(1S,2R,8S,9R,10R)-10-Phenyl-6-oxa-3-aza-tricyclo[7.2.1.0^2,8]dodecan-4-one

• 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: (1S,2R,8S,9R,10R)-10-Phenyl-6-oxa-3-aza-tricyclo[7.2.1.0^2,8]dodecan-4-one
• 英文别名: rel-(5aR,6S,7S,9R,9aS)-7-phenyloctahydro-6,9-methano-4,1-benzoxazepin-2-one；(1S,2R,8S,9R,10R)-10-phenyl-6-oxa-3-azatricyclo[7.2.1.02,8]dodecan-4-one
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: MBBJJZHMWKBYMA-YMSVYLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,2R,3S,4R,6S)-3-Amino-6-phenyl-bicyclo[2.2.1]heptane-2-carboxylic acid 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 9.0h， 生成 (1S,2R,8S,9R,10R)-10-Phenyl-6-oxa-3-aza-tricyclo[7.2.1.0^2,8]dodecan-4-one
  参考文献：
  名称：

  Regioselective Synthesis of 3-endo-Hydroxymethyl-5-exo-phenylbicyclo[2.2.1]heptan-2-endo-amine and its Transformation into Saturated or Partially Saturated Di-endo-fused Heterocycles.

  摘要：

  AlCl3-catalysed addition of benzene to di-endo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid (1) and subsequent treatment with acetic anhydride yields 5-exo-phenylbicyclo[2.2.1]heptane-2,3-di-endo-carboxylic anhydride (2). 3-endo-Hydroxymethyl-5-exo-phenylbicyclo[2.2.1]heptane-2-endo-amine (4) was prepared by LAH reduction of the beta-amino acid 3 obtained by Hofmann degradation of the carboxy amide prepared from 2. Reaction of 4 with ethyl chloroformate or with CS2-NaOH-Pb2+ furnished the methylene-bridged hexahydro-3,1-benzoxazin-2(1H)-one (5) or -benzoxazine-2(1H)-thione (6). With ethyl chloroacetate or 2-chloropropionate, 4 gave the tricyclic oxazepinones 7 and 8. The norbornane 1,3-amino alcohol 4 was transformed with phenyl isothiocyanate into the phenylimino-1,3-oxazine 9 and -thiazine 10. The cyclizations of 4 with 2-(p-methylbenzoyl)benzoic acid or cis-2-p-chlorobenzoyl-1-cyclohexanecarboxylic acid led to the methylene-bridged isoindolo[2,1-a][3,1]benzoxazines 11 and 12. With p-chlorobenzimidate, the di-endo-5,8-methano-4H-3,1-benzoxazine 13 was obtained, which was converted with dichloroacetic acid-triethylamine into the isomeric azetidinones 14 and 15, or with benzonitrile oxide to the methano-1,2,4-oxadiazolo[4,5-a][3,1]benzoxazine (16). The stereostructures of the new compounds were elucidated by NMR spectroscopy and for 13 also by X-ray diffractometry.

  DOI：

  10.3891/acta.chem.scand.50-0922

表征谱图