6-(1-benzoylpentyl)-2,2-dimethyl-4H-1,3-dioxin-4-one | 857249-01-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(1-benzoylpentyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
• 英文别名: 2,2-Dimethyl-6-(1-oxo-1-phenylhexan-2-yl)-1,3-dioxin-4-one
• CAS: 857249-01-5
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: MWDDEFLIYNMNHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(1-benzoylpentyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 以 甲苯 为溶剂， 反应 0.5h， 以26%的产率得到5-butyl-4-hydroxy-6-phenyl-2H-pyran-2-one
  参考文献：
  名称：

  Facile Syntheses of 2,2-Dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the Corresponding 6-Substituted 4-Hydroxy-2-pyrones

  摘要：

  A variety of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones 5a-l and the corresponding 6-substituted 4-hydroxy-2-pyrones 3a-l were prepared in high yields under mild reaction conditions by the reaction of 2,2,6-trimethyl-1,3-dioxin-4-one 4 with 1-acylbenzotriazoles 9 in the presence of LDA followed by thermal cyclization of 5a-l to 3a-1. Synthesis of novel 6-(1-benzoylalkyl)-2,2-dimethyl-1,3-dioxin-4-ones 12a-c was achieved by alkylation of dioxinone 5a and their subsequent cyclization gave 5-alkyl-4-hydroxy-2-pyrones 13a-c.

  DOI：

  10.1021/jo050307m
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 362.42h， 生成 6-(1-benzoylpentyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Facile Syntheses of 2,2-Dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the Corresponding 6-Substituted 4-Hydroxy-2-pyrones

  摘要：

  A variety of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones 5a-l and the corresponding 6-substituted 4-hydroxy-2-pyrones 3a-l were prepared in high yields under mild reaction conditions by the reaction of 2,2,6-trimethyl-1,3-dioxin-4-one 4 with 1-acylbenzotriazoles 9 in the presence of LDA followed by thermal cyclization of 5a-l to 3a-1. Synthesis of novel 6-(1-benzoylalkyl)-2,2-dimethyl-1,3-dioxin-4-ones 12a-c was achieved by alkylation of dioxinone 5a and their subsequent cyclization gave 5-alkyl-4-hydroxy-2-pyrones 13a-c.

  DOI：

  10.1021/jo050307m

文献信息

• Facile Syntheses of 2,2-Dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the Corresponding 6-Substituted 4-Hydroxy-2-pyrones
  作者：Alan R. Katritzky、Zuoquan Wang、Mingyi Wang、C. Dennis Hall、Kazuyuki Suzuki

  DOI：10.1021/jo050307m

  日期：2005.6.1

  A variety of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones 5a-l and the corresponding 6-substituted 4-hydroxy-2-pyrones 3a-l were prepared in high yields under mild reaction conditions by the reaction of 2,2,6-trimethyl-1,3-dioxin-4-one 4 with 1-acylbenzotriazoles 9 in the presence of LDA followed by thermal cyclization of 5a-l to 3a-1. Synthesis of novel 6-(1-benzoylalkyl)-2,2-dimethyl-1,3-dioxin-4-ones 12a-c was achieved by alkylation of dioxinone 5a and their subsequent cyclization gave 5-alkyl-4-hydroxy-2-pyrones 13a-c.