(1S,1'R)-N-(2'-methoxy-1'-phenylethyl)-1-phenylethylamine | 90933-77-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,1'R)-N-(2'-methoxy-1'-phenylethyl)-1-phenylethylamine
• 英文别名: <2-Methoxy-(R)-1-phenylethyl><(S)-1-phenylethyl>amine；(R)-N-<2-methoxy-1-phenylethyl>-(S)-α-methylbenzylamine；(1R)-2-methoxy-1-phenyl-N-[(1S)-1-phenylethyl]ethanamine
• CAS: 90933-77-0
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: GHPCMNNQDTWKIX-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,1'R)-N-(2'-methoxy-1'-phenylethyl)-1-phenylethylamine 在 正丁基锂 作用下， 生成 lithium (2-methoxy-(R)-1-phenylethyl)((S)-1-phenylethyl)amine
  参考文献：
  名称：

  Enantioselective addition of n-butyllithium to benzaldehyde in the presence of chiral lithium amides

  摘要：

  DOI：

  10.1016/s0040-4039(01)81559-8
• 作为产物：
  描述：

  [2-Methoxy-1-phenyl-eth-(Z)-ylidene]-((S)-1-phenyl-ethyl)-amine 生成 (1S,1'R)-N-(2'-methoxy-1'-phenylethyl)-1-phenylethylamine
  参考文献：
  名称：

  ELEVELD, M. B.;HOGEVEEN, H., TETRAHEDRON LETT., 1984, 25, N 45, 5187-5190

  摘要：

  DOI：

文献信息

• Diastereoselective Addition of Chiral Aliphatic Imines and 2-Alkyl-1,3-oxazolidines to Organometallic Reagents.
  作者：Kimio HIGASHIYAMA、Hideki FUJIKURA、Hiroshi TAKAHASHI

  DOI：10.1248/cpb.43.722

  日期：——

  The reaction of organocerium reagents with chiral aliphatic imines derived from (R)-O-methylphenylglycinol afforded the corresponding amines with high diastereoselectivity. In contrast, the reaction of Grignard reagents with chiral 2-alkyl-1, 3-oxazolidines derived from (R)-N-methylphenylglycinol afforded the amines with changeover in diastereoselectivity.

  有机铈试剂与源自(R)-O-甲基苯基甘氨醇的手性脂肪胺反应，得到相应的胺，具有高的非对映选择性。相反，格氏试剂与源自(R)-N-甲基苯基甘氨醇的手性2-烷基-1,3-噁唑烷反应时，胺的非对映选择性发生了变化。
• Reversal of Diastereofacial Selectivity in the Addition Reaction of Organometallics to Chiral Imines
  作者：Yutaka Ukaji、Toshiyuki Watai、Takashi Sumi、Tamotsu Fujisawa

  DOI：10.1246/cl.1991.1555

  日期：1991.9

  It was observed that diastereofacial selectivity in the addition reaction of organometallics to the chiral imines derived from (R)-2-methoxy-1-phenylethylamine was regulated under appropriate conditions; i. e., organolithium and organocerium reagents added from the re-face of the chiral imines selectively, while organocopper reagents attacked from the si-face. The utility of the present method was

  观察到有机金属化合物与衍生自 (R)-2-甲氧基-1-苯乙胺的手性亚胺的加成反应中的非对映选择性在适当条件下得到调节；即，有机锂和有机铈试剂从手性亚胺的表面选择性地添加，而有机铜试剂从硅表面攻击。本方法的效用在 solenopsin A 的对映选择性合成中得到了证明。
• Diastereoselective synthesis of chiral secondary amines with two chiral centers directly attached to the nitrogen atom
  作者：M. B. Eleveld、H. Hogeveen、E. P. Schudde

  DOI：10.1021/jo00369a016

  日期：1986.9
• Enantioselective reduction of acetophenone by borane.chiral amine complexes
  作者：M.B. Eleveld、H. Hogeveen

  DOI：10.1016/s0040-4039(00)84060-5

  日期：1986.1
• A Multinuclear NMR Study of a Chiral Lithium Amide with an Intramolecular Chelating Methoxy Group in Coordinating Solvents at the Slow Ligand Exchange Limit
  作者：Goeran Hilmersson、Oejvind Davidsson

  DOI：10.1021/jo00128a045

  日期：1995.11

  The dynamics and solution structure of the lithium salt of 2-methoxy-[(R)-1-phenylethyl][(S)-1-phenylethyl]amine (1) in diethyl ether (DEE), tetrahydrofuran (THF), dimethoxyethane (DME), N,N,N',N'-tetramethylethylene diamine (TMEDA) and toluene were studied by multinuclear NMR spectroscopy at temperatures down to -100 degrees C. The lithium salt of 1 (3) is a dimer with C-2 symmetry in DEE with two different lithium resonances in the Li-6 NMR. The activation parameters for the intra-aggregate lithium exchange in DEE has been determined by line-shape analysis, Delta H double dagger = 50 +/- 2 kJ/mol; Delta S double dagger = -10 +/- 10 J/(mol K). The observed low activation entropy and the concentration-independent coalescence temperature, T-c = 250 K, suggest an intra-aggregate lithium exchange without assistance by additional ligands in the rate-limiting transition state. Slow ligand exchange on the NMR time scale for 3 in DEE, THF, DME, and TMEDA were observed by both C-13 and Li-6 NMR spectroscopy. It was established that 3 coordinates only one solvent ligand indicating that one of the lithiums in 3 is tetracoordinate (two nitrogens and two methoxy groups) and the other is tricoordinate (two nitrogens and one solvent ligand). A slightly broader Li-6 signal and a much broader Li-7 signal were observed for the tricoordinate lithium compared to the tetracoordinate one. This effect is probably due to the less symmetric local environment around the tricoordinate lithium. THF titration of 3 in DEE showed that THF has substantially greater affinity for 3 than does DEE. The addition of 0.5 equivalents of THF to a DEE solution of 3 afforded THF solvated 3. At higher concentrations of THF, monomers of the lithium salt of 1 were observed, and in neat THF only monomers were observed. From a temperature study at low THF concentrations, the enthalpy and entropy for the dimer-monomer equilibrium were determined, Delta(r) degrees = -33 +/- 1 kJ/mol; Delta(r)S degrees = -185 +/- 4 J/(mol K). The Li-6,H-1-HOESY spectra of 3 ligated by different ethers showed similar dimer structures. Titration of 3 in toluene with DME showed the presence of DME solvated monomers and dimers of 3 with DME probably functioning as a monodentate ligand. Titration of 3 in toluene with TMEDA resulted in the formation of mostly monomers with bidentate TMEDA ligation. Slow ligand exchange was only observed for monosolvated and tricoordinate lithium cations.