5-(n-heptadecafluorooctyl)salicylaldehyde | 244049-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(n-heptadecafluorooctyl)salicylaldehyde
• 英文别名: 2-hydroxy-5-(perfluorooctyl)benzaldehyde；2-hydroxy-5-perfluorooctylbenzaldehyde；5-(Heptadecafluorooctyl)salicylaldehyde；5-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)-2-hydroxybenzaldehyde
• CAS: 244049-59-0
• 化学式: C₁₅H₅F₁₇O₂
• 分子量: 540.176
• InChiKey: RYBNVIHCWYMHJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  5-(n-heptadecafluorooctyl)salicylaldehyde 在 溴 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-isopropoxy-3-bromo-5-(perfluorooctyl)benzaldehyde
  参考文献：
  名称：

  通过在双齿配体上引入轻质荧光标签而活化的格鲁布斯-霍维达第二代催化剂

  摘要：

  摘要 制备了由配体上的氟标签活化的各种新型Grubbs-Hoveyda第二代催化剂。在所研究的2-烯丙基-2-（2-甲基烯丙基）丙二酸乙酯的闭环复分解反应催化剂中，在二齿配体上带有1-萘基的催化剂表现出最高的催化活性。 制备了由配体上的氟标签活化的各种新型Grubbs-Hoveyda第二代催化剂。在所研究的2-烯丙基-2-（2-甲基烯丙基）丙二酸乙酯的闭环复分解反应催化剂中，在二齿配体上带有1-萘基的催化剂表现出最高的催化活性。

  DOI：

  10.1055/s-0036-1588686
• 作为产物：
  描述：

  4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-十七氟辛基)苯酚 在 4-二甲氨基吡啶 、 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 1.0h， 生成 5-(n-heptadecafluorooctyl)salicylaldehyde
  参考文献：
  名称：

  Pozzi, Gianluca; Cavazzini, Marco; Cinato, Flavio, European Journal of Organic Chemistry, 1999, # 8, p. 1947 - 1955

  摘要：

  DOI：

文献信息

• Direct perfluoroalkylation of non-activated aromatic C–H bonds of phenols
  作者：Masato Matsugi、Masakazu Hasegawa、Shohei Hasebe、Shohei Takai、Ryusuke Suyama、Yusuke Wakita、Kanako Kudo、Hiromi Imamura、Toshiya Hayashi、Seiichi Haga

  DOI：10.1016/j.tetlet.2008.04.106

  日期：2008.6

  A simple procedure for the perfluoroalkylation of the aromatic ring of phenols under mildly basic conditions is described. Treatment of a variety of phenols with perfluoroalkyl iodide in the presence of the radical initiator V-70L and Cs2CO3 provided the corresponding perfluoroalkylated products in moderate to good yields. Generally, the reaction proceeded smoothly at room temperature to yield regioselectively

  描述了在温和碱性条件下苯酚芳环全氟烷基化的简单程序。在自由基引发剂V-70L和Cs 2 CO 3的存在下用全氟烷基碘处理各种酚，以中等至良好的产率提供了相应的全氟烷基化产物。通常，反应在室温下平稳进行，得到区域选择性的全氟烷基化产物。
• Activation of Grubbs–Hoveyda Second-Generation Catalysts Employing Aromatic Ligands Bearing a Widespread Aryl Substituent
  作者：Masato Matsugi、Yuki Kobayashi、Rina Igarashi、Yuta Ishikawa、Kento Shimowaki、Yuya Sugiyama、Takayuki Shioiri、Sae Inukai

  DOI：10.3987/com-18-s(t)56

  日期：——

  In this study, an activation strategy for Grubbs-Hoveyda second-generation-type catalysts by utilizing the intramolecular steric strain on the ligands is described. The variant, which is expected to exhibit intramolecular steric strain, containing extensively spread aromatic and alkoxy groups in the ligand structure was prepared and examined. The combination of tricyclic anthracenyl and isopropoxy groups are observed to exhibit the highest catalytic activity among these synthetic catalysts. The activated catalyst was successfully used in a ring-closing metathesis reaction depicting a catalyst loading of the order of 20 mol ppm in dry benzene. The X-ray crystallographic analysis suggests the existence of an intramolecular CH/pi interaction between the sp(2) carbon of the anthracenyl group and the methyne hydrogen of the isopropoxy group.
• Synthesis and RCM Reactions Using a Recyclable Grubbs−Hoveyda Metathesis Catalyst Activated by a Light Fluorous Tag
  作者：Masato Matsugi、Yuki Kobayashi、Naoki Suzumura、Yuki Tsuchiya、Takayuki Shioiri

  DOI：10.1021/jo101140w

  日期：2010.11.19

  A recyclable Grubbs-Hoveyda second-generation catalyst activated by a light fluorous tag was prepared The modified light fluorous catalyst exhibited higher catalytic activity than the parent or the previously reported light fluorous variant for RCM reactions and could be routinely recovered The light fluorous tag incorporated in the catalyst served as both an activator as well as a handle for separation and recovery with fluorous solid-phase extraction
• Pozzi, Gianluca; Cavazzini, Marco; Cinato, Flavio, European Journal of Organic Chemistry, 1999, # 8, p. 1947 - 1955
  作者：Pozzi, Gianluca、Cavazzini, Marco、Cinato, Flavio、Montanari, Fernando、Quici, Silvio

  DOI：——

  日期：——
• Grubbs–Hoveyda Second-Generation Catalysts Activated by the Introduction of a Light Fluorous Tag onto the Bidentate Ligands
  作者：Masato Matsugi、Yuki Kobayashi、Naoki Suzumura、Yuki Tsuchiya、Machiko Goto、Yuya Sugiyama、Takayuki Shioiri

  DOI：10.1055/s-0036-1588686

  日期：——

  second-generation catalysts activated by a fluorous tag on the ligands were prepared. The catalyst bearing the 1-naphthyl group on the bidentate ligand exhibited the highest catalytic activity among the studied catalysts for the ring-closing­-metathesis reaction of diethyl 2-allyl-2-(2-methylallyl)malonate. Various novel Grubbs–Hoveyda second-generation catalysts activated by a fluorous tag on the ligands

  摘要 制备了由配体上的氟标签活化的各种新型Grubbs-Hoveyda第二代催化剂。在所研究的2-烯丙基-2-（2-甲基烯丙基）丙二酸乙酯的闭环复分解反应催化剂中，在二齿配体上带有1-萘基的催化剂表现出最高的催化活性。 制备了由配体上的氟标签活化的各种新型Grubbs-Hoveyda第二代催化剂。在所研究的2-烯丙基-2-（2-甲基烯丙基）丙二酸乙酯的闭环复分解反应催化剂中，在二齿配体上带有1-萘基的催化剂表现出最高的催化活性。