(2S,5R)-5-acetyl-2-iodomethyl-2-methyldihydrofuran-3-one | 1236768-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2S,5R)-5-acetyl-2-iodomethyl-2-methyldihydrofuran-3-one
• 英文别名: (2s,5r)-5-Acetyl-2-iodomethyl-2-methyl-dihydrofuran-3-one；(2S,5R)-5-acetyl-2-(iodomethyl)-2-methyloxolan-3-one
• CAS: 1236768-85-6
• 化学式: C₈H₁₁IO₃
• 分子量: 282.078
• InChiKey: SFXXAFSPCHOTBQ-HTRCEHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,5R)-5-acetyl-2-iodomethyl-2-methyldihydrofuran-3-ylidenehydroxyacetaldehyde 在 臭氧 作用下， 以 甲醇 为溶剂， 以60%的产率得到(2S,5R)-5-acetyl-2-iodomethyl-2-methyldihydrofuran-3-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

文献信息

• Chiral building blocks from R-(–)-carvone: N-bromosuccinimidemediated addition–sceletal rearrangement of (–)-cis-carveol
  作者：Ruslan F. Valeev、Nataliya K. Selezneva、Zoya A. Starikova、Evgenii Yu. Pankrat’ev、Mansur S. Miftakhov

  DOI：10.1016/j.mencom.2010.03.004

  日期：2010.3

  Synthetically valuable bicyclic blocks 5, 7 and 9 were prepared by the oxidative cleavage of the double bond of 4 with the RuCl3- NaIO4 system and O-3.