1-bromo-9-oxo-noradamantan-3-carboxylic acid ethylene ketal | 207605-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-9-oxo-noradamantan-3-carboxylic acid ethylene ketal
• 英文别名: 1'-Bromospiro[1,3-dioxolane-2,9'-tricyclo[3.3.1.03,7]nonane]-3'-carboxylic acid
• CAS: 207605-01-4
• 化学式: C₁₂H₁₅BrO₄
• 分子量: 303.153
• InChiKey: GHWZZARKCFFLAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-bromo-9-oxo-noradamantan-3-carboxylic acid ethylene ketal 在 palladium on activated charcoal 氢氧化钾 、 sodium tetrahydroborate 、 氢气 、 溴 、 silver fluoride 、 mercury(II) oxide 、 二溴甲烷 作用下， 以 甲醇 、 环己烷 为溶剂， 25.0 ℃ 、151.99 kPa 条件下， 反应 127.5h， 生成 Z-3-fluoronoradamantan-9-ol
  参考文献：
  名称：

  Effect of Remote Substitution on Face Selection in Addition Reactions of Nor- and Homoadamantan-9-ones and of Several Analogues

  摘要：

  The effects of 3-halo substitution on face selection in borohydride reductions of both nor-and homoadamantan-9-ones l-X and 3-X. respectively, have been compared with those of 5-halo substitution in the parent 5-haloadamantan-2-ones 2-X, The differences between the product ratios in these three compounds are small, but the selectivity of 2-X is somewhat larger than that of either of the homologues. This is also true of the corresponding aza-and diazaadamantanones, and of an electrophilic addition. It is concluded that the approach angle of the reagent is not a sensitive variable in addition reactions of cyclohexanone and its derivatives, and that well-aligned antiperiplanar bonds are preferred to achieve maximal remote substituent induced selectivities.

  DOI：

  10.1021/jo9718197
• 作为产物：
  描述：

  1-bromo-9-oxo-noradamantan-3-carboxylic acid 、 乙二醇 在 zinc(II) chloride 作用下， 反应 0.02h， 以85%的产率得到1-bromo-9-oxo-noradamantan-3-carboxylic acid ethylene ketal
  参考文献：
  名称：

  Effect of Remote Substitution on Face Selection in Addition Reactions of Nor- and Homoadamantan-9-ones and of Several Analogues

  摘要：

  The effects of 3-halo substitution on face selection in borohydride reductions of both nor-and homoadamantan-9-ones l-X and 3-X. respectively, have been compared with those of 5-halo substitution in the parent 5-haloadamantan-2-ones 2-X, The differences between the product ratios in these three compounds are small, but the selectivity of 2-X is somewhat larger than that of either of the homologues. This is also true of the corresponding aza-and diazaadamantanones, and of an electrophilic addition. It is concluded that the approach angle of the reagent is not a sensitive variable in addition reactions of cyclohexanone and its derivatives, and that well-aligned antiperiplanar bonds are preferred to achieve maximal remote substituent induced selectivities.

  DOI：

  10.1021/jo9718197