2-(2-chloroallyloxy)-tetrahydropyran | 918788-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(2-chloroallyloxy)-tetrahydropyran
• 英文别名: 2H-Pyran, 2-[(2-chloro-2-propen-1-yl)oxy]tetrahydro-；2-(2-chloroprop-2-enoxy)oxane
• CAS: 918788-83-7
• 化学式: C₈H₁₃ClO₂
• 分子量: 176.643
• InChiKey: RZTSWPTVBWMJTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-chloroallyloxy)-tetrahydropyran 、 1-萘硼酸 在 bis(η3-allyl-μ-chloropalladium(II)) cis,cis,cis-1,2,3,4-tetrakis (diphenylphosphinomethyl)cyclopentane 、 potassium carbonate 作用下， 以 xylene 为溶剂， 反应 20.0h， 以38%的产率得到2-(2-naphthalen-1-yl-allyloxy)tetrahydropyran
  参考文献：
  名称：

  Suzuki Coupling of 2‐Chloroacrylonitrile, Methyl 2‐Chloroacrylate, or 2‐Chloroprop‐1‐en‐3‐ol with Arylboronic Acids Catalyzed by a Palladium‐Tetraphosphine Complex

  摘要：

  The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane (Tedicyp) in combination with [Pd(C3H5)Cl](2) affords an efficient catalyst of the coupling of 2-chloroacrylonitrile with arylboronic acids. In the presence of 1% catalyst, the 2-arylacrylonitrile derivatives were obtained in medium to good yields. A variety of substituents such as alkyl, methoxy, fluoro, trifluoromethyl, formyl, or nitro on the arylboronic acid are tolerated. The cross-coupling reactions of methyl 2-chloroacrylate with arylboronic acids give simple access to 2-phenylacrylate derivatives, which are useful precursors for the synthesis of biologically active compounds such as ibuprofen, ketoprofen, and naproxen.

  DOI：

  10.1080/00397910600773866

文献信息

• Suzuki Coupling of 2‐Chloroacrylonitrile, Methyl 2‐Chloroacrylate, or 2‐Chloroprop‐1‐en‐3‐ol with Arylboronic Acids Catalyzed by a Palladium‐Tetraphosphine Complex
  作者：Florian Berthiol、Henri Doucet、Maurice Santelli

  DOI：10.1080/00397910600773866

  日期：2006.10

  The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane (Tedicyp) in combination with [Pd(C3H5)Cl](2) affords an efficient catalyst of the coupling of 2-chloroacrylonitrile with arylboronic acids. In the presence of 1% catalyst, the 2-arylacrylonitrile derivatives were obtained in medium to good yields. A variety of substituents such as alkyl, methoxy, fluoro, trifluoromethyl, formyl, or nitro on the arylboronic acid are tolerated. The cross-coupling reactions of methyl 2-chloroacrylate with arylboronic acids give simple access to 2-phenylacrylate derivatives, which are useful precursors for the synthesis of biologically active compounds such as ibuprofen, ketoprofen, and naproxen.