3-pentadecylisocoumarin | 106180-95-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-pentadecylisocoumarin
• 英文别名: 3-Pentadecyl-1H-2-benzopyran-1-one；3-pentadecylisochromen-1-one
• CAS: 106180-95-4
• 化学式: C₂₄H₃₆O₂
• 分子量: 356.549
• InChiKey: UFXOWKKFMKQYOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  3-pentadecylisocoumarin 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以75%的产率得到2-(2-oxoheptadecyl)benzoic acid
  参考文献：
  名称：

  A Short Total Synthesis of rac -Peniolactol

  摘要：

  A short facile synthesis of the fungal metabolite (+/-)-3,4-dihydro-3,6,8-trihydroxy-3-pentadecylisocoumarin (peniolactol) has been achieved. Condensation of hexadecanoyl chloride with 3,5-dimethoxyhomophthalic acid afforded 6,8-dimethoxy-3-pentadecylisocoumarin, which on sequential saponification and demethylation furnished rac-peniolactol in 31% overall yield. The ring-chain tautomerism was studied in solution by H-1 NMR and the mass fragmentation pattern. 3-Pentadecylisocoumarin was also synthesized and saponified to the corresponding keto acid as a model compound for comparative studies.

  DOI：

  10.1007/s00706-002-0515-6
• 作为产物：
  描述：

  邻羧基苯乙酸 、 棕榈酰氯 以82%的产率得到3-pentadecylisocoumarin
  参考文献：
  名称：

  A Short Total Synthesis of rac -Peniolactol

  摘要：

  A short facile synthesis of the fungal metabolite (+/-)-3,4-dihydro-3,6,8-trihydroxy-3-pentadecylisocoumarin (peniolactol) has been achieved. Condensation of hexadecanoyl chloride with 3,5-dimethoxyhomophthalic acid afforded 6,8-dimethoxy-3-pentadecylisocoumarin, which on sequential saponification and demethylation furnished rac-peniolactol in 31% overall yield. The ring-chain tautomerism was studied in solution by H-1 NMR and the mass fragmentation pattern. 3-Pentadecylisocoumarin was also synthesized and saponified to the corresponding keto acid as a model compound for comparative studies.

  DOI：

  10.1007/s00706-002-0515-6

文献信息

• Synthesis of some 3-aryl-1<i>H</i>-isochromene-1-thiones
  作者：Aamer Saeed、Zaman Ashraf

  DOI：10.1002/jhet.5570450307

  日期：2008.5

  A rapid microwave-accelerated thionation of some 3-substitued isocoumarins to corresponding 1-thio-isocoumarins was achieved employing Lawesson's reagent under solventless conditions.

  使用Lawesson试剂在无溶剂条件下，实现了一些3取代的异香豆素对相应的1硫代异香豆素的快速微波加速硫化。
• Efficient synthesis of some 3-arylisoquinolin-1(2H)-ones
  作者：Aamer Saeed、Zaman Ashraf

  DOI：10.1007/s10593-008-0140-3

  日期：2008.8

  A number of 3-arylisoquinolin-1(2H)-ones were efficiently prepared from the corresponding 3-arylisocoumarins by refluxing with methanamide.
• KAJI H.; YAMADA M.; NOZAWA K.; KAWAI K.; NAKAJIMA S., ORG. PREP. AND PROCED. INT., 18,(1986) N 4, 253-262
  作者：KAJI H.、 YAMADA M.、 NOZAWA K.、 KAWAI K.、 NAKAJIMA S.

  DOI：——

  日期：——
• A Short Total Synthesis of rac -Peniolactol
  作者：Aamer Saeed

  DOI：10.1007/s00706-002-0515-6

  日期：2003.2.1

  A short facile synthesis of the fungal metabolite (+/-)-3,4-dihydro-3,6,8-trihydroxy-3-pentadecylisocoumarin (peniolactol) has been achieved. Condensation of hexadecanoyl chloride with 3,5-dimethoxyhomophthalic acid afforded 6,8-dimethoxy-3-pentadecylisocoumarin, which on sequential saponification and demethylation furnished rac-peniolactol in 31% overall yield. The ring-chain tautomerism was studied in solution by H-1 NMR and the mass fragmentation pattern. 3-Pentadecylisocoumarin was also synthesized and saponified to the corresponding keto acid as a model compound for comparative studies.