3-(5-Isopropyl-1,3,4-oxadiazol-2-yl)propanoic acid | 1019111-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(5-Isopropyl-1,3,4-oxadiazol-2-yl)propanoic acid
• 英文别名: 3-(5-propan-2-yl-1,3,4-oxadiazol-2-yl)propanoic acid
• CAS: 1019111-17-1
• 化学式: C₈H₁₂N₂O₃
• mdl: MFCD09880433
• 分子量: 184.195
• InChiKey: LQMHXBLLXPHUOL-UHFFFAOYSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  351.9±44.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为产物：
  描述：

  4-[2-(2-Methylpropanoyl)hydrazinyl]-4-oxobutanoic acid 在 四磷十氧化物 、 硫酸 作用下， 以73%的产率得到3-(5-Isopropyl-1,3,4-oxadiazol-2-yl)propanoic acid
  参考文献：
  名称：

  1,3,4-Oxadiazoles for Crystal Engineering. Convenient Synthesis and Self-Assembly: Nonchiral Chains versus Chiral Helices

  摘要：

  A series of new 1,3,4-oxadiazoles containing carboxylic and halogen groups and a double bond have been synthesized in good yields and a multigram scale. This was achieved at room temperature from readily available 1,2-diacylhydrazines using a cheap condensation reagent (the solution of P2O5 in H2SO4). Single-crystal X-ray diffraction analysis has shown that all studied 1,3,4-oxadiazole-containing acids are self-assembled by intermolecular H-bonds into supramolecular zigzag chains or helices, depending on the tecton molecular structure and the type of H-bonding. Factors affecting helix formation have been found, and a Cambridge Structural Database (CSD) survey has been performed to support these findings. Moreover, it has been demonstrated that the tuning of the crystal structure leading to spontaneous symmetry breaking for supramolecular helices based on nonchiral molecules is possible even by as little change in molecular structure as a shift from an isopropyl substituent to a cyclopropyl. Subsequently, the studied 1,3,4-oxadiazole-containing acids and related compounds are found to be easily accessible building blocks for crystal engineering of new chiral materials with tunable supramolecular arrangement.

  DOI：

  10.1021/cg400649h

文献信息

• 1,3,4-Oxadiazoles for Crystal Engineering. Convenient Synthesis and Self-Assembly: Nonchiral Chains versus Chiral Helices
  作者：Oleksii V. Gutov

  DOI：10.1021/cg400649h

  日期：2013.9.4

  A series of new 1,3,4-oxadiazoles containing carboxylic and halogen groups and a double bond have been synthesized in good yields and a multigram scale. This was achieved at room temperature from readily available 1,2-diacylhydrazines using a cheap condensation reagent (the solution of P2O5 in H2SO4). Single-crystal X-ray diffraction analysis has shown that all studied 1,3,4-oxadiazole-containing acids are self-assembled by intermolecular H-bonds into supramolecular zigzag chains or helices, depending on the tecton molecular structure and the type of H-bonding. Factors affecting helix formation have been found, and a Cambridge Structural Database (CSD) survey has been performed to support these findings. Moreover, it has been demonstrated that the tuning of the crystal structure leading to spontaneous symmetry breaking for supramolecular helices based on nonchiral molecules is possible even by as little change in molecular structure as a shift from an isopropyl substituent to a cyclopropyl. Subsequently, the studied 1,3,4-oxadiazole-containing acids and related compounds are found to be easily accessible building blocks for crystal engineering of new chiral materials with tunable supramolecular arrangement.