(1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene-4-one | 1236768-81-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene-4-one
• 英文别名: (1R,5R,7S)-7-(iodomethyl)-4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-2-one
• CAS: 1236768-81-2
• 化学式: C₁₀H₁₃IO₂
• 分子量: 292.117
• InChiKey: DPAMRJLZJRFANZ-FXBDTBDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene-4-one 在 臭氧 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  New orthogonally functionalized synthetic blocks from R-(−)-carvone

  摘要：

  The intramolecular cyclization of (-)-cis-carveol under iodine treatment afforded (1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene that was subjected to allyl oxydation with the complex CrO3DMP giving a synthetically valuable building block, (1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene-4-one. In the latter the double bond was cleaved by ozonization to obtain the expected trioxo derivative, and the subsequent ozonolysis of its enol form provided a multiple functionalized tetrahydrofuran derivative.

  DOI：

  10.1134/s107042801005012x
• 作为产物：
  描述：

  (1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene 在 chromium(VI) oxide 、 1,5-二甲基-1H-吡唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以65%的产率得到(1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene-4-one
  参考文献：
  名称：

  New orthogonally functionalized synthetic blocks from R-(−)-carvone

  摘要：

  The intramolecular cyclization of (-)-cis-carveol under iodine treatment afforded (1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene that was subjected to allyl oxydation with the complex CrO3DMP giving a synthetically valuable building block, (1R,5R,6S)-6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene-4-one. In the latter the double bond was cleaved by ozonization to obtain the expected trioxo derivative, and the subsequent ozonolysis of its enol form provided a multiple functionalized tetrahydrofuran derivative.

  DOI：

  10.1134/s107042801005012x