(6R,8R)-6-iodo-8-propyloxocan-2-one | 945772-75-8

• 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: (6R,8R)-6-iodo-8-propyloxocan-2-one
• CAS: 945772-75-8
• 化学式: C₁₀H₁₇IO₂
• 分子量: 296.148
• InChiKey: PYCIPGKMEJNUDL-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (6R,8R)-6-iodo-8-propyloxocan-2-one 在 Lindlar's catalyst sodium azide 、 氢气 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 (6S)-6-[(2R)-2-hydroxypentyl]piperidin-2-one
  参考文献：
  名称：

  Cyclopentanone Ring Expansion Leading to Functionalized δ-Lactams:  Short Synthesis of Simple Sedum Alkaloids

  摘要：

  Monosubstituted epoxides react with (cyclopentenyloxy)trimethylsilane to afford, after subsequent oxidative fragmentation, a pair of diastereomeric 8-membered iodolactones. When these lactones are separately treated with sodium azide, followed by reduction over Lindlar's catalyst, lactone ring contraction yields 6-membered monosubstituted lactams. When (R)-1,2-epoxypentane is used in this 5 + 3 - 2 overall ring expansion sequence, one final step involving delta-lactam to piperidine reduction yields natural (-)-halosaline and (-)-epihalosaline in five steps and 12% and 23% overall yields, respectively.

  DOI：

  10.1021/ol070960r
• 作为产物：
  描述：

  (R)-1,2-环氧基戊烷 在 碘苯二乙酸 、 甲基锂 、 碘 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.08h， 生成 (6R,8R)-6-iodo-8-propyloxocan-2-one
  参考文献：
  名称：

  Cyclopentanone Ring Expansion Leading to Functionalized δ-Lactams:  Short Synthesis of Simple Sedum Alkaloids

  摘要：

  Monosubstituted epoxides react with (cyclopentenyloxy)trimethylsilane to afford, after subsequent oxidative fragmentation, a pair of diastereomeric 8-membered iodolactones. When these lactones are separately treated with sodium azide, followed by reduction over Lindlar's catalyst, lactone ring contraction yields 6-membered monosubstituted lactams. When (R)-1,2-epoxypentane is used in this 5 + 3 - 2 overall ring expansion sequence, one final step involving delta-lactam to piperidine reduction yields natural (-)-halosaline and (-)-epihalosaline in five steps and 12% and 23% overall yields, respectively.

  DOI：

  10.1021/ol070960r