1-(acetoxymethyl)-isoquinoline | 27039-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(acetoxymethyl)-isoquinoline
• 英文别名: Isoquinolin-1-ylmethyl acetate
• CAS: 27039-28-7
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: ZRJPPCGHOYVXBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(acetoxymethyl)-isoquinoline 、 3-戊酮 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到1-(2-ethyl-2-hydroxybutyl)-isoquinoline
  参考文献：
  名称：

  Samarium-Promoted Coupling of Pyridine-Based Heteroaryl Analogues of Benzylic Acetates with Carbonyl Compounds

  摘要：

  [GRAPHICS]2-Substituted pyridine, quinoline, isoquinoline, bipyridine, and 1,10-phenanthroline analogues of benzylic acetates undergo Sml(2)-promoted coupling with aldehydes and ketones to afford (2-hydroxyalkyl)heteroaromatics.

  DOI：

  10.1021/ol050944z
• 作为产物：
  描述：

  异喹啉羧酸 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 硫酸 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 51.0h， 生成 1-(acetoxymethyl)-isoquinoline
  参考文献：
  名称：

  Samarium-Promoted Coupling of Pyridine-Based Heteroaryl Analogues of Benzylic Acetates with Carbonyl Compounds

  摘要：

  [GRAPHICS]2-Substituted pyridine, quinoline, isoquinoline, bipyridine, and 1,10-phenanthroline analogues of benzylic acetates undergo Sml(2)-promoted coupling with aldehydes and ketones to afford (2-hydroxyalkyl)heteroaromatics.

  DOI：

  10.1021/ol050944z

文献信息

• Hydroxymethylation of Quinolines with Na₂ S₂ O₈ by a Radical Pathway
  作者：Luan Zhou、Naoki Okugawa、Hideo Togo

  DOI：10.1002/ejoc.201701321

  日期：2017.11.9

  Treatment of quinolines bearing methyl, fluoro, chloro, bromo, acetyl, methoxycarbonyl, trifluoromethyl, or cyano groups with Na2S2O8 in a mixture of methanol and water at 70 °C for 4 h gave the corresponding hydroxymethylated compounds in good to moderate yields. The hydroxymethyl group of the product was transformed into aldehyde, ester, amide, aminomethyl, cyano, and tetrazole groups.

  在甲醇和水的混合物中，用Na 2 S 2 O 8在70°C下处理带有甲基，氟，氯，溴，乙酰基，甲氧基羰基，三氟甲基或氰基的喹啉4小时，得到相应的羟甲基化化合物中等产量。产物的羟甲基被转化为醛，酯，酰胺，氨甲基，氰基和四唑基。
• FUNGAL CELL WALL SYNTHESIS GENE
  申请人：Tsukahara Kappei

  公开号：US20080261272A1

  公开（公告）日：2008-10-23

  A reporter system reflecting the transport process that transports GPI-anchored proteins to the cell wall was constructed and compounds inhibiting this process were discovered. Further, genes conferring resistance to the above compounds were identified and methods of screening for compounds that inhibit the activity of the proteins encoded by these genes were developed. Therefore, through the novel compounds, the present invention showed that antifungal agents having a novel mechanism, i.e. inhibiting the process that transports GPI-anchored proteins to the cell wall, could be achieved.

  建立了一个反映将GPI锚定蛋白转运到细胞壁的运输过程的记者系统，并发现了抑制该过程的化合物。此外，还鉴定了赋予抵抗上述化合物的基因，并开发了筛选抑制这些基因编码蛋白活性的化合物的方法。因此，通过这些新型化合物，本发明展示了可以实现具有新型机制的抗真菌剂，即抑制将GPI锚定蛋白转运到细胞壁的过程。