(1S,2R,8R)-1-iodo-2-iodomethyl-11,11-dimethyl-3-oxabicyclo[6.2.1]undecane-4,6-dione | 372955-46-9

• 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: (1S,2R,8R)-1-iodo-2-iodomethyl-11,11-dimethyl-3-oxabicyclo[6.2.1]undecane-4,6-dione
• 英文别名: (1S,2R,8R)-1-iodo-2-(iodomethyl)-11,11-dimethyl-3-oxabicyclo[6.2.1]undecane-4,6-dione
• CAS: 372955-46-9
• 化学式: C₁₃H₁₈I₂O₃
• 分子量: 476.093
• InChiKey: CACBUSCYTZDOLW-ZDSQKVDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,8R)-1-iodo-2-iodomethyl-11,11-dimethyl-3-oxabicyclo[6.2.1]undecane-4,6-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以68%的产率得到(1S,2R,8R)-2-hydroxymethyl-1-iodo-11,11-dimethyl-3-oxabicyclo[6.2.1]undecane-4,6-dione
  参考文献：
  名称：

  摘要：

  The Reformatsky reaction of bornanic enone (10-nor-1-vinylcamphor) with ethyl iodoacetate followed by iodocyclization afforded tricyclic iodolactone. Fragmentation of the latter initiated by HgO-I-2 gave rise to bicyclic iodoxolactone. Attempts to perform cyclization of this iodoxolactone analogously to intramolecular alkylation of CH-acids with halogen-containing electrophiles failed.

  DOI：

  10.1023/a:1011360828286
• 作为产物：
  描述：

  (-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-carboxymethylbicyclo[2.2.1]heptane 在 碘 、 potassium iodide 、 mercury(II) oxide 作用下， 以 四氯化碳 、 水 为溶剂， 反应 0.58h， 生成 (1S,2R,8R)-1-iodo-2-iodomethyl-11,11-dimethyl-3-oxabicyclo[6.2.1]undecane-4,6-dione
  参考文献：
  名称：

  摘要：

  The Reformatsky reaction of bornanic enone (10-nor-1-vinylcamphor) with ethyl iodoacetate followed by iodocyclization afforded tricyclic iodolactone. Fragmentation of the latter initiated by HgO-I-2 gave rise to bicyclic iodoxolactone. Attempts to perform cyclization of this iodoxolactone analogously to intramolecular alkylation of CH-acids with halogen-containing electrophiles failed.

  DOI：

  10.1023/a:1011360828286