Ethyl 2-methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate | 140834-68-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 2-methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate
• 英文别名: ethyl 2-methyl-3-perfluorohexylpropanoate；ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-methylnonanoate；2-Methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoic acid ethyl ester
• CAS: 140834-68-0
• 化学式: C₁₂H₁₁F₁₃O₂
• 分子量: 434.197
• InChiKey: MKLRSRWVGBWOND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  全氟己基碘烷 、 甲基丙烯酸乙酯 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 4.0h， 以99%的产率得到Ethyl 2-methyl-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

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。
• Cobaloxime-catalyzed hydroperfluoroalkylation of electron-deficient alkenes with perfluoroalkyl halides: reaction and mechanism
  作者：Changming Hu、Yaoling Qiu

  DOI：10.1021/jo00038a022

  日期：1992.6

  Direct hydroperfluoroalkylation of electron-deficient alkenes-ethyl acrylates 4, 7, and 8, acrylonitrile (5), and methyl vinyl ketone (6)-with perfluoroalkyl halides R(f)X (1, X = I;2, X = Br) in the presence of cobaloxime(III) (3) and zinc gives 1:1 hydroperfluoroalkylation adducts in good yields. This reaction provides a convenient synthesis of beta-(perfluoroalkyl)carboxylic esters 9, 12, and 13, nitriles 10, and ketones 11. Details of the reaction including effect of solvent, temperature, and ratio of reagents were examined. The reaction is proposed to proceed via a radical mechanism initiated by low-valent cobalt.
• Photoinduced radical hydroperfluoroalkylation and the synthesis of fluorinated amino acids and peptides
  作者：Tomoko Yajima、Kanako Yamaguchi、Rie Hirokane、Emiko Nogami

  DOI：10.1016/j.jfluchem.2013.02.019

  日期：2013.6

  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.