(1S,2S)-(+)-1-chloro-1-phenyl-2-propylamine hydrochloride

• 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: (1S,2S)-(+)-1-chloro-1-phenyl-2-propylamine hydrochloride
• 英文别名: (1S,2S)-chlorodeoxynorpseudoephedrine hydrochloride；(1S,2S)-1-chlor-1-phenyl-2-propylammoniumchlorid；(1S,2S)-1-chloro-1-phenylpropan-2-amine;hydrochloride
• 化学式: C₉H₁₂ClN*ClH
• 分子量: 206.115
• InChiKey: YVZNNEJGVRRITK-DKXTVVGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2S)-(+)-1-chloro-1-phenyl-2-propylamine hydrochloride 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 (-)-(2S,3R)-cis-2-methyl-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：

  去甲麻黄碱 在 五氯化磷 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以75%的产率得到(1S,2S)-(+)-1-chloro-1-phenyl-2-propylamine hydrochloride
  参考文献：
  名称：

  （2 R，3 S）-（-）-2-苯基-3-甲基氮丙啶的合成

  摘要：

  我们报告的氮丙啶的全合成3，在的碳原子的（1个羟基涉及双瓦尔登翻转两步的方法进行[R，2小号） -降麻黄碱，（ - ） - 1，其被用作，起始材料。化合物3首次以固体形式获得，因此可以确定其明确的X射线结构。

  DOI：

  10.1016/s0957-4166(97)00271-1

文献信息

• Synthesis of (2R,3S)-(−)-2-phenyl-3-methylaziridine
  作者：Alberto Galindo、F. Laura Orea、Dino Gnecco、Raúl G. Enríquez、R. Alfredo Toscano、William F. Reynolds

  DOI：10.1016/s0957-4166(97)00271-1

  日期：1997.9

  We report the total synthesis of aziridine 3, carried out in a two-step method involving double Walden inversion at the carbon atom bearing the hydroxy group of (1R,2S)-(−)-norephedrine, 1, which was used as starting material. Compound 3 was obtained for the first time as a solid therefore allowing its unambiguous X-ray structure determination.

  我们报告的氮丙啶的全合成3，在的碳原子的（1个羟基涉及双瓦尔登翻转两步的方法进行[R，2小号） -降麻黄碱，（ - ） - 1，其被用作，起始材料。化合物3首次以固体形式获得，因此可以确定其明确的X射线结构。
• Funktionelle Phosphane
  作者：Lutz Dahlenburg、Rainer Götz

  DOI：10.1016/s0022-328x(00)00520-9

  日期：2001.1

  The preparation of optically active beta -aminophosphane ligands, (-)-(1R,2S)-Ph2PCH(Ph)CH(Me)NH2 (5), (+)-(1S,2S)Ph2PCH(Ph)CH(Me)NH2 (6), (-)-(1R,2R)-Ph2PCH(Ph)CH(Me)NHMe (7), and (1R,2S)-Ph2PCH(Ph)CH(Me)NHSO2Me (8), as well as of related beta -aminophosphinites, (+)-(1R,2S)-Ph2POCH(Ph)CH(Me)NH2 (9), (-)-(1R,2R)-Ph2POCH(Ph)CH(Me)NHMe (10), (+)-(1S,2S)-Ph2POCH(Ph)CH(Me)NHMe (11), and (-)-(1R,2S)-Ph2POCH(Ph)CH(Me)NHMe (12), from commercially available ephedrine, norephedrine, and pseudoephedrine enantiomers is reported. Ligands 6 and 7 react with [M(eta (4)-1,5-C8H12)(2)]BF4 (M = Rh, Ir) to afford the P,N chelate complexes [(1S,2S)-Ph2PCH(Ph)CH(Me)NH2-kappaN,kappaP}Ir(eta (4)-1,5-C8H12)]BF4 (13), [(1R,2R)-Ph2PCH(Ph)CH(Me)NHMe-kappaN,kappaP}Ir(eta (4)-1,5-C8H12)]BF4 (14), and [(1R,2R)-Ph2PCH(Ph)CH(Me)NHMe-kappaN,kappaP}Ir(eta (4)-1,5-C8H12)]BF4 (15), Of which 14 and 15 exist as mixtures of three sterically locked ring conformers. The molecular structures of the prevailing lambda (R-C,R-C,S-N) form of rhodium complex 14, of beta -aminophosphane 8 and of the hydrochloride of ligand 7 were determined by single-crystal X-ray diffraction. In the presence of added triethylamine, iridium complex 15 catalyzes the enantioselective hydrogenation of acetophenone, giving (-)-(S)-1-phenylethanol in modest enantiomeric excess (40%). (C) 2001 Elsevier Science B.V. All rights reserved.
• Synthesis of Chiral cis-1,2,3-Trisubstituted Aziridines
  作者：Tuyen Nguyen Van、Norbert De Kimpe

  DOI：10.1016/s0040-4020(00)00627-x

  日期：2000.9

  Chiral cis-1,2,3-trisubstituted aziridines were conveniently synthesized from (1R,2S)-(-)- or (1S,2R)-(+)-norephedrine via the corresponding chiral N-(arylidene)-beta-chloroamines. The enantiomeric purity of the chiral aziridines (e.e. >98%) was established by NMR spectroscopy utilizing (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.
• KNIEZO L.; KRISTIAN P.; BUDESINSKY M.; HAVRILOVA K., COLLECT. CZECH. CHEM. COMMUN., 1981, 46, NO 3, 717-728
  作者：KNIEZO L.、 KRISTIAN P.、 BUDESINSKY M.、 HAVRILOVA K.

  DOI：——

  日期：——