4-picolyl p-tolylacetate | 756878-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-picolyl p-tolylacetate
• 英文别名: picolyl p-tolylacetate；Pyridin-4-ylmethyl 2-(4-methylphenyl)acetate；pyridin-4-ylmethyl 2-(4-methylphenyl)acetate
• CAS: 756878-68-9
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: CAIUTCYPDLKYMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  4-picolyl p-tolylacetate 在 silver perchlorate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 生成 N-methyl picolinium p-tolylacetate 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 、 对甲基苯乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以73%的产率得到4-picolyl p-tolylacetate
  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

• Photolytic Release of Carboxylic Acids Using Linked Donor−Acceptor Molecules:  Direct versus Mediated Photoinduced Electron Transfer to <i>N</i>-Alkyl-4-picolinium Esters
  作者：Chitra Sundararajan、Daniel E. Falvey

  DOI：10.1021/ol050744n

  日期：2005.6.1

  [reaction: see text] Efficient photorelease (Phi = 0.7) of carboxylic acids is achieved with a covalently linked mediator (benzophenone) protecting group (N-alkyl-4-picolinium ester) molecule. The mechanism involves initial photoreduction of the mediator, followed by rapid electron transfer to the protecting group.

  [反应：见正文]用共价连接的介体（二苯甲酮）保护基团（N-烷基-4-吡啶啉酯）分子可实现羧酸的有效光释放（Phi = 0.7）。该机理涉及介体的初始光还原，然后电子快速转移至保护基团。