lithium ephedrate | 75844-46-1

• 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 ephedrate
• 英文别名: lithium;(1R,2S)-2-(methylamino)-1-phenylpropan-1-olate
• CAS: 75844-46-1
• 化学式: C₁₀H₁₄NO*Li
• 分子量: 171.168
• InChiKey: ZESVOWDCGWTRLL-GNAZCLTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  麻黄碱 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 lithium ephedrate
  参考文献：
  名称：

  Chelation of 2-substituted 1-lithoxides: structural and energetic factors of relevance to synthetic organic chemistry

  摘要：

  A number of lithium 2-(methylamino)-, 2-(dimethylamino)-, 2-methoxy-, and 2-(isopropylthio)-substituted-1-phenyl-1-propoxides were studied as models for asymmetric synthetic strategies for which lithium chelation between two electronegative atoms has frequently been invoked. The heats of formation of these alkoxides were determined by deprotonating the alcohols with lithium bis(trimethylsilyl)amide in a solution calorimeter. Aggregation numbers for the substituted alcohols and their corresponding lithium alkoxides were obtained with freezing point depression and vapor pressure osmometry in THF, benzene, and dioxane. In several cases, solution structures were obtained through H-1, Li-6, and 2D Li-6-H-1 NOE (HOESY) NMR spectroscopy. Solid-state structures of lithium (+)-N-methylpseudoephedrate and (-)-N-methylephedrate (+)-N-methylpseudoephedrate and (-)-N-methylephedrate (as the benzene solvate) were obtained by X-ray crystallography, and both were found to be present as tetramers in which the dimethylamino nitrogen atoms were coordinated to the lithium cations to form five-membered chelate rings. The lithium alkoxides were either tetramers or hexamers in nonpolar solvents; however, the alkoxides' solution structures were very complex in THF as evidenced by several Li-6 resonances observed in the Li-6 NMR spectra at low temperatures. Intramolecular lithium chelation was found to occur in each alkoxide in dioxane and benzene. The enthalpies of chelational stabilization were estimated by comparing their heats of deprotonation with those of nonchelatable 2-alkyl-substituted analogues. The stabilization enthalpies ranged from 5 to 11 kcal/mol per alkoxide molecule.

  DOI：

  10.1021/ja00016a045
• 作为试剂：
  描述：

  苯甲醛 、 3-溴丙烯 在 chromium dichloride 、 lithium ephedrate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-1-苯基-3-丁烯-1-醇 、 (R)-1-Phenylbut-3-en-1-ol
  参考文献：
  名称：

  Cazes, Bernard; Verniere, Catherine; Gore, Jacques, Synthetic Communications, 1983, vol. 13, # 1, p. 73 - 79

  摘要：

  DOI：