5-fluoro-9-methylenehomoadamantane | 207604-96-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 5-fluoro-9-methylenehomoadamantane
• 英文别名: 3-Fluoro-9-methylidenetricyclo[4.3.1.13,8]undecane
• CAS: 207604-96-4
• 化学式: C₁₂H₁₇F
• 分子量: 180.265
• InChiKey: DCSCBUNDDXGPPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-fluoro-9-methylenehomoadamantane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 Z-5-fluoro-9-methylenehomoadamantane epoxide 、 E-5-fluoro-9-methylenehomoadamantane epoxide
  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：

  3-hydroxyhomoadamantan-9-one ethylene ketal 在 吡啶 、 正丁基锂 、 ammonium bifluoride 、 poly-hydrogen fluoride 作用下， 反应 2.83h， 生成 5-fluoro-9-methylenehomoadamantane
  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

文献信息

• Effect of Remote Substitution on Face Selection in Addition Reactions of Nor- and Homoadamantan-9-ones and of Several Analogues
  作者：Mira Kaselj、Elena M. Gonikberg、William J. le Noble

  DOI：10.1021/jo9718197

  日期：1998.5.1

  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.