2-(iodomethyl)-1-oxaspiro<2.4>heptane | 139367-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 2-(iodomethyl)-1-oxaspiro<2.4>heptane
• 英文别名: 2-(Iodomethyl)-1-oxaspiro[2.4]heptane
• CAS: 139367-25-2
• 化学式: C₇H₁₁IO
• 分子量: 238.068
• InChiKey: YLGVAEZTYIKXQC-UHFFFAOYSA-N

物化性质

• 沸点：
  259.3±13.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(iodomethyl)-1-oxaspiro<2.4>heptane 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以9%的产率得到环庚酮
  参考文献：
  名称：

  1-Alkenylcycloalkoxy radical chemistry. A two-carbon ring expansion methodology

  摘要：

  The exploitation of alkoxy radicals derived from 1-ethenylcycloalkanols for use in a two-carbon ring expansion protocol was proposed. Direct one-pot alkoxy radical-mediated fragmentation-cyclization was not feasible since the reactive intermediate was quenched by iodine in the reaction mixture. However, via the use of iodo epoxides 3, the tandem fragmentation-cyclization sequence could be accomplished. This afforded ring-expanded products via an endo mode of cyclization, although in one example product from an exo mode of cyclization was also isolated. This methodology was shown to be valid for large ring compounds as well. The intermediary of iodo epoxides 3 also afforded improved yields as compared to the direct cyclization of iodo enones 4. These results are the first examples of radical cyclization to medium-sized carbocycles.

  DOI：

  10.1021/jo00057a039
• 作为产物：
  描述：

  1-乙烯基环戊烷-1-醇 在 碘苯二乙酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以54%的产率得到7-iodohept-1-en-3-one
  参考文献：
  名称：

  碘代苯二乙酸酯在合成α-碘环氧化物中的用途

  摘要：

  在光化学条件下，将叔烯丙醇暴露于碘代苯二乙酸-碘会导致以高收率形成相应的α-碘环氧化物。

  DOI：

  10.1016/0040-4039(91)80515-8

文献信息

• Use of iodobenzene diacetate for the synthesis of α-iodoepoxides
  作者：Paul Galatsis、Scott D. Millan

  DOI：10.1016/0040-4039(91)80515-8

  日期：1991.12

  Exposure of tertiary allylic alcohols to iodobenzene diacetate-iodine under photochemical conditions results in formation of the corresponding α-iodoepoxides in good yield.

  在光化学条件下，将叔烯丙醇暴露于碘代苯二乙酸-碘会导致以高收率形成相应的α-碘环氧化物。
• 1-Alkenylcycloalkoxy radical chemistry. A two-carbon ring expansion methodology
  作者：Paul Galatsis、Scott D. Millan、Tim Faber

  DOI：10.1021/jo00057a039

  日期：1993.2

  The exploitation of alkoxy radicals derived from 1-ethenylcycloalkanols for use in a two-carbon ring expansion protocol was proposed. Direct one-pot alkoxy radical-mediated fragmentation-cyclization was not feasible since the reactive intermediate was quenched by iodine in the reaction mixture. However, via the use of iodo epoxides 3, the tandem fragmentation-cyclization sequence could be accomplished. This afforded ring-expanded products via an endo mode of cyclization, although in one example product from an exo mode of cyclization was also isolated. This methodology was shown to be valid for large ring compounds as well. The intermediary of iodo epoxides 3 also afforded improved yields as compared to the direct cyclization of iodo enones 4. These results are the first examples of radical cyclization to medium-sized carbocycles.