(5R,6S)-6-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-3,5-diphenyl-5,6-dihydro-4H-1,2-oxazine | 491838-93-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5R,6S)-6-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-3,5-diphenyl-5,6-dihydro-4H-1,2-oxazine
• 英文别名: (5R,6S)-6-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-3,5-diphenyl-5,6-dihydro-4H-oxazine
• CAS: 491838-93-8
• 化学式: C₂₆H₃₃NO₂
• 分子量: 391.554
• InChiKey: GMJJYEZRIVCQAM-KJUPKDBESA-N

物化性质

• 沸点：
  500.9±60.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,6S)-6-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-3,5-diphenyl-5,6-dihydro-4H-1,2-oxazine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 (2R)-2,4-diphenylbutan-1-amine 、 (S)-2,4-diphenylbutylamine
  参考文献：
  名称：

  Synthesis of Enantioenriched 2-Substituted 4-Phenylbutylamines by Hydrogenolysis of Optically Pure 6-Alkoxy-5,6-dihydro-4H-1,2-oxazines

  摘要：

  Lewis acid promoted exchange of the 6-ethoxy group of 6H-1,2-oxazines 1-3 with (-)-menthol furnished the optically active heterocycles 4-6. Diastereomers 4a and 4b, which could be separated efficiently by chromatography, were excellent substrates for highly diastereoselective conjugate additions of phenyllithium and n-butyllithium, thus providing the enantiopure trans-substituted 1,2-oxazines 7a, 7b, 8a, and 8b in good yields. Exhaustive hydrogenolysis of 7a afforded the primary amine 9 with an enantiomeric excess of 80%, whereas hydrogenolysis of 8a and 8b gave the corresponding amines (R)-11 and (S)-11, respectively, with an ee of more than 90%. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200208)2002:16<2838::aid-ejoc2838>3.0.co;2-o
• 作为产物：
  描述：

  6-乙氧基-3-苯基-6H-1,2-恶嗪 在 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 24.0h， 生成 (5R,6S)-6-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-3,5-diphenyl-5,6-dihydro-4H-1,2-oxazine
  参考文献：
  名称：

  Synthesis of Enantioenriched 2-Substituted 4-Phenylbutylamines by Hydrogenolysis of Optically Pure 6-Alkoxy-5,6-dihydro-4H-1,2-oxazines

  摘要：

  Lewis acid promoted exchange of the 6-ethoxy group of 6H-1,2-oxazines 1-3 with (-)-menthol furnished the optically active heterocycles 4-6. Diastereomers 4a and 4b, which could be separated efficiently by chromatography, were excellent substrates for highly diastereoselective conjugate additions of phenyllithium and n-butyllithium, thus providing the enantiopure trans-substituted 1,2-oxazines 7a, 7b, 8a, and 8b in good yields. Exhaustive hydrogenolysis of 7a afforded the primary amine 9 with an enantiomeric excess of 80%, whereas hydrogenolysis of 8a and 8b gave the corresponding amines (R)-11 and (S)-11, respectively, with an ee of more than 90%. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200208)2002:16<2838::aid-ejoc2838>3.0.co;2-o

文献信息

• Synthesis of Enantioenriched 2-Substituted 4-Phenylbutylamines by Hydrogenolysis of Optically Pure 6-Alkoxy-5,6-dihydro-4H-1,2-oxazines
  作者：Monika Buchholz、Florian Hiller、Hans-Ulrich Reißig

  DOI：10.1002/1099-0690(200208)2002:16<2838::aid-ejoc2838>3.0.co;2-o

  日期：2002.8

  Lewis acid promoted exchange of the 6-ethoxy group of 6H-1,2-oxazines 1-3 with (-)-menthol furnished the optically active heterocycles 4-6. Diastereomers 4a and 4b, which could be separated efficiently by chromatography, were excellent substrates for highly diastereoselective conjugate additions of phenyllithium and n-butyllithium, thus providing the enantiopure trans-substituted 1,2-oxazines 7a, 7b, 8a, and 8b in good yields. Exhaustive hydrogenolysis of 7a afforded the primary amine 9 with an enantiomeric excess of 80%, whereas hydrogenolysis of 8a and 8b gave the corresponding amines (R)-11 and (S)-11, respectively, with an ee of more than 90%. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.