3-acetyl-6-sec-butyl-4-hydroxy-2-pyrone | 223435-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-6-sec-butyl-4-hydroxy-2-pyrone
• 英文别名: 3-Acetyl-6-butan-2-yl-4-hydroxypyran-2-one
• CAS: 223435-22-1
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: WAPUIWYKGRROOK-UHFFFAOYSA-N

物化性质

• 沸点：
  334.5±42.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetyl-6-sec-butyl-4-hydroxy-2-pyrone 在 三乙基硅烷 、 lithium perchlorate 作用下， 以 三氟乙酸 为溶剂， 反应 4.0h， 以86%的产率得到6-丁烷-2-基-3-乙基-2-羟基吡喃-4-酮
  参考文献：
  名称：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin

  摘要：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl-4-hydroxy-2-pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3-oxoacyl)-2,2-dimethyl-1,3-dioxane-4,6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00150-7
• 作为产物：
  描述：

  2,2-Dimethyl-5-(2-methylbutanoyl)-1,3-dioxane-4,6-dione 在 盐酸 、 4-二甲氨基吡啶 、 sodium methylate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 3-acetyl-6-sec-butyl-4-hydroxy-2-pyrone
  参考文献：
  名称：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin

  摘要：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl-4-hydroxy-2-pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3-oxoacyl)-2,2-dimethyl-1,3-dioxane-4,6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00150-7

文献信息

• A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin
  作者：Igor P. Lokot、Felix S. Pashkovsky、Fedor A. Lakhvich

  DOI：10.1016/s0040-4020(99)00150-7

  日期：1999.4

  A new approach to the synthesis of 3,6- and 5,6-dialkyl-4-hydroxy-2-pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3-oxoacyl)-2,2-dimethyl-1,3-dioxane-4,6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551. (C) 1999 Elsevier Science Ltd. All rights reserved.