2-(3-thienyl)acrylonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(3-thienyl)acrylonitrile
• 英文别名: 2-Thiophen-3-ylprop-2-enenitrile
• 化学式: C₇H₅NS
• 分子量: 135.189
• InChiKey: UNWGCCCUEBEIQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-噻吩硼酸 、 2-氯丙烯腈 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15%的产率得到2-(3-thienyl)acrylonitrile
  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

• US4139641A
  申请人：——

  公开号：US4139641A

  公开（公告）日：1979-02-13
• 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.