(5S,6R)-4,5-dimethyl-6-phenyl-2-morpholone | 130753-28-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5S,6R)-4,5-dimethyl-6-phenyl-2-morpholone
• 英文别名: (5s,6r)-4,5-Dimethyl-6-phenylmorpholin-2-one
• CAS: 130753-28-5
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: IEWLSENRWXRYLB-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,6R)-4,5-dimethyl-6-phenyl-2-morpholone 在 一水合肼 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 2.5h， 生成 acetylacetone N-l-ephedrinylacetylhydrazone
  参考文献：
  名称：

  Nurkenov; Kulakov; Gazaliev, Russian Journal of General Chemistry, 1999, vol. 69, # 1, p. 1669 - 1672

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,2S)-2-<(β-hydroxy-α-methylphenethyl)methylamino>-N,N-dimethylacetamide 在 sodium carbonate 作用下， 以 xylene 为溶剂， 反应 24.0h， 以88%的产率得到(5S,6R)-4,5-dimethyl-6-phenyl-2-morpholone
  参考文献：
  名称：

  Stereo- and regioselective synthesis of chiral diamines and triamines from pseudoephedrine and ephedrine

  摘要：

  N-Alkylated derivatives of (1R,2R)-(-)-pseudoephedrine and (1R,2S)-(-)-ephedrine afford, upon reaction with methanesulfonyl chloride, mixtures of 1-chloro- and 2-chloroamines which undergo stereospecific and regiospecific substitution reactions with sodium azide, amines, imides, thiols, thiolacetic acid, N-hydroxyphthalimide, and diphenylphosphine to give, in each case, a single isomeric product. These substitution reactions proceed with net retention of configuration. The procedure is not readily extended to nonbenzylic systems which give widely varying yields and regioisomeric ratios. The methodology provides for a facile synthesis of chiral diamines, triamines, aminohydroxylamines, aminothiols, aminosulfides, and aminophosphines from chiral 1,2-amino alcohols wherein either the amine or alcohol functionality is benzylic.

  DOI：

  10.1021/jo00032a013

文献信息

• Fused heterocycles derived from pseudoephedrine and ephedrine
  作者：Norberto Farfán、Rosa L. Santillan、Dolores Castillo、Reyna Cruz、Pedro Joseph-Nathan、Jean-Claude Daran

  DOI：10.1139/v92-351

  日期：1992.11.1

  2R)-(−)-pseudoephedrine or (1R, 2S)-(−)-ephedrine with glyoxal is reported. In the case of pseudoephedrine, the nuclear magnetic resonance data of the crude reaction mixture indicate the presence of three isomeric compounds (5, 6, and 7), which were separated by fractional crystallization, while ephedrine afforded the oxazino-oxazine 8 and the known (5S*,6R*)-4,5-dimethyl-6-phenyl-1,4-oxazin-2-one

  据报道，通过 (1R, 2R)-(-)-伪麻黄碱或 (1R, 2S)-(-)-麻黄碱与乙二醛缩合形成杂双环。在伪麻黄碱的情况下，粗反应混合物的核磁共振数据表明存在三种异构化合物（5、6 和 7），它们通过分级结晶分离，而麻黄碱提供恶嗪并恶嗪 8 和已知的(5S*,6R*)-4,5-二甲基-6-苯基-1,4-恶嗪-2-one (9)。具有 cis-[1,4]oxazino[3,2-b]-1,4-oxazine (5 and 8) 和 2,2'-bioxazolidine 型结构 (6) 的新化合物结构的决定性光谱证据和 7) 通过测量 13C 卫星耦合常数在 300 MHz 1H nmr 光谱中获得，并结合使用改进的 Karplus 类型关系评估二面角。所有新化合物的明确 1H 和 13C nmr 光谱归属是使用二维碳 - 质子相关实验完成的。已知的 5a,6,11a,12-四氢...
• Nurkenov; Gazaliev; Kanakhin, Russian Journal of General Chemistry, 1998, vol. 68, # 8, p. 1259 - 1260
  作者：Nurkenov、Gazaliev、Kanakhin、Kulakov、Zhurinov

  DOI：——

  日期：——
• Nurkenov; Gazaliev; Kanakhin, Russian Journal of General Chemistry, 1997, vol. 67, # 7, p. 1152 - 1152
  作者：Nurkenov、Gazaliev、Kanakhin、Kulakov、Zhurinov

  DOI：——

  日期：——
• Synthesis and crystalline and molecular structures of the morpholinylamide of N(R)-l-ephedrinylacetic acid
  作者：K. M. Turdybekov、A. B. Shalbaeva、O. A. Nurkenov、A. V. Kanakhin、I. V. Kulakov、A. M. Gazaliev

  DOI：10.1007/bf02238218

  日期：1999.1

  The synthesis of the morpholinylamide of N(R)-1-ephedrinylacetic acid has been achieved by the interaction of (5S,6R)-4,5-dimethyl-6-phenylmorpholin-2-one with morpholine, and its structure has been shown by IR and PMR spectroscopies and x-ray structural analysis.
• DIETER, R. KARL;LAGU, BHARAT;DIETER, JANICE W.;DEO, NIRANJAN;PENNINGTON, +, SYNLETT.,(1990) N, C. 109-110
  作者：DIETER, R. KARL、LAGU, BHARAT、DIETER, JANICE W.、DEO, NIRANJAN、PENNINGTON, +

  DOI：——

  日期：——