ethyl 2-(1,3-dioxoisoindolin-2-yl)-3-perfluorohexylpropanoate | 1274722-66-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(1,3-dioxoisoindolin-2-yl)-3-perfluorohexylpropanoate
• 英文别名: ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-(1,3-dioxoisoindolin-2-yl)nonanoate；Ethyl 2-(1,3-dioxoisoindol-2-yl)-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate
• CAS: 1274722-66-5
• 化学式: C₁₉H₁₂F₁₃NO₄
• 分子量: 565.288
• InChiKey: MDVCSXIAUUTLFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1,3-dioxoisoindolin-2-yl)-3-perfluorohexylpropanoate 在 一水合肼 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以66%的产率得到Ethyl 2-amino-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate
  参考文献：
  名称：

  Photoinduced radical hydroperfluoroalkylation and the synthesis of fluorinated amino acids and peptides

  摘要：

  The photoinduced radical hydroperfluoroalkylation of unsaturated carboxylic acids using TTMSS as a H-donor was successfully developed. The stereoselective reaction using Oppolzer's camphorsultum was also achieved to give high stereoselectivity. The reaction was also effective for N-phthalimide-dehydroamino acid and the product was easily converted to the corresponding amino acid and a peptide derivative. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.02.019
• 作为产物：
  描述：

  全氟己基碘烷 、 ethyl α-phthalimidoacrylate 在 三(三甲基硅基)硅烷 、 sodium thiosulfate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以78%的产率得到ethyl 2-(1,3-dioxoisoindolin-2-yl)-3-perfluorohexylpropanoate
  参考文献：
  名称：

  Photoinduced radical hydroperfluoroalkylation and the synthesis of fluorinated amino acids and peptides

  摘要：

  The photoinduced radical hydroperfluoroalkylation of unsaturated carboxylic acids using TTMSS as a H-donor was successfully developed. The stereoselective reaction using Oppolzer's camphorsultum was also achieved to give high stereoselectivity. The reaction was also effective for N-phthalimide-dehydroamino acid and the product was easily converted to the corresponding amino acid and a peptide derivative. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.02.019

文献信息

• Eosin Y-Catalyzed Visible-Light-Induced Hydroperfluoroalkylation of Electron-Deficient Alkenes
  作者：Satsuki Shigenaga、Haruko Shibata、Koto Tagami、Tadashi Kanbara、Tomoko Yajima

  DOI：10.1021/acs.joc.2c01827

  日期：2022.11.4

  eosin Y-catalyzed hydroperfluoroalkylation of electron-deficient alkenes is described herein. The reaction proceeded smoothly under visible light irradiation and selectively afforded a hydroperfluoroalkylated product. Various perfluoroalkyl bromides and electron-deficient olefins can be used in this reaction, and all chemicals required for this reaction are safe and readily available.

  本文描述了缺电子烯烃的曙红Y催化的氢全氟烷基化。反应在可见光照射下顺利进行，选择性地得到氢全氟烷基化产物。该反应可以使用各种全氟烷基溴和缺电子烯烃，并且该反应所需的所有化学品都是安全且易于获得的。