3-hydroxyhomoadamantan-9-one ethylene ketal | 207605-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxyhomoadamantan-9-one ethylene ketal
• 英文别名: Spiro[1,3-dioxolane-2,9'-tricyclo[4.3.1.13,8]undecane]-3'-ol
• CAS: 207605-03-6
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: GYTRZYYETGOWLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxyhomoadamantan-9-one ethylene ketal 在 吡啶 、 sodium tetrahydroborate 、 ammonium bifluoride 、 poly-hydrogen fluoride 作用下， 以 甲醇 为溶剂， 反应 3.33h， 生成 Z-5-fluorohomoadamantan-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：

  5-(tosyloxymethyl)adamantan-2-one ethylene ketal 在 2,2,2-三氟乙醇 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 15.0h， 生成 5-(hydroxymethyl)adamantan-2-one ethylene ketal 、 3-hydroxyhomoadamantan-7-one ethylene ketal 、 3-hydroxyhomoadamantan-9-one 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

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.