1-iodohepta-1,5-dien-7-ol | 1412889-79-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1-iodohepta-1,5-dien-7-ol
• 英文别名: (2E,6Z)-7-iodohepta-2,6-dien-1-ol
• CAS: 1412889-79-2
• 化学式: C₇H₁₁IO
• 分子量: 238.068
• InChiKey: VRGZHGHNICJHMR-UZNMPDEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-iodohepta-1,5-dien-7-ol 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 四溴化碳 、 1-羟基苯并三唑 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 46.5h， 生成 (E)-N-[(2E,6Z)-11-[4-[(2S)-2-[(3R)-8-hydroxy-7-methyl-1-oxo-3,4-dihydroisochromen-3-yl]propyl]-1,3-oxazol-2-yl]dodeca-2,6,11-trien-8-ynyl]-3-methoxy-N-methylbut-2-enamide
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of 8-Deshydroxyajudazol A: A Modified Approach to 2,4-Disubstituted Oxazoles

  摘要：

  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).

  DOI：

  10.1021/jo302055w
• 作为产物：
  描述：

  (Z)-6-iodo-5-hexenal 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 1-iodohepta-1,5-dien-7-ol
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of 8-Deshydroxyajudazol A: A Modified Approach to 2,4-Disubstituted Oxazoles

  摘要：

  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).

  DOI：

  10.1021/jo302055w

文献信息

• Isobenzofurans as Synthetic Intermediates: Synthesis and Biological Activity of 8‐ <i>epi</i> ‐(–)‐Ajudazol B
  作者：Liam Adair、Ben A. Egan、Colin M. Pearson、Ricardo Lopez‐Gonzalez、Michal Kuchar、Artemio Mendoza‐Mendoza、Joëlle Prunet、Rodolfo Marquez

  DOI：10.1002/ejoc.202001216

  日期：2020.11.15

  The step‐economic convergent total synthesis of 8‐epi‐(–)‐ajudazol B has been achieved taking advantage of isobenzofuran as synthetic intermediates. This approach proves the synthetic utility of isobenzofurans as reactive intermediates and provides a fast and efficient way to generate ajudazol analogues with anti‐fungal activity through minimal manipulation.

  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。