N-<1-(2-Pyridyl)ethyl>-(S)-1-phenylethylamine | 192223-36-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-<1-(2-Pyridyl)ethyl>-(S)-1-phenylethylamine
• 英文别名: (S)-α-Methyl-N-(1-phenylethyl)-2-pyridinylmethanamin；(S)-α-methyl-N-(1-phenylethyl)-2-pyridinylmethylamine；(1S)-1-phenyl-N-(1-pyridin-2-ylethyl)ethanamine
• CAS: 192223-36-2
• 化学式: C₁₅H₁₈N₂
• 分子量: 226.321
• InChiKey: FLHJEJWJIZRYOL-UEWDXFNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium 、 N-<1-(2-Pyridyl)ethyl>-(S)-1-phenylethylamine 以 甲醇 为溶剂， 以85-90的产率得到(eta.4-1,5-cycloocatadiene)[(S)-.-alpha.-methyl-N-(1-phenylethyl)-2-pyridinemethanamine-N,N']rhodium hexafluorophosphate
  参考文献：
  名称：

  Brunner, Henri; Reiter, Barbara; Riepl, Georg, Chemische Berichte, 1984, vol. 117, # 4, p. 1330 - 1354

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-α-Methyl-N-<1-(2-pyridinyl)ethyliden>phenylmethanamin 在 lithium diethylaminoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以51%的产率得到N-<1-(2-Pyridyl)ethyl>-(S)-1-phenylethylamine
  参考文献：
  名称：

  氨基硼氢化物。6.使用二乙基氨基硼氢化锂和二异丙基氨基硼氢化锂非对映选择性还原手性亚胺中的碳氮双键

  摘要：

  通过n-BuLi与胺-硼烷反应获得的氨基硼氢化锂（LAB）可以将亚胺轻松还原为相应的仲胺。二乙基氨基硼氢化锂[Li（Et）2 NBH 2 ]和二异丙基氨基硼氢化锂[Li（i-Pr）2 NBH 3 ]还原衍生自α-甲基苄胺的手性脂族和芳族亚胺，得到相应的对映异构体富集的仲胺。从该方法得到的仲胺的产率为非常好的至基本上定量的范围。Li（Et）2 NBH 3和Li（i-Pr）2 NBH 3还原碳氮双键的非对映异构体诱导 从中等到非常好。

  DOI：

  10.1016/s0040-4039(00)73507-6

文献信息

• Addition of Organozincate Reagents to Imines Derived from (S)-1-Phenylethylamine and Ethyl (S)-Valinate—Synthesis of (S)-1-(2-Pyridyl)Alkylamines
  作者：Giuseppe Alvaro、Paolo Pacioni、Diego Savoia

  DOI：10.1002/chem.19970030512

  日期：1997.5

  AbstractTriorganozincates were added to aliphatic aldimines derived from (S)‐1‐phenylethylamine and (S‐valine esters in the presence of boron trifluoride to give secondary amines with low diastereoselectivies. From mixed zincates, most alkyl groups (methyl, ethyl, 1‐heptynyl, but not tert‐butyl) could be transferred. No addition to benzaldimines was observed, but the imines prepared from 2‐pyridinecarboxaldehyde did not require activation by BF3 and underwent selective group transfer from mixed zincates at — 78°C. Excellent diastereoselectivities were observed in the reactions of the 2‐pyridine imine derived from ethyl (S)‐valinate with mixed zincates, in which the methyl group was used as nontransferable ligand, allowing the transfer of alkyl and vinyl groups with excellent to complete selectivity. However, dimethyl(aryl)‐ and dimethyl‐(1‐heptynyl)zincates did not react. (S)‐1‐(2‐Pyridyl)alkylamines were prepared with high optical purity by subsequent removal of the chiral auxiliary.