chlorodeoxypseudoephedrine hydrochloride | 101859-99-8

• 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: chlorodeoxypseudoephedrine hydrochloride
• 英文别名: ((1R,2R)-2-chloro-1-methyl-2-phenyl-ethyl)-methyl-amine; hydrochloride；((1R,2R)-2-Chlor-1-methyl-2-phenyl-aethyl)-methyl-amin; Hydrochlorid
• CAS: 101859-99-8
• 化学式: C₁₀H₁₄ClN*ClH
• 分子量: 220.142
• InChiKey: ICZRAESMLGJTOQ-SCYNACPDSA-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：

  chlorodeoxypseudoephedrine hydrochloride 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 16.25h， 生成 2-Imino-3,4-dimethyl-5-phenyl-oxazolidin
  参考文献：
  名称：

  Reactivity of chlorodeoxypseudoephedrines with oxo-, thio-, and selenocyanates

  摘要：

  Herein, the reactivity of chlorodeoxypseudoephedrine hydrochlorides with oxo-, thio-, and selenocyanate nucleophiles is reported. 1,3-Heterazolidine-2-iminium or ammonium salts were obtained stereo selectively in most cases. The hard-soft nature of the calcogen atom determines the mechanistic pathway via an S(N)2 (X = O), aziridine intermediate (X = Se), or both (X = S). A simple method to synthesize stereoselectively the trans-isomer of 3,4-dimethyl-5-phenyl-oxazolidine-2-iminium chloride and the cis-isomer of 4-methyl-5-phenyl-oxazoline-2-ammonium chloride, was also found. In addition, heterazolidine-2-imines or amines were liberated from the corresponding salts [Cl- or XCN- (X = O, S, Se)] with aqueous NaOH. Finally, cis-3,4-dimethyl-5-phenyl-oxazolidine-2-iminium chloride, cis-4-methyl-5-phenyl-oxazoline-2-amine, and trans-4-methyl-5-phenyl-selenazoline-2-amine compounds were studied by X-ray diffraction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.012
• 作为产物：
  描述：

  左旋盐酸伪麻黄碱 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 chlorodeoxypseudoephedrine hydrochloride 、 1-Chloro-N-methyl-1-phenylpropan-2-amine hydrochloride
  参考文献：
  名称：

  液相色谱法测定由麻黄碱和伪麻黄碱制得的甲基苯丙胺对映体组成。

  摘要：

  DOI：

  10.1021/ac00121a011

文献信息

• Synthesis of 1,2-aminoazides. Conversion to unsymmetrical vicinal diamines by catalytic hydrogenation or reductive alkylation with dichloroboranes.
  作者：Ariza Benalil、Bertrand Carboni、Michel Vaultier

  DOI：10.1016/s0040-4020(01)91013-0

  日期：1991.9

  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.
• Thiazaborolidines and BH3 adducts derived from thioephedrines
  作者：Alejandro Cruz、Angelina Flores-Parra、Hugo Tlahuext、Rosalinda Contreras

  DOI：10.1016/0957-4166(95)00252-k

  日期：1995.8

  The synthesis of 1,3,2-thiazaborolidine and 2,3-dihydro-2, 1,3-borathiazolidines from reaction of ephedrine disulfide and 3,4-dimethyl-5-phenyl-1,3-thiazolidine-2-thione with BH3-THF is reported. The two reactions afforded optically active borohydride heterocycles. The X-ray diffraction structure of (1R,2R)-(-)-chlorodeoxy-pselrdo-ephedrine hydrochloride, (1R,2R)-(-)-thiosulfonic deoxy-pseudo-ephedrine and (3S,4R,5R)-(+)-2,3-dihydro-3,4-dimethyl-5-phenyl-2, 1,3-borathiazolidine are reported.
• Tanaka, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1950, vol. 70, p. 212,215
  作者：Tanaka

  DOI：——

  日期：——
• Über Umlagerungsreaktionen in der Reihe der Arylpropanolamine
  作者：H. Pfanz、H. Wieduwilt

  DOI：10.1002/ardp.19552881114

  日期：——
• A stereochemical study of optically active thiazolidines
  作者：Alejandro Cruz、Aurora Vásquez-Badillo、Iris Ramos-Garcı́a、Rosalinda Contreras

  DOI：10.1016/s0957-4166(01)00117-3

  日期：2001.4

  We report a stereochemical study of a series of free N-H and N-methylated 1,3-thiazolidines heating H or CH, at C-(2). These compounds were readily prepared from ephedrine and pseudoephedrines. The stereochemistry of the compounds under study was deduced using H-1 and C-13 NMR spectroscopy. Two isomers were found for compounds having a methyl group at C-(2) (i.e. C-(2)HCH3): interconversion of these isomers, presumably via a non-cyclic zwitterionic intermediate, was observed. (C) 2001 Elsevier Science Ltd. All rights reserved.