4-hydroxy-4-(hydroxymethyl)-1-(p-toluenesulfonyl)piperidine | 145385-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxy-4-(hydroxymethyl)-1-(p-toluenesulfonyl)piperidine
• 英文别名: 4-(Hydroxymethyl)-1-(4-methylphenyl)sulfonylpiperidin-4-ol
• CAS: 145385-45-1
• 化学式: C₁₃H₁₉NO₄S
• 分子量: 285.364
• InChiKey: SBFQQKSQRBOGOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-methylene-1-tosylpiperidine 以20%的产率得到4-hydroxy-4-(hydroxymethyl)-1-(p-toluenesulfonyl)piperidine
  参考文献：
  名称：

  Selective oxygenation of adamantanes and other substrates by Beauveria sulfurescens

  摘要：

  Oxygenation of N-(2-adamantyl)benzamide (7) with the fungus Beauveria sulfurescens (ATCC 7159) gave 4beta-benzamidoadamantan-1-ol (8), whose structure was determined by X-ray crystallography. Oxygenation of N-methyl-N-(4-methyleneadamant-1-yl)benzamide (9) gave two products, the beta-epoxide 10 and the 5-hydroxy beta-epoxide 11, the latter structure determined by X-ray crystallography. Oxygenation of 4-methylene-l-(p-toluenesulfonyl)piperidine (12) gave 4-hydroxy-4-(hydroxymethyl)-l-(p-toluenesulfonyl)piperidine (14) and of 4-piperidinoacetophenone (13) gave 4-(4-hydroxypiperidino)acetophenone (15).

  DOI：

  10.1021/jo00052a039

文献信息

• Selective oxygenation of adamantanes and other substrates by Beauveria sulfurescens
  作者：Roy A. Johnson、Milton E. Herr、Herbert C. Murray、Constance G. Chidester、Fusen Han

  DOI：10.1021/jo00052a039

  日期：1992.12

  Oxygenation of N-(2-adamantyl)benzamide (7) with the fungus Beauveria sulfurescens (ATCC 7159) gave 4beta-benzamidoadamantan-1-ol (8), whose structure was determined by X-ray crystallography. Oxygenation of N-methyl-N-(4-methyleneadamant-1-yl)benzamide (9) gave two products, the beta-epoxide 10 and the 5-hydroxy beta-epoxide 11, the latter structure determined by X-ray crystallography. Oxygenation of 4-methylene-l-(p-toluenesulfonyl)piperidine (12) gave 4-hydroxy-4-(hydroxymethyl)-l-(p-toluenesulfonyl)piperidine (14) and of 4-piperidinoacetophenone (13) gave 4-(4-hydroxypiperidino)acetophenone (15).