(1S,2S)-N-甲基-1-苯基-1-氯-2-丙胺 | 94133-42-3

• 物质功能分类: 生物 - 生化试剂盒
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1S,2S)-N-甲基-1-苯基-1-氯-2-丙胺
• 中文别名: 2-噻吩甲酰胺,N-(3,4-二甲基苯基)-
• 英文名称: (+)-Chloroephedine hydrochloride
• 英文别名: (1S,2S)-(2-chloro-1-methyl-2-phenyl-ethyl)-methylamine hydrochloride；(1S,2S)-chlorodeoxypseudoephedrine hydrochloride；1R,2R-chloro-deoxy-norephedrine hydrochloride；((1S,2S)-2-chloro-1-methyl-2-phenyl-ethyl)-methyl-amine; hydrochloride；((1S,2S)-2-Chlor-1-methyl-2-phenyl-aethyl)-methyl-amin; Hydrochlorid；(S-(R*,R*))-beta-Chloro-N,alpha-dimethylphenethylamine hydrochloride；(1S,2S)-1-chloro-N-methyl-1-phenylpropan-2-amine;hydrochloride
• CAS: 94133-42-3
• 化学式: C₁₀H₁₄ClN*ClH
• 分子量: 220.142
• InChiKey: ICZRAESMLGJTOQ-KXNXZCPBSA-N

物化性质

• 熔点：
  184 - 188°C
• 溶解度：
  DMSO（少许）、甲醇（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 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：
  12
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 储存条件：
  -20°C，密闭保存，干燥条件

制备方法与用途

氯普伪麻黄碱是当使用(+)伪麻黄碱或(-)麻黄碱作为前体物质非法制造(+)甲基苯丙胺时产生的副产品。

反应信息

• 作为反应物：
  描述：

  (1S,2S)-N-甲基-1-苯基-1-氯-2-丙胺 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 1,2-dimethyl-3-phenylaziridine
  参考文献：
  名称：

  Efficient synthesis of cis-thiazolidinethiones derived from ephedrines

  摘要：

  The reaction of chlorodeoxypseudoephedrine or chlorodeoxynorpseudoephedrine hydrochlorides with sodium dithiocarbonate in stirring ethanol at 0 degrees C to stereoselectively afford the corresponding cis-thiazolidinethiones in good yields (81% and 95%) is reported. The in situ formation of a cis-aziridine to explain the presence of trans-thiazolidinethione as a side product is proposed when the same reaction was carried out at room temperature. In addition, a 70:30 mixture of trans-isomers of a thiazolidinethione/isothiazolidinethione was formed when a cis-aziridine NH was reacted with carbon disulfide in refluxing ethanol. The analogous reaction with cis-aziridine N-Me stereoselectively affords the corresponding cis-thiazolidinethione. The H-1 and C-13 NMR data of the thiazolidinethiones were assigned. cis-3,4-Dimethyl-5-phenylthiazolidine-2-thione was crystallized from ethanol and its X-ray diffraction structure was analyzed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.016
• 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 (1S,2S)-N-甲基-1-苯基-1-氯-2-丙胺
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Syntheses of optically active 2-(2-benzothiazolylimino)-heterazolidines
  作者：Alejandro Cruz、Martha Gayosso、Rosalinda Contreras

  DOI：10.1002/hc.1089

  日期：——

  The syntheses of compounds 4R, 5R-2-[2-benzothiazolylimino]-3-hydro-4-methyl-5-phenylthiazolidine (5a), 4S,5S-2-[2-benzothiazolylimino]-3,4-dimethyl-5-phenylthiazolidine (5b), 4R,5S-[2-benzothiazolylimino]-3-hydro-4-methyl-5-phenyloxazolidine (5c), 4R,5S-2-[2-benzothiazolyl-imino]-3,4-dimethyl-5-phenyloxazolidine (5d), and 4R,5S-2-[2-benzothiazolylimino]-1,3,4-trimethyl-5-phenylimidazolidine (5e) are

  化合物4R, 5R-2-[2-benzothiazolylimino]-3-hydro-4-methyl-5-phenylthiazolidine (5a), 4S,5S-2-[2-benzothiazolylimino]-3,4-dimethyl-5的合成-苯基噻唑烷 (5b), 4R,5S-[2-benzothiazolylimino]-3-hydro-4-methyl-5-phenyloxazolidine (5c), 4R,5S-2-[2-benzothiazolyl-imino]-3,4-二甲基报道了 -5-苯基恶唑烷 (5d) 和 4R,5S-2-[2-苯并噻唑亚氨基]-1,3,4-三甲基-5-苯基咪唑烷 (5e)。讨论了反应产物的立体化学和化合物 5a-d 的 X 射线衍射分析。化合物 5a-d 呈现平面结构。我们发现 5a 和 5b 的噻唑烷 S1 原子和苯并噻唑 N9 原子之间的距离很短（分别为
• 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。
• Cobalt(II), nickel(II) and copper(II) compounds derived from template reactions of enantiomerically pure 2-amino-thiazoles
  作者：Raúl Ramírez-Trejo、Angelina Flores-Parra、José Adrián Peña-Hueso、Edgar Mijangos、Rosalinda Contreras、Norah Barba-Behrens

  DOI：10.1016/j.poly.2009.12.003

  日期：2010.2

  Abstract Herein we report the syntheses and structural analyses of three coordination compounds Co(L)2 (3), Ni(L)2, (4) and Cu(L)2 (5) (L = bis[(4R,5R)-4-methyl-5-phenyl-4,5-dihydro-thiazol-2-yl]-amine) prepared by template reactions from the optically active ligand (4R,5R)-4-methyl-5-phenyl-4,5-dihydro-thiazol-2-yl-amine (1) and CoCl2·6H2O, NiBr2·3H2O or Cu(OAc)2·H2O The template reactions involve

  摘要本文报道了三种配位化合物Co（L）2（3），Ni（L）2，（4）和Cu（L）2（5）（L = bis [（4R，5R）通过旋光性配体（4R，5R）-4-甲基-5-苯基-4,5通过模板反应制备的-4-甲基-5-苯基-4,5-二氢噻唑-2-基]-胺） -二氢噻唑-2-基-胺（1）和CoCl2·6H2O，NiBr2·3H2O或Cu（OAc）2·H2O模板反应涉及两个分子的噻唑-2-基-胺的缩合和一个分子的消除NH3。生成的二齿配体通过亚胺氮原子与金属离子配位，形成一个六元环，呈现出电子离域化，平均四个M–N键长。金属原子扭曲的四面体几何结构为化合物3-5的复杂电子光谱提供了空间。由三个阳离子（4S，由（4S，5S）-3,4-二甲基-5反应制得的5S）-3,4-二甲基-5-苯基-噻唑烷-2-吡咯铵，三价双（硫氰基）溴化钴和一溴化二阴离子还描述了-苯基-噻唑烷-2-亚硫氰酸铵（2）和CoBr 2
• 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.