1-Acetyl-3-[1-(3,6-dimethoxy-2-nitro-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione | 912850-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Acetyl-3-[1-(3,6-dimethoxy-2-nitro-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione
• 英文别名: (3Z)-1-acetyl-3-[(3,6-dimethoxy-2-nitrophenyl)methylidene]piperazine-2,5-dione
• CAS: 912850-09-0
• 化学式: C₁₅H₁₅N₃O₇
• 分子量: 349.3
• InChiKey: VRLQIWUVFPPDES-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-Acetyl-3-[1-(3,6-dimethoxy-2-nitro-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.5h， 生成 [(4,7-Dimethoxy-1H-indole-2-carbonyl)-amino]-acetic acid
  参考文献：
  名称：

  From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics

  摘要：

  1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.095
• 作为产物：
  描述：

  1,4-二乙酰基哌嗪-2,5-二酮 、 3,6-二甲氧基-2-硝基苯甲醛 在 potassium tert-butylate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 生成 1-Acetyl-3-[1-(3,6-dimethoxy-2-nitro-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione
  参考文献：
  名称：

  From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics

  摘要：

  1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.095

文献信息

• From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics
  作者：Juan Francisco González、Elena de la Cuesta、Carmen Avendaño

  DOI：10.1016/j.tetlet.2006.07.095

  日期：2006.9

  1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.