erythro-(1S,2R)-1-chloro-1-phenyl-2-(methylamino)propane hydrochloride | 27270-80-0

• 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: erythro-(1S,2R)-1-chloro-1-phenyl-2-(methylamino)propane hydrochloride
• 英文别名: (-)-Chloroephedine hydrochloride；((1S,2R)-2-chloro-1-methyl-2-phenyl-ethyl)-methyl-amine; hydrochloride；((1S,2R)-2-Chlor-1-methyl-2-phenyl-aethyl)-methyl-amin; Hydrochlorid；(2-Chlor-1-methyl-2-phenyl-aethyl)-methyl-amin; Hydrochlorid
• CAS: 27270-80-0
• 化学式: C₁₀H₁₄ClN*ClH
• 分子量: 220.142
• InChiKey: ICZRAESMLGJTOQ-GNAZCLTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  erythro-(1S,2R)-1-chloro-1-phenyl-2-(methylamino)propane hydrochloride 在 氢氧化钾 、 sodium azide 作用下， 生成 (1R,2S)-1-azido-1-phenyl-2-(N-methylamino)propane
  参考文献：
  名称：

  Synthesis of 1,2-aminoazides. Conversion to unsymmetrical vicinal diamines by catalytic hydrogenation or reductive alkylation with dichloroboranes.

  摘要：

  1,2-aminoazides are easily prepared from 1,2-amino alcohols. Catalytic hydrogenation in the presence of palladium on charcoal or reductive alkylation with dichloroboranes afford with good yields unsymmetrically substituted vicinal diamines.

  DOI：

  10.1016/s0040-4020(01)91013-0
• 作为产物：
  描述：

  (1S,2S)-2-甲氨基-1-苯基丙-1-醇 在 盐酸 作用下， 生成 erythro-(1S,2R)-1-chloro-1-phenyl-2-(methylamino)propane hydrochloride
  参考文献：
  名称：

  Emde, Helvetica Chimica Acta, 1929, vol. 12, p. 393

  摘要：

  DOI：

文献信息

• Chlorination reactions of ephedrines revisited. Stereochemistry and functional groups effect on the reaction mechanisms
  作者：Angelina Flores-Parra、Patricia Suárez-Moreno、Sonia A Sánchez-Ruı́z、Margarita Tlahuextl、Javier Jaen-Gaspar、Hugo Tlahuext、Raúl Salas-Coronado、Alejandro Cruz、Heinrich Nöth、Rosalinda Contreras

  DOI：10.1016/s0957-4166(98)00155-4

  日期：1998.5

  The stereochemistry of the chlorination reactions with SOCl2 of free ephedrine and pseudoephedrine and their hydrochlorides, oxamides and sulfonamides was analyzed. Chlorination of free and hydrochloride erythro isomers occurs with 100% inversion of configuration at C-1 (SN2 mechanism). Chlorination of oxamides and sulfonamides of erythro isomers occurs with retention of the configuration at C-1, (SNi

  分析了游离麻黄碱和伪麻黄碱与SOCl 2氯化反应的立体化学及其盐酸盐，草酰胺和磺酰胺。的自由和盐酸赤式异构体的氯化与C-1（S构型的100％反转发生Ñ 2机构）。赤型异构体的草酰胺和磺酰胺发生氯化反应，保留C-1构型（S N i机理）。所有苏式异构体及其衍生物的盐酸盐，草酰胺或磺酰胺中的氯化反应均得到相同比例的赤型（40％）和苏型（60％）（S N1机制）。用HCl处理DMSO中的盐酸氯脱氧麻黄碱和氯脱氧伪麻黄碱的异构体混合物会改变异构体比例，增加赤型异构体含量（65％）。如果该化合物事先被甲苯磺酸化或转化为酰胺，或者如果该化合物直接被SOCl 2氯化，则使用赤型乙醇胺可以有选择地到达赤型氯胺。
• Liquid chromatographic determination of the enantiomeric composition of methamphetamine prepared from ephedrine and pseudoephedrine
  作者：F. Taylor. Noggle、Jack. DeRuiter、C. Randall. Clark

  DOI：10.1021/ac00121a011

  日期：1986.7.1
• An efficient synthesis of aziridines from ephedrines
  作者：Alejandro Cruz、Itzia Irene Padilla-Martínez、Efrén V. García-Báez

  DOI：10.1016/j.tetasy.2010.05.007

  日期：2010.4

  The reaction of chlorodeoxyephedrine hydrochlorides with one, two, and three molar equivalents of base was studied. Isochlorodeoxypseudoepherines were identified and assigned by H-1 and C-13 NMR data as intermediate compounds in the formation of cis-aziridines. Erythro and threo ephedrinethylethers were isolated as new compounds and analyzed by spectroscopic data. In addition, the erythro isomer was studied by X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved.
• Klosa,J., Journal fur praktische Chemie (Leipzig 1954), 1966, vol. 34, p. 335 - 340
  作者：Klosa,J.

  DOI：——

  日期：——