选择性富集的硅烷化产物。
• Small organic molecule catalyzed enantioselective direct aldol reaction in water
  作者：Swapandeep Singh Chimni、Dinesh Mahajan

  DOI：10.1016/j.tetasy.2006.07.016

  日期：2006.8

  Protonated pyrrolidine based small organic molecules have been designed and evaluated for the asymmetric direct aldol reaction in water. The designed organocatalysts are multifunctional in nature and exploit the combined effect of hydrogen bonding and hydrophobic interactions for enantioselective catalysis in water. As a result a unique direct asymmetric aldol reaction in water catalyzed by a small organic molecule having an amide linkage has been developed. The developed catalyst affords chiral beta-hydroxyketones in good yields (93%) and enantioselectivities (upto 62%) in water. (c) 2006 Elsevier Ltd. All rights reserved.
• Homochiral Lithium Amides: Enantioselective Deprotonation of Cyclohexene Oxide
  作者：Bhuniya、Singh

  DOI：10.1080/00397919408011196

  日期：1994.2

  Reaction of cyclohexene oxide with chiral lithium amides has been studied and (S)-2-cyclohexen-l-ol was prepared in 20-82% ee. The optical purity was determined by proton NMR measurement of a-methoxy-a(trifluoromethyl)phenylacetic acid (MTPA) derivative of the corresponding alcohol.