methyl 2-{[3-(4-chlorophenyl)-3-oxopropanthioyl]amino}acetate | 881891-97-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-{[3-(4-chlorophenyl)-3-oxopropanthioyl]amino}acetate
• 英文别名: methyl 2-[[3-(4-chlorophenyl)-3-oxopropanethioyl]amino]acetate
• CAS: 881891-97-0
• 化学式: C₁₂H₁₂ClNO₃S
• 分子量: 285.751
• InChiKey: VPOIASRMRXOYEH-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  426.4±55.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-{[3-(4-chlorophenyl)-3-oxopropanthioyl]amino}acetate 在 potassium carbonate 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 10.5h， 生成 methyl 3-(4-chlorophenyl)-5-(ethylsulfanyl)-4-formyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  An efficient synthesis of highly substituted pyrroles from β-oxodithiocarboxylates

  摘要：

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinate hydrochlorides with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in presence of chloromethyleneiminium salt derived from POCl3/DMF to afford alkyl-3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. Alkyl-3-aryl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates were formed in moderate yields when the same N,S-acetals were treated with DBU. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.076
• 作为产物：
  描述：

  对氯苯乙酮 在 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 methyl 2-{[3-(4-chlorophenyl)-3-oxopropanthioyl]amino}acetate
  参考文献：
  名称：

  An efficient synthesis of highly substituted pyrroles from β-oxodithiocarboxylates

  摘要：

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinate hydrochlorides with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in presence of chloromethyleneiminium salt derived from POCl3/DMF to afford alkyl-3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. Alkyl-3-aryl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates were formed in moderate yields when the same N,S-acetals were treated with DBU. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.076

文献信息

• An efficient synthesis of highly substituted pyrroles from β-oxodithiocarboxylates
  作者：Paulson Mathew、C.V. Asokan

  DOI：10.1016/j.tet.2005.11.076

  日期：2006.2

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinate hydrochlorides with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in presence of chloromethyleneiminium salt derived from POCl3/DMF to afford alkyl-3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. Alkyl-3-aryl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates were formed in moderate yields when the same N,S-acetals were treated with DBU. (c) 2005 Elsevier Ltd. All rights reserved.