2-<5,7-Bis(p-nitrophenyl)adamantyl> tosylate | 154158-58-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2-<5,7-Bis(p-nitrophenyl)adamantyl> tosylate
• 英文别名: [5,7-Bis(4-nitrophenyl)-2-adamantyl] 4-methylbenzenesulfonate
• CAS: 154158-58-4
• 化学式: C₂₉H₂₈N₂O₇S
• 分子量: 548.617
• InChiKey: ILSMMRBXKLZQFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-<5,7-Bis(p-nitrophenyl)adamantyl> tosylate 在 platinum on activated charcoal 氢气 作用下， 以 苯 为溶剂， 生成 、 (Z)-2-<5-(p-Aminophenyl)-7-(p-nitrophenyl)adamantyl> tosylate
  参考文献：
  名称：

  Face selection in the reduction of p,p'-disubstituted 5,7-diphenyl-2-adamantanones and hydrolysis of the corresponding 2-adamantyl tosylates

  摘要：

  The reduction of 5,7-diphenyl-2-adamantanone with sodium borohydride in 2-propanol is affected by the introduction of a p-nitro substituent in one of the rings: the E-alcohol is obtained in small but easily measurable excess of 1.30:1. Conversely, the introduction of a p-amino group leads to an excess of Z-isomer by roughly the same factor (1.28). When both substituents are present, they evidently cooperate to produce a ratio of 1.64. The tosylates of the alcohols were prepared and their solvolysis rates measured in 3% aqueous hexafluoro-2-propanol and compared with those of the parent and p-substituted 5-phenyl-2-adamantyl tosylates. Additivity of substituent effects was again observed, but the p-aminophenyl group in these reactions was deactivating compared to phenyl, presumably due to II-bonding and/or protonation of the amino group in the acidic medium.

  DOI：

  10.1021/jo00080a012
• 作为产物：
  描述：

  5,7-Diphenyladamantan-2-yl tosylate 在 硝酸 作用下， 以 硝基甲烷 、 乙酸酐 为溶剂， 反应 10.0h， 以53.9%的产率得到2-<5,7-Bis(p-nitrophenyl)adamantyl> tosylate
  参考文献：
  名称：

  Face selection in the reduction of p,p'-disubstituted 5,7-diphenyl-2-adamantanones and hydrolysis of the corresponding 2-adamantyl tosylates

  摘要：

  The reduction of 5,7-diphenyl-2-adamantanone with sodium borohydride in 2-propanol is affected by the introduction of a p-nitro substituent in one of the rings: the E-alcohol is obtained in small but easily measurable excess of 1.30:1. Conversely, the introduction of a p-amino group leads to an excess of Z-isomer by roughly the same factor (1.28). When both substituents are present, they evidently cooperate to produce a ratio of 1.64. The tosylates of the alcohols were prepared and their solvolysis rates measured in 3% aqueous hexafluoro-2-propanol and compared with those of the parent and p-substituted 5-phenyl-2-adamantyl tosylates. Additivity of substituent effects was again observed, but the p-aminophenyl group in these reactions was deactivating compared to phenyl, presumably due to II-bonding and/or protonation of the amino group in the acidic medium.

  DOI：

  10.1021/jo00080a012

文献信息

• Face selection in the reduction of p,p'-disubstituted 5,7-diphenyl-2-adamantanones and hydrolysis of the corresponding 2-adamantyl tosylates
  作者：In H. Song、William J. le Noble

  DOI：10.1021/jo00080a012

  日期：1994.1

  The reduction of 5,7-diphenyl-2-adamantanone with sodium borohydride in 2-propanol is affected by the introduction of a p-nitro substituent in one of the rings: the E-alcohol is obtained in small but easily measurable excess of 1.30:1. Conversely, the introduction of a p-amino group leads to an excess of Z-isomer by roughly the same factor (1.28). When both substituents are present, they evidently cooperate to produce a ratio of 1.64. The tosylates of the alcohols were prepared and their solvolysis rates measured in 3% aqueous hexafluoro-2-propanol and compared with those of the parent and p-substituted 5-phenyl-2-adamantyl tosylates. Additivity of substituent effects was again observed, but the p-aminophenyl group in these reactions was deactivating compared to phenyl, presumably due to II-bonding and/or protonation of the amino group in the acidic medium.