Ethyl 3-methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate | 140834-72-6

• 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 3-methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate
• 英文别名: ethyl 3-perfluorohexylbutanoate；3-Methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoic acid ethyl ester；ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-3-methylnonanoate
• CAS: 140834-72-6
• 化学式: C₁₂H₁₁F₁₃O₂
• 分子量: 434.197
• InChiKey: OMBNNWKRMVXNBV-UHFFFAOYSA-N

物化性质

• 沸点：
  209.1±35.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 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：

  2-丁烯酸乙酯 、 全氟己基碘烷 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 7.0h， 以61%的产率得到Ethyl 3-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

• 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.