5-bromo-2,2-dimethyl-1,7-dioxaspiro<5.5>undec-3-ene | 132789-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-bromo-2,2-dimethyl-1,7-dioxaspiro<5.5>undec-3-ene
• 英文别名: (5S,6S)-5-bromo-2,2-dimethyl-1,7-dioxaspiro[5.5]undec-3-ene
• CAS: 132789-42-5；144481-02-7
• 化学式: C₁₁H₁₇BrO₂
• 分子量: 261.159
• InChiKey: SKPOGJFLIPFMII-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-methyl-2-trimethylsilyloxy-4-pentyne 在 Lindlar's catalyst N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 Amberlite resin 、 氢气 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 四氯化碳 为溶剂， 反应 12.5h， 生成 5-bromo-2,2-dimethyl-1,7-dioxaspiro<5.5>undec-3-ene
  参考文献：
  名称：

  Allylic oxidation of unsaturated spiroketals.

  摘要：

  Allylic bromination of the bicyclic spiroketals (4a-c) gave predominantly the axial bromides (6), (9) and (12) which underwent S(N)2 displacement to the equatorial alcohols (7), (11) and (14) respectively using KO2/18-crown-6 in THF/DMSO (10:1).

  DOI：

  10.1016/s0040-4039(00)88531-7

文献信息

• Allylic functionalization of the 1,7-dioxaspiro[5.5]-undec-4-ene and d1,6,8-trioxadispiro[4.1.5.3]-pentadec-13-ene ring systems.
  作者：Margaret A. Brimble、Michael K. Edmonds、Geoffrey M. Williams

  DOI：10.1016/s0040-4020(01)88235-1

  日期：1992.1

  Allylic bromination of the bicyclic spiroacetals 5, 6 and 7 gave predominantly the axial bromides 15, 21 and 23 which underwent S(N)2 displacement to the equatorial alcohols 17, 22 and 25 respectively, using potassium superoxide and 18-crown-6 in THF/DMSO (10:1). Allylic bromination of the cis-bis-spiroacetal 26 gave predominantly the rearranged allylic bromide 29 which afforded alcohols 30 and 31 resulting from both S(N)2' and S(N)2 displacement upon treatment with potassium superoxide. Bromination of the trans-bis-spiroacetal 27 afforded a complex mixture from which only the non-rearranged bromide 34 could be isolated. This bromide 34 afforded the axial alcohol 37 upon treatment with potassium superoxide.
• BRIMBLE, MARGARET A.;EDMONDS, MICHAEL K.;WILLIAMS, GEOFFREY M., TETRAHEDRON LETT., 31,(1990) N1, C. 7509-7512
  作者：BRIMBLE, MARGARET A.、EDMONDS, MICHAEL K.、WILLIAMS, GEOFFREY M.

  DOI：——

  日期：——
• Allylic oxidation of unsaturated spiroketals.
  作者：Margaret A Brimble、Michael K Edmonds、Geoffrey M Williams

  DOI：10.1016/s0040-4039(00)88531-7

  日期：1990.1

  Allylic bromination of the bicyclic spiroketals (4a-c) gave predominantly the axial bromides (6), (9) and (12) which underwent S(N)2 displacement to the equatorial alcohols (7), (11) and (14) respectively using KO2/18-crown-6 in THF/DMSO (10:1).

表征谱图