methyl pyruvate 1-naphthylhydrazone | 139975-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl pyruvate 1-naphthylhydrazone
• CAS: 139975-68-1
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: KVVJIMOUDGHWKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.69
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl pyruvate 1-naphthylhydrazone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到methyl benzindole-2-carboxylate
  参考文献：
  名称：

  Synthesis and characterization of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate

  摘要：

  The synthesis of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate (4), is described, and its physical and chemical properties are compared to those of the trimethyl ester of PQQ (2) and the methyl ester of 7,9-didecarboxy PQQ (3). The synthesis of 4 was achieved by starting with 1-aminonaphthalene and constructing 2-carbomethoxybenz[g]indole (7) by a Japp-Klingemann reaction with methyl alpha-methylacetoacetate and a subsequent Fischer indolization reaction. The quinone function was introduced by a Fremy's salt oxidation of 5-aminoindole 9 which was prepared from 7 by regioselective nitration and catalytic hydrogenation. From the physical properties, it can be recognized that the peri pyridine nitrogen and the ester groups at the 7- and 9-positions considerably affect the electronic nature of the molecules. This is reflected on the reactivities of the quinones in the acetone-adduct formation, the reaction with phenylhydrazine, and the aerobic autorecycling oxidation of benzylamine. The significant roles of the pyridine nitrogen and the ester groups in these reactions are discussed.

  DOI：

  10.1021/jo00036a007
• 作为产物：
  描述：

  丁酸,2-甲基-2-(1-萘基偶氮)-3-羰基-,甲基酯 在 磷酸 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以54%的产率得到methyl pyruvate 1-naphthylhydrazone
  参考文献：
  名称：

  Synthesis and characterization of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate

  摘要：

  The synthesis of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate (4), is described, and its physical and chemical properties are compared to those of the trimethyl ester of PQQ (2) and the methyl ester of 7,9-didecarboxy PQQ (3). The synthesis of 4 was achieved by starting with 1-aminonaphthalene and constructing 2-carbomethoxybenz[g]indole (7) by a Japp-Klingemann reaction with methyl alpha-methylacetoacetate and a subsequent Fischer indolization reaction. The quinone function was introduced by a Fremy's salt oxidation of 5-aminoindole 9 which was prepared from 7 by regioselective nitration and catalytic hydrogenation. From the physical properties, it can be recognized that the peri pyridine nitrogen and the ester groups at the 7- and 9-positions considerably affect the electronic nature of the molecules. This is reflected on the reactivities of the quinones in the acetone-adduct formation, the reaction with phenylhydrazine, and the aerobic autorecycling oxidation of benzylamine. The significant roles of the pyridine nitrogen and the ester groups in these reactions are discussed.

  DOI：

  10.1021/jo00036a007