(3aR,4S,7R,7aS)-3-hydroxy-2-[(1S)-1-phenylethyl]-2,3,3a,4,7,7a-hexahydro-1H-4,7-epoxyinden-1-one | 1314517-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3aR,4S,7R,7aS)-3-hydroxy-2-[(1S)-1-phenylethyl]-2,3,3a,4,7,7a-hexahydro-1H-4,7-epoxyinden-1-one
• CAS: 1314517-63-9
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: BARUIUSLNROINK-BMJAIKTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S)-1-phenylethylammonium (+/-)-3-{[(1S)-1-phenyl-ethyl]aminocarbonyl}-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3aR,4S,7R,7aS)-3-hydroxy-2-[(1S)-1-phenylethyl]-2,3,3a,4,7,7a-hexahydro-1H-4,7-epoxyinden-1-one 、 (3aS,4R,7S,7aR)-3-hydroxy-2-[(1S)-1-phenylethyl]-2,3,3a,4,7,7a-hexahydro-1H-4,7-epoxyinden-1-one 、 2-[(1S)-1-phenylethyl]-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3-dione 、 (3aS,4S,7R,7aS)-2-[(1S)-1-phenylethyl]-3-{[(1S)-1-phenylethyl]amino}-2,3,3a,4,7,7a-hexahydro-1H-4,7-epoxyisoindole-1-one 、 (3aR,4R,7S,7aR)-2-[(1S)-1-phenylethyl]-3-{[(1S)-1-phenylethyl]amino}-2,3,3a,4,7,7a-hexahydro-1H-4,7-epoxyisoindole-1-one
  参考文献：
  名称：

  Characteristic features of reduction with i-Bu2AlH of products of ring opening with (−)-α-methylbenzylamine of (3aS,4R,7R,7aS)-3a,4,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-1,3-dione

  摘要：

  A special procedure of synthesis was developed for amidoaminals of atypical topology through a reduction with i-Bu2AlH of primary products of thermodynamical opening of (3aS,4R,7R,7aS)-3a,4,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-1,3-dione at treating with (-)-alpha-methylbenzylamine. Characteristic spectral criteria are described for assignment of diastereomeric compounds; possible routes of reaction stages are considered.

  DOI：

  10.1134/s1070428011050101