methyl 2-cyano-3-(thienyl)acrylate

• 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: methyl 2-cyano-3-(thienyl)acrylate
• 英文别名: Methyl 2-cyano-3-thiophen-3-ylprop-2-enoate
• 化学式: C₉H₇NO₂S
• 分子量: 193.226
• InChiKey: BBWRETCASAWRII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-cyano-3-(thienyl)acrylate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 异丙醇 为溶剂， 50.0 ℃ 、446.08 kPa 条件下， 反应 41.0h， 以89%的产率得到methyl 2-cyano-3-(3-thienyl)propionate
  参考文献：
  名称：

  The Chemical Development of CI-972 and CI-1000:  A Continuous Nitration, A MgCl₂/Et₃N-Mediated C-Alkylation of a Chloronitropyrimidine, A Catalytic Protodediazotization of a Diazonium Salt, and an Air Oxidation of an Amine

  摘要：

  Efficient, large-scale processes were developed for the preparation of the potent PNP inhibitors 2,6-diamino-3,5-dihydro-7-(3-thienylmethyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one hydrochloride, monohydrate (1) and 2-amino-3,5-dihydro-7-(3-thienylmethyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one hydrochloride, monohydrate (2), We report (1) a safe, continuous nitration process for the preparation of 2-amino-6-chloro-5-nitro-4-pyrimidinol (8a) and its stable diisopropylamine salt (8b), (2) the first MgCl2/ Et3N-mediated C-alkylation of a chloronitropyrimidine, (3) a rare catalytic protodediazotization of the diazonium salt 2-amino-4-oxo-7-thiophen-3-ylmethyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-6-diazonium chloride (14), (4) a single-step process to prepare 2 directly from 2-amino-6-hydroxy-5-nitro-alpha-(3-thienylmethyl)-4-pyrimidineacetonitrile (12) using a sponge nickel-catalyzed reduction, and (5) a method to convert the over-reduction by-product 2,5-diamino-6-(1-aminomethyl-2-thiophen-3-yl-ethyl)-pyrimidin-4-ol (16) into 2 using air oxidation.

  DOI：

  10.1021/op000298d
• 作为产物：
  描述：

  3-噻吩甲醛 、 氰乙酸甲酯 在 二异丙胺 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 以93%的产率得到methyl 2-cyano-3-(thienyl)acrylate
  参考文献：
  名称：

  The Chemical Development of CI-972 and CI-1000:  A Continuous Nitration, A MgCl₂/Et₃N-Mediated C-Alkylation of a Chloronitropyrimidine, A Catalytic Protodediazotization of a Diazonium Salt, and an Air Oxidation of an Amine

  摘要：

  Efficient, large-scale processes were developed for the preparation of the potent PNP inhibitors 2,6-diamino-3,5-dihydro-7-(3-thienylmethyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one hydrochloride, monohydrate (1) and 2-amino-3,5-dihydro-7-(3-thienylmethyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one hydrochloride, monohydrate (2), We report (1) a safe, continuous nitration process for the preparation of 2-amino-6-chloro-5-nitro-4-pyrimidinol (8a) and its stable diisopropylamine salt (8b), (2) the first MgCl2/ Et3N-mediated C-alkylation of a chloronitropyrimidine, (3) a rare catalytic protodediazotization of the diazonium salt 2-amino-4-oxo-7-thiophen-3-ylmethyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-6-diazonium chloride (14), (4) a single-step process to prepare 2 directly from 2-amino-6-hydroxy-5-nitro-alpha-(3-thienylmethyl)-4-pyrimidineacetonitrile (12) using a sponge nickel-catalyzed reduction, and (5) a method to convert the over-reduction by-product 2,5-diamino-6-(1-aminomethyl-2-thiophen-3-yl-ethyl)-pyrimidin-4-ol (16) into 2 using air oxidation.

  DOI：

  10.1021/op000298d