N-acetylazacyclohexan-4-one tosylhydrazone | 4305-25-3

• 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-acetylazacyclohexan-4-one tosylhydrazone
• 英文别名: 1-Acetyl-piperid-4-on-tosylhydrazon；N-[(1-acetylpiperidin-4-ylidene)amino]-4-methylbenzenesulfonamide
• CAS: 4305-25-3
• 化学式: C₁₄H₁₉N₃O₃S
• 分子量: 309.389
• InChiKey: ZRLKJOYGMJHOEE-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  514.5±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-acetylazacyclohexan-4-one tosylhydrazone 在 硼氘化钠 、 重水 作用下， 以 氘代甲醇-d 为溶剂， 反应 24.0h， 以86%的产率得到N-acetyl-4,4-dideuterioazacyclohexane
  参考文献：
  名称：

  Effects of substitution on nitrogen on barriers to rotation of amides. 2—Evaluation of the importance of resonance effects

  摘要：

  AbstractAnalogs of N‐acetyl‐ and N‐benzoyl‐azacyclohex‐2‐enes having an oxygen atom, a methylene‐d2 group or a carbonyl group in place of the C‐4 methylene group have been synthesized. The amide rotational barriers in these compounds have been measured by the total line‐shape analysis of variable‐temperature 1H NMR spectra. The free energies of activation for both the N‐acetyl and N‐benzoyl series decrease in the sequence O≃CD2 > CO. The barriers for the first two compounds in each series are similar to those of the corresponding saturated analogs, a result which confirms recent reports that the long accepted barrier‐decreasing effect of an α‐olefinic substituent on nitrogen is counteracted. Evidence is presented that resonance stabilization of the rotational transition state in the unsaturated compounds still obtains. It is suggested that the introduction of an α‐olefinic substituent on nitrogen has a negligible effect on the amide rotational barriers in the cases of the oxygen and methylene‐d2 analogs, since any increase in the stabilization of the transition state by resonance is offset by the accompanying decrease in the sp3 character of the nitrogen atom. In cases in which a substituent on the olefinic group can interact directly with the lone pair on nitrogen, for example in the carbonyl analogs, then the resonance stabilization of the transition state is dominant.

  DOI：

  10.1002/mrc.1270221103
• 作为产物：
  描述：

  N-乙酰基-4-哌啶酮 、 对甲苯磺酰肼 以 乙醇 为溶剂， 反应 12.0h， 以81%的产率得到N-acetylazacyclohexan-4-one tosylhydrazone
  参考文献：
  名称：

  Effects of substitution on nitrogen on barriers to rotation of amides. 2—Evaluation of the importance of resonance effects

  摘要：

  AbstractAnalogs of N‐acetyl‐ and N‐benzoyl‐azacyclohex‐2‐enes having an oxygen atom, a methylene‐d2 group or a carbonyl group in place of the C‐4 methylene group have been synthesized. The amide rotational barriers in these compounds have been measured by the total line‐shape analysis of variable‐temperature 1H NMR spectra. The free energies of activation for both the N‐acetyl and N‐benzoyl series decrease in the sequence O≃CD2 > CO. The barriers for the first two compounds in each series are similar to those of the corresponding saturated analogs, a result which confirms recent reports that the long accepted barrier‐decreasing effect of an α‐olefinic substituent on nitrogen is counteracted. Evidence is presented that resonance stabilization of the rotational transition state in the unsaturated compounds still obtains. It is suggested that the introduction of an α‐olefinic substituent on nitrogen has a negligible effect on the amide rotational barriers in the cases of the oxygen and methylene‐d2 analogs, since any increase in the stabilization of the transition state by resonance is offset by the accompanying decrease in the sp3 character of the nitrogen atom. In cases in which a substituent on the olefinic group can interact directly with the lone pair on nitrogen, for example in the carbonyl analogs, then the resonance stabilization of the transition state is dominant.

  DOI：

  10.1002/mrc.1270221103

文献信息

• [EN] SUBSTITUTED QUINOXALINE DERIVATIVES<br/>[FR] DÉRIVÉS DE QUINOXALINE SUBSTITUÉS
  申请人：SELVITA S A

  公开号：WO2016180536A1

  公开（公告）日：2016-11-17

  The present invention relates to substituted quinoxaline derivatives. These compounds are useful for the prevention and/or treatment of several medical conditions including hyperproliferative disorders and diseases.

  本发明涉及取代喹喔啉衍生物。这些化合物对预防和/或治疗包括过度增殖性疾病在内的多种医疗状况具有用处。
• SUBSTITUTED QUINOXALINE DERIVATIVES
  申请人：SELVITA S.A.

  公开号：EP3294729A1

  公开（公告）日：2018-03-21