(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

• Rhodium complex with unsymmetrical vicinal diamine ligand: excellent catalyst for asymmetric transfer hydrogenation of ketones
  作者：Sudhindra H. Deshpande、Vaishali S. Shende、Savita K. Shingote、Debamitra Chakravarty、Vedavati G. Puranik、Raghunath V. Chaudhari、Ashutosh A. Kelkar

  DOI：10.1039/c5ra08220j

  日期：——

  investigated. The reaction mixture is homogeneous in methanol unlike in water, where substrate and product are insoluble in water and form separate phase, sodium formate being soluble in water. The activity and enantioselectivity obtained for ATH of ketones using [Rh(Cp*)Cl2]2 and unsymmetrical vicinal diamine ligand as catalyst was comparable with the C2 symmetric benchmark ligands like TsDPEN ((1R,2R)-N-(p-tolylsulfonyl)-1

  从便宜的起始原料如去氧麻黄碱合成了新的不对称邻位二胺配体，其胺和磺酰胺基团的区域和立体位置发生系统性变化。已经研究了使用过渡金属配合物和以甲酸钠为氢源的单甲苯磺酸化不对称邻位二胺配体的新衍生物在水中和甲醇中对芳族烷基酮的催化不对称转移加氢（ATH）。以优异的对映选择性（> 95％ee）和[Rh（CP *）Cl 2 ] 2和配体4转化酮（> 95％）获得手性仲醇作为催化剂。与使用水作为溶剂相比，发现使用甲醇作为酮（以甲酸钠为氢源）进行ATH的溶剂时，对映选择性略高，并且发现与所有研究的酮均相符。与在水中不同，反应混合物在甲醇中是均相的，在水中，底物和产物不溶于水并形成分离的相，而甲酸钠则溶于水。的活性和对映选择性使用酮为ATH获得的[Rh（CP *）氯2 ] 2和不对称连位二胺配体作为催化剂是与可比较的C ^ 2点对称基准的配体等TsDPEN（（1 - [R，2 - [R ） - ñ - （p-甲苯基磺酰基）-1
• 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：——