methyl (4Z,6Z,8E)-3-hydroxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrienoate | 1035538-78-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (4Z,6Z,8E)-3-hydroxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrienoate
• 英文别名: methyl (4Z,6Z,8E)-3-hydroxy-2,2,4-trimethyl-10-(1,3-oxazol-5-yl)deca-4,6,8-trienoate
• CAS: 1035538-78-3
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: NWDTXLYPSKCNJG-CWLWAJQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (4Z,6Z,8E)-3-hydroxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrienoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.5h， 以92%的产率得到4Z,6Z,8E-3-hydroxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrienoic acid
  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：

  5-[(E)-3-iodo-2-propenyl]oxazole 、 methyl 4Z,6Z-3-hydroxy-2,2,4-trimethyl-7-(tributylstannyl)-4,6-heptadienoate 在 Pd(CH₃CN)Cl₂ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以77%的产率得到methyl (4Z,6Z,8E)-3-hydroxy-2,2,4-trimethyl-10-(oxazol-5-yl)-4,6,8-decatrienoate
  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

文献信息

• The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach
  作者：Michael R. Webb、Matthew S. Addie、Catherine M. Crawforth、James W. Dale、Xavier Franci、Mathieu Pizzonero、Craig Donald、Richard J.K. Taylor

  DOI：10.1016/j.tet.2008.01.116

  日期：2008.5

  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.