(2E,6Z)-methyl 7-iodohepta-2,6-dienoate | 950697-10-6

• 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: (2E,6Z)-methyl 7-iodohepta-2,6-dienoate
• 英文别名: methyl (2E,6Z)-7-iodohepta-2,6-dienoate
• CAS: 950697-10-6
• 化学式: C₈H₁₁IO₂
• 分子量: 266.079
• InChiKey: VLJYJMSEIFQRQH-GUBXDBFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,6Z)-methyl 7-iodohepta-2,6-dienoate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 二异丁基氢化铝 、 二甲基氨基丙基乙基碳酰胺 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-N-((2E,6Z)-11-(4-(3-(benzyloxy)propyl)oxazol-2-yl)-12-hydroxydodeca-2,6-dien-8-yn-1-yl)-3-methoxy-N-methylbut-2-enamide
  参考文献：
  名称：

  Synthesis of the C9–C29 fragments of ajudazols A and B

  摘要：

  The syntheses of both C9-C29 fragments 3 and 4 of the myxobacteria metabolites ajudazols A (1) and B (2) are described. The key steps were a cyclodehydration to form the oxazole, Sonogashira coupling to form the C18-C19 bond and a P-2 Ni mediated partial alkyne hydrogenation to install the C17-C18 Z-alkene. The C15 alkene in the ajudazol A fragnient 3 was introduced in the final steps by elimination of the corresponding primary alcohol. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.072
• 作为产物：
  描述：

  (Z)-5-iodo-4-penten-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2E,6Z)-methyl 7-iodohepta-2,6-dienoate
  参考文献：
  名称：

  异苯并呋喃作为合成中间体：8-表-（-）-Ajudazol B的合成和生物活性

  摘要：

  利用异苯并呋喃作为合成中间体，实现了8- Epi -（-）-ajudazol B的分步经济收敛全合成。这种方法证明了异苯并呋喃作为反应性中间体的合成用途，并提供了一种快速有效的方法，可通过最少的操作来生成具有抗真菌活性的阿杜唑类似物。

  DOI：

  10.1002/ejoc.202001216

文献信息

• Total Synthesis of the Proposed Structure of 8-Deshydroxyajudazol A: A Modified Approach to 2,4-Disubstituted Oxazoles
  作者：Stephen Birkett、Danny Ganame、Bill C. Hawkins、Sébastien Meiries、Tim Quach、Mark A. Rizzacasa

  DOI：10.1021/jo302055w

  日期：2013.1.4

  The total synthesis of the proposed structure for the minor Myxobacterial metabolite 8-deshydroxyajudazol A (3) is described. The isochromanone moiety present in the eastern fragment was constructed by an intramolecular-Diels-Alder (IMDA). Difficulties were encountered with the formation of the 2,4-disubstituted oxazole, so this was synthesized via a modified approach. This involved selective acylation of the diol 7 with acid 8, azide displacement of the secondary alcohol, and subsequent azide reduction in the presence of base which induced an O,N shift to give the hydroxyamide 23. Cyclodehydration then gave the desired oxazole 24 and deprotection followed by mesylation and elimination produced the C15 alkene S. Sonogashira coupling with the eastern fragment vinyl iodide 6 and partial reduction yielded 8-deshydroxyajudazol A (3).