N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-7-methoxynaphthalene-1-carboxamide | 161693-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-7-methoxynaphthalene-1-carboxamide
• CAS: 161693-46-5
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: ZEBQBTRTPPVRCJ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-7-methoxynaphthalene-1-carboxamide 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 四丁基氟化铵 、 氢气 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 111.58h， 生成 (R)-7-methoxy-1-methyl-1-vinyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Asymmetric Synthesis of the Key Intermediates Leading to (-)-Aphanorphine and (-)-Eptazocine

  摘要：

  The asymmetric syntheses of two key intermediates, 8 and 15, in >99% ee are reported. These compounds are prepared by diastereofacial addition of lithiodimethylphenylsilane to chiral naphthyloxazolines followed by methyl iodide trapping. The two stereocenters are formed in greater than 95% ds, and the silyl center is subsequently removed to give the 1,1-disubstituted tetralins 8, 9, or 12. These chiral substances are readily transformed into the titled compounds as described in the literature. The absolute configuration of these intermediates has been confirmed by X-ray analysis and corrects an earlier misassignment.

  DOI：

  10.1021/jo00110a033
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 1,3-双(二苯基膦)丙烷 、 palladium diacetate 吡啶 、 盐酸 、 溴 、 lithium carbonate 、 三乙胺 、 lithium bromide 作用下， 以 乙醚 、 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.83h， 生成 N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-7-methoxynaphthalene-1-carboxamide
  参考文献：
  名称：

  Asymmetric Synthesis of the Key Intermediates Leading to (-)-Aphanorphine and (-)-Eptazocine

  摘要：

  The asymmetric syntheses of two key intermediates, 8 and 15, in >99% ee are reported. These compounds are prepared by diastereofacial addition of lithiodimethylphenylsilane to chiral naphthyloxazolines followed by methyl iodide trapping. The two stereocenters are formed in greater than 95% ds, and the silyl center is subsequently removed to give the 1,1-disubstituted tetralins 8, 9, or 12. These chiral substances are readily transformed into the titled compounds as described in the literature. The absolute configuration of these intermediates has been confirmed by X-ray analysis and corrects an earlier misassignment.

  DOI：

  10.1021/jo00110a033

文献信息

• Asymmetric Synthesis of the Key Intermediates Leading to (-)-Aphanorphine and (-)-Eptazocine
  作者：Alison N. Hulme、Steven S. Henry、A. I. Meyers

  DOI：10.1021/jo00110a033

  日期：1995.3

  The asymmetric syntheses of two key intermediates, 8 and 15, in >99% ee are reported. These compounds are prepared by diastereofacial addition of lithiodimethylphenylsilane to chiral naphthyloxazolines followed by methyl iodide trapping. The two stereocenters are formed in greater than 95% ds, and the silyl center is subsequently removed to give the 1,1-disubstituted tetralins 8, 9, or 12. These chiral substances are readily transformed into the titled compounds as described in the literature. The absolute configuration of these intermediates has been confirmed by X-ray analysis and corrects an earlier misassignment.