7-(2-bromomethyl)-7-hydroxyspiro[4.5]decan-6-one | 949530-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(2-bromomethyl)-7-hydroxyspiro[4.5]decan-6-one
• 英文别名: 9-(2-Bromoethyl)-9-hydroxyspiro[4.5]decan-10-one
• CAS: 949530-19-2
• 化学式: C₁₂H₁₉BrO₂
• 分子量: 275.186
• InChiKey: PTNDXHWDDXELAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(2-bromomethyl)-7-hydroxyspiro[4.5]decan-6-one 在 sodium hydroxide 、 三氟甲磺酸酐 、 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 2',3',5',6'-tetrahydrospiro[cyclopentane-1,7'-cyclopenta[b]pyridine]-4'(1'H)-one
  参考文献：
  名称：

  Fragmentation of Nitrone Triflates to 9-Membered Rings

  摘要：

  A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

  DOI：

  10.1021/ol071049d
• 作为产物：
  描述：

  螺[4,5]癸烷-6-酮 在 potassium tert-butylate 、 溴 、 双(三甲基硅烷基)氨基钾 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 48.25h， 生成 7-(2-bromomethyl)-7-hydroxyspiro[4.5]decan-6-one
  参考文献：
  名称：

  Fragmentation of Nitrone Triflates to 9-Membered Rings

  摘要：

  A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

  DOI：

  10.1021/ol071049d