N-(3-cyano-2-hydroxy-propyl)-benzamide | 91350-64-0

• 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-(3-cyano-2-hydroxy-propyl)-benzamide
• 英文别名: N-(3-Cyan-2-hydroxy-propyl)-benzamid；N-(β-Oxy-γ-cyan-propyl)-benzamid；γ-Benzamino-β-oxy-butyronitril；3-Benzamido-1-cyan-2-hydroxy-propan；N-(3-cyano-2-hydroxypropyl)benzamide
• CAS: 91350-64-0
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: HUWKXUIVXXMPDB-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C
• 沸点：
  529.9±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-cyano-2-hydroxy-propyl)-benzamide 在 盐酸 作用下， 生成 rac-4-benzoylamino-3-hydroxybutyric acid
  参考文献：
  名称：

  Bergmann; Brand; Weinmann, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1923, vol. 131, p. 12

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 在 吡啶 、 ammonium hydroxide 、 potassium iodide 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 生成 N-(3-cyano-2-hydroxy-propyl)-benzamide
  参考文献：
  名称：

  4-Benzoylamino-3-hydroxybutyric Acid, Historically First “Anomalous Racemate”: Reinvestigation

  摘要：

  Chiral 4-benzoylamino-3-hydroxybutyric acid (1) was recognized in 1930 as the first example of anomalous racemates (correct to say, anomalous conglomerates), that is, specific addition compounds formed by different enantiomers in unequal ratio. Through the comparative (racemic against homochiral samples) inspection of the IR spectra, single crystal X-ray diffraction, PXRD analysis, and solubility data we have found that this substance forms normal racemic compound in the solid state, and must be excluded from the very short list of anomalous conglomerates. At the same time homo-1 is dissolved in 25 times better than rac-1, and this feature belongs to another interesting and rare type, namely, anticonglomerates. Some of the reasons for this behavior are discussed.

  DOI：

  10.1021/cg5017615

文献信息

• Notes - Improved Synthesis of DL-Carnitine Hydrochloride
  作者：Franco Mazzetti、Richard Lemmon

  DOI：10.1021/jo01353a606

  日期：1957.2
• Bergmann; Brand; Weinmann, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1923, vol. 131, p. 12
  作者：Bergmann、Brand、Weinmann

  DOI：——

  日期：——
• DE409345
  申请人：——

  公开号：——

  公开（公告）日：——
• 4-Benzoylamino-3-hydroxybutyric Acid, Historically First “Anomalous Racemate”: Reinvestigation
  作者：Alexander A. Bredikhin、Zemfira A. Bredikhina、Dmitry V. Zakharychev、Aida I. Samigullina、Aidar T. Gubaidullin

  DOI：10.1021/cg5017615

  日期：2015.3.4

  Chiral 4-benzoylamino-3-hydroxybutyric acid (1) was recognized in 1930 as the first example of anomalous racemates (correct to say, anomalous conglomerates), that is, specific addition compounds formed by different enantiomers in unequal ratio. Through the comparative (racemic against homochiral samples) inspection of the IR spectra, single crystal X-ray diffraction, PXRD analysis, and solubility data we have found that this substance forms normal racemic compound in the solid state, and must be excluded from the very short list of anomalous conglomerates. At the same time homo-1 is dissolved in 25 times better than rac-1, and this feature belongs to another interesting and rare type, namely, anticonglomerates. Some of the reasons for this behavior are discussed.