diethyl [3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)methylphosphonate | 1311229-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl [3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)methylphosphonate
• 英文别名: Diethyl [3-(benzofuran-2-yl)-1-phenyl-1h-pyrazol-4-yl](3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)methylphosphonate；2-[[[3-(1-benzofuran-2-yl)-1-phenylpyrazol-4-yl]-diethoxyphosphorylmethyl]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile
• CAS: 1311229-35-2
• 化学式: C₃₁H₃₁N₄O₄PS
• 分子量: 586.651
• InChiKey: NORWYPPQDUSKJV-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  797.9±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl [3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)methylphosphonate 在 iron(III) chloride 作用下， 以 四氢呋喃 为溶剂， 170.0~180.0 ℃ 、1.3 kPa 条件下， 反应 0.5h， 生成 dimethyl [3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)methylphosphonate
  参考文献：
  名称：

  Multicomponent reactions in a one-pot synthesis of α-aminophosphonates and α-aminophosphonic diamides with anti-inflammatory properties

  摘要：

  Schiff-base Kabachnik-Fields intermediates generated in situ from substituted pyrazole-4-carbaldehyde and 2-aminothiophene derivatives were trapped by dialkyl phosphites to produce the corresponding alpha-aminophosphonates in moderate yields. The latter products could be also obtained in excellent yields (a parts per thousand yen75%) by directly applying the phosphorus reagents to the Schiff bases. Next, dialkyl phosphites were applied to one of the parent aldehydes to give the expected alpha-hydroxyphosphonate derivatives. Applying hexaalkyl triamidophosphites to the Schiff base in ethanol afforded methylphosphonic diamide derivatives, whereas ring attack on the pyrazole ring occurred when the same amidophosphites were applied to the parent aldehyde to give the corresponding alkylidenephosphorane ylides in an open structure form in good yields. Some of the new compounds exhibited considerable anti-inflammatory properties.

  DOI：

  10.1007/s00706-011-0492-8
• 作为产物：
  描述：

  3-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 在 iron(III) chloride 、 硫酸 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 diethyl [3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)methylphosphonate
  参考文献：
  名称：

  Multicomponent reactions in a one-pot synthesis of α-aminophosphonates and α-aminophosphonic diamides with anti-inflammatory properties

  摘要：

  Schiff-base Kabachnik-Fields intermediates generated in situ from substituted pyrazole-4-carbaldehyde and 2-aminothiophene derivatives were trapped by dialkyl phosphites to produce the corresponding alpha-aminophosphonates in moderate yields. The latter products could be also obtained in excellent yields (a parts per thousand yen75%) by directly applying the phosphorus reagents to the Schiff bases. Next, dialkyl phosphites were applied to one of the parent aldehydes to give the expected alpha-hydroxyphosphonate derivatives. Applying hexaalkyl triamidophosphites to the Schiff base in ethanol afforded methylphosphonic diamide derivatives, whereas ring attack on the pyrazole ring occurred when the same amidophosphites were applied to the parent aldehyde to give the corresponding alkylidenephosphorane ylides in an open structure form in good yields. Some of the new compounds exhibited considerable anti-inflammatory properties.

  DOI：

  10.1007/s00706-011-0492-8