3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylenehexanoate

• 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: 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylenehexanoate
• 英文别名: 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl 2-methylidenehexanoate；3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylidenehexanoate
• 化学式: C₁₅H₁₅F₁₃O₂
• 分子量: 474.262
• InChiKey: ILBMQNICIDGPDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  一氧化碳 、 3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟-1-辛醇 、 1-己炔 在 甲烷磺酸 、 二苯基-2-吡啶膦 、 palladium diacetate 作用下， 以 二氯甲烷 为溶剂， 70.0 ℃ 、3.04 MPa 条件下， 反应 3.0h， 生成 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylenehexanoate
  参考文献：
  名称：

  Fluorinated acrylates via alkoxycarbonylation of 1-alkynes with fluorinated alcohols

  摘要：

  The system formed by combining in situ Pd(OAc)2 with (2-pyridyl)diphenylphosphine (PyPPII2) and CH3SO3H catalyzes efficiently the carbonylation of terminal alkynes (phenylacetylene or 1-hexyne) with alcohols having perfluorinated segments of the type CF3(CF2)(m)(CH2)(n)-OH (m=1 or 3, n=1, 2 or 3) or with pentafluorophenol. Good carbonylation rates accompanied by high regioselectivity towards acrylate ester formation are obtained under mild reaction conditions (T=60-80 degrees C, P(CO)=30 atm). The influence of the CO pressure, the catalyst composition, the temperature and the number (n) of protonated methylene groups on the catalysis has been studied. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.123

文献信息

• Fluorinated acrylates via alkoxycarbonylation of 1-alkynes with fluorinated alcohols
  作者：Alberto Scrivanti、Matteo Bertoldini、Manuela Aversa、Valentina Beghetto、Aurora Zancanaro、Stefano Paganelli、Ugo Matteoli

  DOI：10.1016/j.tet.2014.06.123

  日期：2014.9

  The system formed by combining in situ Pd(OAc)2 with (2-pyridyl)diphenylphosphine (PyPPII2) and CH3SO3H catalyzes efficiently the carbonylation of terminal alkynes (phenylacetylene or 1-hexyne) with alcohols having perfluorinated segments of the type CF3(CF2)(m)(CH2)(n)-OH (m=1 or 3, n=1, 2 or 3) or with pentafluorophenol. Good carbonylation rates accompanied by high regioselectivity towards acrylate ester formation are obtained under mild reaction conditions (T=60-80 degrees C, P(CO)=30 atm). The influence of the CO pressure, the catalyst composition, the temperature and the number (n) of protonated methylene groups on the catalysis has been studied. (C) 2014 Elsevier Ltd. All rights reserved.