N-<(1S)-4-oxocycloheptyl>benzamide | 145192-90-1

• 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: N-<(1S)-4-oxocycloheptyl>benzamide
• 英文别名: N-[(1S)-4-oxocycloheptyl]benzamide
• CAS: 145192-90-1
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: VOYRVCNIQNCLET-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<(1S)-4-oxocycloheptyl>benzamide 在 sodium hydride 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 49.5h， 生成 N-(S)-1,4-Dioxa-spiro[4.6]undec-8-yl-N-methyl-benzamide
  参考文献：
  名称：

  Oxygenation of N-cycloheptylbenzamides with Beauveria sulfurescens

  摘要：

  The oxygenation of several N-cycloheptylbenzamides by fermentation with the fungus Beauveria sulfurescens (ATCC 7159) has been studied. Structures have been determined by chemical and physical methods. Enantioselectivity was observed m the oxygenation process, and the absolute configurations of optically active compounds have been determined by circular dichroism spectroscopy, X-ray crystallography, and chemical correlation. Oxygenation of N-cycloheptylbenzamide (1) gave N-[(1S)-4-oxocycloheptyl]benzamide (2) and N-[(1S,4S)-4-hydroxycycloheptyl]benzamide (5). A reverse of enantioselectivity in the oxygenation process was observed with the substrate N-cycloheptyl-N-methylbenzamide (3), the primary product being N-methyl-N-[(1R)-4-oxocycloheptyl]benzamide (4). Chemical conversion of ketone 2 into N-methyl-N-[(1,S)-4-oxocycloheptyl]benzamide (14) confirmed the enantiomeric relationship of the oxygenation products 2 and 4. Enantiomeric excesses of the oxygenation products were not determined since crystallization was used extensively in the purification of crude products.

  DOI：

  10.1021/jo00052a040
• 作为产物：
  描述：

  N-<(1S,4S)-4-hydroxycycloheptyl>benzamide 在 jones' reagent 作用下， 以 丙酮 为溶剂， 以84%的产率得到N-<(1S)-4-oxocycloheptyl>benzamide
  参考文献：
  名称：

  Oxygenation of N-cycloheptylbenzamides with Beauveria sulfurescens

  摘要：

  The oxygenation of several N-cycloheptylbenzamides by fermentation with the fungus Beauveria sulfurescens (ATCC 7159) has been studied. Structures have been determined by chemical and physical methods. Enantioselectivity was observed m the oxygenation process, and the absolute configurations of optically active compounds have been determined by circular dichroism spectroscopy, X-ray crystallography, and chemical correlation. Oxygenation of N-cycloheptylbenzamide (1) gave N-[(1S)-4-oxocycloheptyl]benzamide (2) and N-[(1S,4S)-4-hydroxycycloheptyl]benzamide (5). A reverse of enantioselectivity in the oxygenation process was observed with the substrate N-cycloheptyl-N-methylbenzamide (3), the primary product being N-methyl-N-[(1R)-4-oxocycloheptyl]benzamide (4). Chemical conversion of ketone 2 into N-methyl-N-[(1,S)-4-oxocycloheptyl]benzamide (14) confirmed the enantiomeric relationship of the oxygenation products 2 and 4. Enantiomeric excesses of the oxygenation products were not determined since crystallization was used extensively in the purification of crude products.

  DOI：

  10.1021/jo00052a040