cis-3-(iodomethyl)-3,5-dimethyl-2,6-dioxacyclohexanone | 83134-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: cis-3-(iodomethyl)-3,5-dimethyl-2,6-dioxacyclohexanone
• 英文别名: 3-(Iodomethyl)-3,5-dimethyl-2,6-dioxacyclohexanone
• CAS: 83134-84-3
• 化学式: C₇H₁₁IO₃
• 分子量: 270.067
• InChiKey: QBOBOVXKLFEYSJ-FSPLSTOPSA-N

物化性质

• 沸点：
  337.5±15.0 °C(Predicted)
• 密度：
  1.653±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis-3-(iodomethyl)-3,5-dimethyl-2,6-dioxacyclohexanone 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到threo-4,5-epoxy-4-methyl-2-pentanol
  参考文献：
  名称：

  Synthesis, Analysis, and Field Activity of Sordidin, a Male-Produced Aggregation Pheromone of the Banana Weevil, Cosmopolites sordidus

  摘要：

  An efficient synthesis of the diastereoisomers of sordidin (1), a male-produced aggregation pheromone of Cosmopolites sordidus, has been developed from commercially available 4-methylpent-4-en-2-ol (2). Preparation of exo-beta-sordidin (1a) and endo-beta-sordidin (1b) is via the anti epoxide, 4d, which is derived via iodocarbonation of 2, The endo-alpha-sordidin (1c) and exo-alpha-sordidin (1d) are prepared from the corresponding syn epoxide, which is available via stereo-controlled epoxidation of the triisopropylsilyloxy derivative, 3b. Silyloxy derivatives of the epoxides, 4, efficiently alkylate the anions of N-cyclohexyldiethylketimine (6a) and 3-pentanone N,N-dimethylhydrazone (6b). Acidic work-up of these alkylation reactions promotes cyclization to give 1, Gram quantities of 1a-1d, 1a + 1b and 1c + 1d have been prepared by this route. In field tests in a banana plantation in Costa Rica, compounds 1a-1d significantly increased capture rates of standard pseudostem traps. Comparable numbers of adults were attracted to pseudostem traps baited with the major naturally occurring isomers of sordidin 1c + 1d or 1a-1d, Although addition of the minor naturally occurring isomers of sordidin (1a and 1b) to pseudostem traps increased capture rates above controls, these compounds did not increase attraction of pseudostem traps to the same extent as 1a-1d. In comparison tests with conventional pseudostem traps, significantly more adults were trapped in water-containing pitfall traps baited with 1a-1d.

  DOI：

  10.1023/b:joec.0000006392.54376.0e
• 作为产物：
  描述：

  4-甲基-4-戊烯-2-醇 、 二氧化碳 生成 cis-3-(iodomethyl)-3,5-dimethyl-2,6-dioxacyclohexanone 、 trans-3-(iodomethyl)-3,5-dimethyl-2,6-dioxacyclohexanone
  参考文献：
  名称：

  Regio- and stereocontrolled synthesis of epoxy alcohols and triols from allylic and homoallylic alcohols via iodocarbonates

  摘要：

  DOI：

  10.1021/jo00145a004