N'-(2H-pyran-3(4H,5H,6H)-ylidene)benzohydrazide | 873542-04-2

• 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'-(2H-pyran-3(4H,5H,6H)-ylidene)benzohydrazide
• 英文别名: Benzoic acid, 2-(dihydro-2H-pyran-3(4H)-ylidene)hydrazide；N-(oxan-3-ylideneamino)benzamide
• CAS: 873542-04-2
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: HTWCAUYUWAOFMA-UHFFFAOYSA-N

物化性质

• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-(2H-pyran-3(4H,5H,6H)-ylidene)benzohydrazide 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 氢气 、 (+)-1,2-双((2S,5S)-2,5-二乙基磷)苯 作用下， 以 甲醇 为溶剂， 30.0 ℃ 、2.07 MPa 条件下， 反应 20.0h， 生成 N'-[(3R)-oxan-3-yl]benzohydrazide 、 (S)-N'-(tetrahydro-2H-pyran-3-yl)benzohydrazide
  参考文献：
  名称：

  Catalytic asymmetric hydrogenation of heterocyclic ketone-derived hydrazones, pronounced solvent effect on the inversion of configuration

  摘要：

  An enantioselective hydrogenation of hydrazones derived from heterocyclic ketones was developed with up to 85% ee. The enantiomeric purity was enriched to >99% ee by crystallization from EtOAc in >80% yield. Optimization studies have revealed a notable solvent effect that resulted in inversion of enantioselectivity from 85% ee in MeOH to -27% ee in DCE. The hydrazone geometry and possible hydrogenation via endocyclic alkene were examined as possible factors for the inversion of enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.017
• 作为产物：
  描述：

  四氢-2H-吡喃-3-酮 、 苯甲酰肼 以 甲醇 为溶剂， 反应 7.0h， 以82%的产率得到N'-(2H-pyran-3(4H,5H,6H)-ylidene)benzohydrazide
  参考文献：
  名称：

  Catalytic asymmetric hydrogenation of heterocyclic ketone-derived hydrazones, pronounced solvent effect on the inversion of configuration

  摘要：

  An enantioselective hydrogenation of hydrazones derived from heterocyclic ketones was developed with up to 85% ee. The enantiomeric purity was enriched to >99% ee by crystallization from EtOAc in >80% yield. Optimization studies have revealed a notable solvent effect that resulted in inversion of enantioselectivity from 85% ee in MeOH to -27% ee in DCE. The hydrazone geometry and possible hydrogenation via endocyclic alkene were examined as possible factors for the inversion of enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.017