2,2-Dimethyl-5-nonanoyl-1,3-dioxane-4,6-dione | 230975-81-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-5-nonanoyl-1,3-dioxane-4,6-dione
• CAS: 230975-81-2
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: CYHQSJZGYALRLG-UHFFFAOYSA-N

物化性质

• 沸点：
  468.1±45.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-5-nonanoyl-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 16.0h， 生成 4-hydroxy-6-octyl-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
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 壬酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 2,2-Dimethyl-5-nonanoyl-1,3-dioxane-4,6-dione
  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

• OIKAWA YUJI; SUGANO KIYOSHI; YONEMITSU OSAMU, J. ORG. CHEM., 1978, 43, NO 10, 2087-2088
  作者：OIKAWA YUJI、 SUGANO KIYOSHI、 YONEMITSU OSAMU

  DOI：——

  日期：——
• 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.