lithium (2-methoxy-(R)-1-phenylethyl)((S)-1-phenylethyl)amine | 95447-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: lithium (2-methoxy-(R)-1-phenylethyl)((S)-1-phenylethyl)amine
• 英文别名: N-Lithium (R)-N-2-methoxy-1-phenyl-(S)-α-methylbenzylamine；[2-methoxy-(R)-1-phenylethyl][2-lithium-(S)-1-phenylethyl] amide；lithium;[(1R)-2-methoxy-1-phenylethyl]-[(1S)-1-phenylethyl]azanide
• CAS: 95447-92-0
• 化学式: C₁₇H₂₀NO*Li
• 分子量: 261.293
• InChiKey: LKWIMJXULOYMAW-RVXRQPKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  20
• 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：
  10.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  正丁基锂 、 lithium (2-methoxy-(R)-1-phenylethyl)((S)-1-phenylethyl)amine 以 乙醚 为溶剂， 生成 、 丁烷
  参考文献：
  名称：

  On the Mechanism of Internal ortho-Lithiation in a Mixed Complex Between BuLi and a Chiral Lithium Amide

  摘要：

  The chiral lithium amide Li-1, prepared from (S)-N-[(R)-2-methoxy-1-phenylethyl]-alpha-methylbenzylamine 1, is known to form a mixed complex with BuLi, i.e., Li-1/BuLi. When this complex is kept at room temperature for 3 - 5 h, a regioselective lithiation of one of the ortho-C-atoms in the amide occurs. Kinetic studies indicate that this reaction proceeds within the mixed aggregate with a first-order rate constant for the rate-limiting step k(2) = 9.4 x 10(-4) s(-1) (DeltaG(273K)(not equal) = 21 kcal mol(-1)). Molecular modeling (semi-empirical PM3) suggests that the observed selectivity and reactivity are a consequence of the solvation and structure of the mixed complex, i. e., an example of a complex induced proximity effect (CIPE).

  DOI：

  10.1002/1522-2675(200211)85:11<3814::aid-hlca3814>3.0.co;2-o
• 作为产物：
  描述：

  2-甲氧基苯乙酮 在 正丁基锂 、 氢气 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

文献信息

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

  DOI：——

  日期：——