(S)-N-(1'-phenylethyl)pyrrolidine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-N-(1'-phenylethyl)pyrrolidine
• 英文别名: (S)-1-pyrrolidinyl-1-phenylethane；(S)-1-(1-phenylethyl)pyrrolidine；(S)-1-(1-pyrrolidinyl)-1-phenylethane；1-[(1S)-1-phenylethyl]pyrrolidine
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: UWBGXRMEQVITBS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-N-(1'-phenylethyl)-2-pyrrolidinone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以84%的产率得到(S)-N-(1'-phenylethyl)pyrrolidine
  参考文献：
  名称：

  Sugiyama, Shigeo; Morishita, Kenji; Chiba, Mariko, Heterocycles, 2002, vol. 57, # 4, p. 637 - 648

  摘要：

  DOI：

文献信息

• Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines
  作者：Sophie H. Gilbert、Sergey Tin、José A. Fuentes、Tamara Fanjul、Matthew L. Clarke

  DOI：10.1016/j.tet.2020.131863

  日期：2021.1

  An asymmetric hydrogenation of enamines is efficiently catalysed by rhodium complexed with a fluorinated version of the planar chiral paracyclophane-diphosphine ligand, Phanephos. This catalyst was shown to be very active, with examples operating at just 0.1 mol% of catalyst. This catalyst was then successfully adapted to Direct Asymmetric Reductive Amination, leading to the formation of several tertiary

  铑与平面手性对环烷二膦配体Phanephos的氟化形式络合，有效地催化了烯胺的不对称氢化。该催化剂显示出非常高的活性，实施例仅在催化剂的0.1mol％下操作。然后，如果使用活化的酮/胺配偶体，则该催化剂成功地适应于直接不对称还原胺化反应，导致形成几种具有中等ee的叔胺。
• Secondary amines as coupling partners in direct catalytic asymmetric reductive amination
  作者：Zitong Wu、Shaozhi Du、Guorui Gao、Wenkun Yang、Xiongyu Yang、Haizhou Huang、Mingxin Chang

  DOI：10.1039/c9sc00323a

  日期：——

  The secondary amine participating asymmetric reductive amination remains an unsolved problem in organic synthesis. Here we show for the first time that secondary amines are capable of effectively serving as N-sources in direct asymmetric reductive amination to afford corresponding tertiary chiral amines with the help of a selected additive set under mild conditions (0–25 °C). The applied chiral phosphoramidite

  仲胺参与不对称还原胺化仍然是有机合成中未解决的问题。在这里，我们首次证明仲胺能够有效地作为直接不对称还原胺化中的氮源，在温和条件（0-25°C）下借助选定的添加剂组提供相应的手性叔胺。所应用的手性亚磷酰胺配体很容易由 BINOL 制备并易于修饰。与常见的手性叔胺合成方法相比，该过程更加简洁和可扩展，卡巴拉汀和N-甲基-1-苯乙胺的轻松合成就是例证。
• Asymmetric Hydrogenation of Unfunctionalized Enamines Catalyzed by Iridium Complexes of Chiral Spiro N,N-Diarylphosphoramidites
  作者：Pucha Yan、Jianhua Xie、Qilin Zhou

  DOI：10.1002/cjoc.201090293

  日期：2010.9

  Chiral spiro N,N‐diarylphosphoramidites were synthesized. These new chiral spiro monophosphoramidites were efficient ligands for iridium‐catalyzed asymmetric hydrogenation of unfunctionalized enamines derived from simple alkyl aryl ketones, providing chiral tertiary amines in good enantioselectivities (up to 90% ee).

  合成了手性螺，N，N-二芳基亚磷酰胺。这些新的手性螺单磷酰胺盐是有效的配体，用于铱催化衍生自简单烷基芳基酮的未官能化烯胺的不对称加氢，从而提供了具有良好对映选择性（高达90％ee）的手性叔胺。
• Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Enamines
  作者：Alejandro Baeza、Andreas Pfaltz

  DOI：10.1002/chem.200802576

  日期：2009.2.23

  Optically active tertiary amines are readily prepared by iridium‐catalyzed asymmetric hydrogenation of unfunctionalized enamines (see scheme). The best enantioselectivities with >90 % ee were obtained with N‐aryl‐ and N‐benzyl‐substituted enamines with a terminal double bond. The hydrogenation of enamines derived from cyclic ketones, which has not been reported yet with other catalysts, gave enantiomeric

  旋光性叔胺很容易通过未官能化烯胺的铱催化不对称氢化来制备（参见方案）。具有> 90％的对映选择性最好 ee值与获得的N-芳基-和N-具有末端双键的苄基取代的烯胺。来自环酮的烯胺的氢化（尚未用其他催化剂报道）使对映体过量高达87％。
• Access to chiral tertiary amines via the iridium-catalyzed asymmetric hydrogenation of enamines
  作者：Pradeep Cheruku、Tamara L. Church、Anna Trifonova、Thomas Wartmann、Pher G. Andersson

  DOI：10.1016/j.tetlet.2008.10.035

  日期：2008.12

  The asymmetric hydrogenation of N,N-dialkyl and N-alkyl-N-aryl enamines to chiral tertiary amines was studied. All the N,P-ligated iridium complexes investigated were active catalysts for the reaction, but only those with bicycle-supported oxazoline-phosphine ligands gave reasonable stereoinduction. The best catalyst produced a range of chiral tertiary amines in up to 87% ee.

  研究了N，N-二烷基和N-烷基-N-芳基烯胺不对称氢化为手性叔胺。研究的所有N，P连接的铱络合物都是该反应的活性催化剂，但是只有那些带有自行车支撑的恶唑啉-膦配体的化合物才能产生合理的立体诱导。最好的催化剂可以产生高达87％ee的一系列手性叔胺。