4Z,6Z,8E-3-acetoxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrieneamide | 135354-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4Z,6Z,8E-3-acetoxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrieneamide
• 英文别名: [(4Z,6Z,8E)-1-amino-2,2,4-trimethyl-10-(1,3-oxazol-5-yl)-1-oxodeca-4,6,8-trien-3-yl] acetate
• CAS: 135354-13-1
• 化学式: C₁₈H₂₄N₂O₄
• 分子量: 332.4
• InChiKey: ZZDVXZUHHYCWJU-CWLWAJQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4Z,6Z,8E-3-acetoxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrieneamide 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 以92%的产率得到phthoxazolin A
  参考文献：
  名称：

  The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach

  摘要：

  The Stille coupling between a common oxazole vinyl iodide and stereodefined stannyl-diene units is described as the cornerstone of a unified synthetic route to the inthomycin family of bioactive Streptomyces metabolites. This procedure has been utilised to prepare (+)-inthomycin B and (+)-inthomycin C for the first time; in these examples the stereogenic centre was introduced using the Kiyooka ketene acetal/amino acid-derived oxazaborolidinone variant of the Mukaiyama aldol reaction. In addition, a convenient preparation of rac-inthomycin A is described based on the same strategy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.116
• 作为产物：
  描述：

  (4Z,6Z,8E)-3-acetoxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrienoic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以70%的产率得到4Z,6Z,8E-3-acetoxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrieneamide
  参考文献：
  名称：

  The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach

  摘要：

  The Stille coupling between a common oxazole vinyl iodide and stereodefined stannyl-diene units is described as the cornerstone of a unified synthetic route to the inthomycin family of bioactive Streptomyces metabolites. This procedure has been utilised to prepare (+)-inthomycin B and (+)-inthomycin C for the first time; in these examples the stereogenic centre was introduced using the Kiyooka ketene acetal/amino acid-derived oxazaborolidinone variant of the Mukaiyama aldol reaction. In addition, a convenient preparation of rac-inthomycin A is described based on the same strategy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.116