phthoxazolin A | 135415-76-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: phthoxazolin A
• 英文别名: (4Z,6Z,8E)-3-hydroxy-2,2,4-trimethyl-10-(1,3-oxazol-5-yl)deca-4,6,8-trienamide
• CAS: 135415-76-8
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: MRTUFVRJHFZVOT-XSOJHLTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• Highly Stereoselective Palladium Catalysed Cross-Coupling Approaches to the Total Synthesis of Phthoxazolin A
  作者：Nadine Hénaff、Andrew Whiting

  DOI：10.1016/s0040-4020(00)00182-4

  日期：2000.7

  The first total synthesis of racemic Phthoxazolin A 4 is described, involving a convergent series of palladium cross-coupling reactions to stereoselectively construct the Z,Z,E-trienyl unit. The most important steps involve using vinylboronate pinacol ester 1 as a vinyl dianion equivalent, by employing a Heck coupling of a vinyl iodide 9 with the vinyl boronate 1, followed by a deboronation–iodination

  描述了外消旋邻苯二恶唑啉A 4的第一个全合成，涉及一系列收敛的钯交叉偶联反应，以立体选择性地构建Z，Z，E-三烯基单元。最重要的步骤包括使用乙烯基碘化物9与乙烯基硼酸酯1进行Heck偶联，将乙烯基硼酸酯频哪醇酯1用作乙烯基二价阴离子，然后进行脱硼-碘化顺序以及烯烃立体化学的反转，以提供新的烯基碘化物6。乙烯基碘化物6与恶唑基烯基锡烷40的最终Stille偶联提供了甲唑啉A 4。
• A Convergent Stereoselective Total Synthesis of Racemic Phthoxazolin A
  作者：Nadine Hénaff、Andrew Whiting

  DOI：10.1021/ol990967b

  日期：1999.10.1

  [GRAPHICS]The first total synthesis of phthoxazolin A is reported which involves a convergent series of palladium-catalyzed cross coupling reactions to stereoselectively construct the Z,Z,E-trienyl unit of phthoxazolin A. The most important steps of the synthesis involve using vinylboronate pinacol ester as a vinyl dianion equivalent, by employing a Heck coupling of a vinyl iodide with the vinylboronate, followed by a deboronation-iodination sequence with inversion of alkene stereochemistry and Stille coupling of the resulting vinyl iodide.
• 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.