4-乙酰氧基甲基吡啶 | 14061-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-乙酰氧基甲基吡啶
• 英文名称: 4-Acetoxy-methyl-pyridin-methiodid
• 英文别名: 4-[(Acetyloxy)methyl]-1-methylpyridin-1-ium iodide；(1-methylpyridin-1-ium-4-yl)methyl acetate;iodide
• CAS: 14061-11-1
• 化学式: C₉H₁₂NO₂*I
• 分子量: 293.104
• InChiKey: KZXKJFBXXNUBKV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.42
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-乙酰氧基甲基吡啶 在 silver perchlorate 作用下， 以 乙腈 为溶剂， 以82%的产率得到N-methyl picolinium acetate perchlorate
  参考文献：
  名称：

  C−O Bond Fragmentation of 4-Picolyl- and N-Methyl-4-picolinium Esters Triggered by Photochemical Electron Transfer

  摘要：

  Photochemical reduction of several 4-picolyl- and N-methyl-4-picolinium esters was examined using product analysis, laser flash photolysis, and fluorescence quenching. It is demonstrated that the radical (anions) formed in these reactions readily fragment to yield a carboxylic acid and a 4-pyridylmethyl radical intermediate. The high chemical and quantum yields observed for these photoreactions suggests that these esters can be used as photolabile protecting groups.

  DOI：

  10.1021/jo049501j
• 作为产物：
  描述：

  4-吡啶甲醇 在 三乙胺 作用下， 以 甲醇 、 苯 为溶剂， 反应 24.0h， 生成 4-乙酰氧基甲基吡啶
  参考文献：
  名称：

  C−O Bond Fragmentation of 4-Picolyl- and N-Methyl-4-picolinium Esters Triggered by Photochemical Electron Transfer

  摘要：

  Photochemical reduction of several 4-picolyl- and N-methyl-4-picolinium esters was examined using product analysis, laser flash photolysis, and fluorescence quenching. It is demonstrated that the radical (anions) formed in these reactions readily fragment to yield a carboxylic acid and a 4-pyridylmethyl radical intermediate. The high chemical and quantum yields observed for these photoreactions suggests that these esters can be used as photolabile protecting groups.

  DOI：

  10.1021/jo049501j

文献信息

• Visible Light Photorelease of Carboxylic Acids via Charge-Transfer Excitation of <i>N</i>-Methylpyridinium Iodide Esters
  作者：David J. Kunsberg、Allison H. Kipping、Daniel E. Falvey

  DOI：10.1021/acs.orglett.5b01490

  日期：2015.7.17

  Iodide contrast sensitization to direct irradiation of charge transfer salts incurs carboxylic acid release via visible light absorption. The photochemical reduction of N-methyl-4-pyridinium iodide esters to release carboxylic acids is examined using H-1 NMR analysis. Photolysis reactions are carried out under mild, biphasic solvent conditions, using a household LED lamp. Carboxylic acid release is reported in high yields, and the viability of this method for synthetic chemistry is demonstrated through a macroscale reaction.
• C−O Bond Fragmentation of 4-Picolyl- and <i>N</i>-Methyl-4-picolinium Esters Triggered by Photochemical Electron Transfer
  作者：Chitra Sundararajan、Daniel E. Falvey

  DOI：10.1021/jo049501j

  日期：2004.8.1

  Photochemical reduction of several 4-picolyl- and N-methyl-4-picolinium esters was examined using product analysis, laser flash photolysis, and fluorescence quenching. It is demonstrated that the radical (anions) formed in these reactions readily fragment to yield a carboxylic acid and a 4-pyridylmethyl radical intermediate. The high chemical and quantum yields observed for these photoreactions suggests that these esters can be used as photolabile protecting groups.