N,N-diisopropyl-4-fluoro-2-(hydroxymethyl)benzamide | 1225544-94-4

• 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,N-diisopropyl-4-fluoro-2-(hydroxymethyl)benzamide
• 英文别名: 4-fluoro-2-(hydroxymethyl)-N,N-di(propan-2-yl)benzamide
• CAS: 1225544-94-4
• 化学式: C₁₄H₂₀FNO₂
• 分子量: 253.317
• InChiKey: DEVLRWVGIFGAIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C(Solv: hexane (110-54-3))
• 沸点：
  400.1±40.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N,N-diisopropyl-4-fluoro-2-(hydroxymethyl)benzamide 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以86%的产率得到5-氟-1(3H)-异苯并呋喃酮
  参考文献：
  名称：

  Manufacturing Synthesis of 5-Substituted Phthalides

  摘要：

  A manufacturing synthesis of 5-chlorophthalide has been elaborated. The key step of the procedure is ortho-lithiation of 4-chloro-N,N-diisopropylbenzamide, followed by formylation with dimethyl formamide. Reduction of the formyl moiety and subsequent ring closure, which can be carried out also in one pot, led to 5-chlorophthalide in high overall yield. The procedure has also been successfully adapted for the synthesis of the 5-fluoro and 5-trifluoromethyl analogues. The compounds thus obtained are useful building blocks in the synthesis of various heterocyclic ring systems.

  DOI：

  10.1021/op100049t
• 作为产物：
  描述：

  4-fluoro-N,N-diisopropylbenzamide 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 6.0h， 生成 N,N-diisopropyl-4-fluoro-2-(hydroxymethyl)benzamide
  参考文献：
  名称：

  Manufacturing Synthesis of 5-Substituted Phthalides

  摘要：

  A manufacturing synthesis of 5-chlorophthalide has been elaborated. The key step of the procedure is ortho-lithiation of 4-chloro-N,N-diisopropylbenzamide, followed by formylation with dimethyl formamide. Reduction of the formyl moiety and subsequent ring closure, which can be carried out also in one pot, led to 5-chlorophthalide in high overall yield. The procedure has also been successfully adapted for the synthesis of the 5-fluoro and 5-trifluoromethyl analogues. The compounds thus obtained are useful building blocks in the synthesis of various heterocyclic ring systems.

  DOI：

  10.1021/op100049t