7-methoxy-3-octylisobenzofuran-1(3H)-one | 1395236-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 7-methoxy-3-octylisobenzofuran-1(3H)-one
• 英文别名: 7-methoxy-3-octyl-3H-2-benzofuran-1-one
• CAS: 1395236-46-0
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: RCNGILBUGSXCRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-octylisobenzofuran-1(3H)-one 在 magnesium iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以66%的产率得到7-hydroxy-3-octylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  外消旋paecilocin A及其衍生物对耐甲氧西林的金黄色葡萄球菌的合成及抑菌作用

  摘要：

  据报道，在四个步骤中，外消旋paecilocin A（一种天然海洋邻苯二甲酸酯）的总合成。合成途径包括碘-镁交换，然后在醛上缩合，代表了足够灵活的方法以允许合成十二个类似物。研究了合成的化合物对甲氧西林敏感的金黄色葡萄球菌（MSSA）和耐甲氧西林的菌株（MRSA）的抗菌活性。发现三种类似物与天然化合物相比对MRSA具有相似或更好的抗菌活性。

  DOI：

  10.1016/j.tetlet.2021.152888
• 作为产物：
  描述：

  正辛基镁溴盐 在 silver(l) oxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 14.75h， 生成 7-methoxy-3-octylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Design and synthesis of marine fungal phthalide derivatives as PPAR-γ agonists

  摘要：

  On the basis of a marine fungal phthalide (paecilocin A) skeleton, we synthesized 20 analogs and evaluated them for peroxisome proliferator-activated receptor gamma (PPAR-gamma) binding and activation. Among these analogs, 6 and 7 had significant PPAR-c binding activity, and 7 showed further PPAR-gamma activation in rat liver Ac2F cells. In docking simulation, 7 formed H bonds with key amino acid residues of the PPAR-gamma binding domain, and the overall positioning was similar to rosiglitazone. This new phthalide derivative is considered an interesting new molecular class of PPAR-gamma ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.039

文献信息

• Synthesis and antibacterial activity of racemic paecilocin A and its derivatives against methicillin-sensitive and -resistant Staphylococcus aureus
  作者：Walaa Ibraheem、Quentin Wils、Emilie Camiade、Elhadi Ahmed、Jérôme Thibonnet、Emilie Thiery、Julien Petrignet

  DOI：10.1016/j.tetlet.2021.152888

  日期：2021.3

  A total synthesis in four steps of racemic paecilocin A, a natural marine phthalide is reported. The synthetic pathway includes an iodine-magnesium exchange followed by a condensation on an aldehyde and represents a sufficiently flexible approach to allow the synthesis of twelve analogs. The synthesized compounds were investigated for their antibacterial activity against methicillin-sensitive Staphylococcus

  据报道，在四个步骤中，外消旋paecilocin A（一种天然海洋邻苯二甲酸酯）的总合成。合成途径包括碘-镁交换，然后在醛上缩合，代表了足够灵活的方法以允许合成十二个类似物。研究了合成的化合物对甲氧西林敏感的金黄色葡萄球菌（MSSA）和耐甲氧西林的菌株（MRSA）的抗菌活性。发现三种类似物与天然化合物相比对MRSA具有相似或更好的抗菌活性。
• Design and synthesis of marine fungal phthalide derivatives as PPAR-γ agonists
  作者：Bin Xiao、Jun Yin、Minhi Park、Juan Liu、Jian Lin Li、Eun La Kim、Jongki Hong、Hae Young Chung、Jee H. Jung

  DOI：10.1016/j.bmc.2012.06.039

  日期：2012.8

  On the basis of a marine fungal phthalide (paecilocin A) skeleton, we synthesized 20 analogs and evaluated them for peroxisome proliferator-activated receptor gamma (PPAR-gamma) binding and activation. Among these analogs, 6 and 7 had significant PPAR-c binding activity, and 7 showed further PPAR-gamma activation in rat liver Ac2F cells. In docking simulation, 7 formed H bonds with key amino acid residues of the PPAR-gamma binding domain, and the overall positioning was similar to rosiglitazone. This new phthalide derivative is considered an interesting new molecular class of PPAR-gamma ligands. (C) 2012 Elsevier Ltd. All rights reserved.