(1R,2S,5S,6R,7S)-5-methyl-5-phenyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one | 528609-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2S,5S,6R,7S)-5-methyl-5-phenyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 528609-85-0
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: CNHUUHIRKGNLGO-OYCUPVHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,5S,6R,7S)-5-methyl-5-phenyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 在 邻二氯苯 作用下， 以83%的产率得到(-)-(S)-5-methyl-5-phenylfuran-2(5H)-one
  参考文献：
  名称：

  Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers

  摘要：

  Continuous nucleophilic addition with several organometallic reagents to tricyclic lactone (-)-1 proceeded diastereoselectively. Newly generated tertiary and quaternary asymmetric centers were controlled by the order in which the nucleophilic reagents were added. Using this methodology, enantiodivergent syntheses of several gamma-substituted butenolides with tertiary and quaternary asymmetric centers were established from a single chiral material. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02711-9
• 作为产物：
  描述：

  (1SR,2RS,6SR,7RS)-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3-one 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 (1R,2S,5S,6R,7S)-5-methyl-5-phenyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
  参考文献：
  名称：

  Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers

  摘要：

  Continuous nucleophilic addition with several organometallic reagents to tricyclic lactone (-)-1 proceeded diastereoselectively. Newly generated tertiary and quaternary asymmetric centers were controlled by the order in which the nucleophilic reagents were added. Using this methodology, enantiodivergent syntheses of several gamma-substituted butenolides with tertiary and quaternary asymmetric centers were established from a single chiral material. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02711-9