3-cyanomethyl-7-fluorophthalide | 1315232-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-cyanomethyl-7-fluorophthalide
• 英文别名: 2-(4-fluoro-3-oxo-1H-2-benzofuran-1-yl)acetonitrile
• CAS: 1315232-91-7
• 化学式: C₁₀H₆FNO₂
• 分子量: 191.162
• InChiKey: UXHWRMVZPGAFFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙烯腈 、 邻氟苯甲酸 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 copper(II) acetate monohydrate 作用下， 以 水 为溶剂， 反应 16.0h， 以79%的产率得到3-cyanomethyl-7-fluorophthalide
  参考文献：
  名称：

  Recyclable and Reusable [RuCl₂(p-cymene)]₂/Cu(OAc)₂/PEG-400/H₂O System for Oxidative C–H Bond Alkenylations: Green Synthesis of Phthalides

  摘要：

  [RuCl2(p-cymene)](2) in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be an extremely efficient catalyst for the cross-dehydrogenative C-H bond alkenylation reaction between benzoic acids and alkenes. The reaction could be conducted at 80 degrees C using Cu(OAc)(2). H2O as oxidant, yielding a variety of phthalide derivatives in good to excellent yields. More importantly, both [RuCl2(p-cymene)](2) and Cu(OAc)(2) in the PEG-400/H2O system could be easily recycled and reused six times without any loss of catalytic activity.

  DOI：

  10.1021/acs.joc.5b01388

文献信息

• Ruthenium-Catalyzed Oxidative C–H Bond Alkenylations in Water: Expedient Synthesis of Annulated Lactones
  作者：Lutz Ackermann、Jola Pospech

  DOI：10.1021/ol201563r

  日期：2011.8.19

  Ruthenium-catalyzed cross-dehydrogenative C-H bond alkenylations occurred efficiently in environmentally benign water, which was exploited for an oxidative phthalide synthesis with ample scope. Mechanistic studies provided strong evidence for the oxidative alkenylation to proceed by an irreversible C-H bond metalation via acetate assistance.
• Recyclable and Reusable [RuCl₂(<i>p</i>-cymene)]₂/Cu(OAc)₂/PEG-400/H₂O System for Oxidative C–H Bond Alkenylations: Green Synthesis of Phthalides
  作者：Hong Zhao、Tinli Zhang、Tao Yan、Mingzhong Cai

  DOI：10.1021/acs.joc.5b01388

  日期：2015.9.4

  [RuCl2(p-cymene)](2) in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be an extremely efficient catalyst for the cross-dehydrogenative C-H bond alkenylation reaction between benzoic acids and alkenes. The reaction could be conducted at 80 degrees C using Cu(OAc)(2). H2O as oxidant, yielding a variety of phthalide derivatives in good to excellent yields. More importantly, both [RuCl2(p-cymene)](2) and Cu(OAc)(2) in the PEG-400/H2O system could be easily recycled and reused six times without any loss of catalytic activity.