5-甲酰基-4-甲基-3-(戊-4-烯氧基)-1H-吡咯-2-羧酸乙酯 | 1020414-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 5-甲酰基-4-甲基-3-(戊-4-烯氧基)-1H-吡咯-2-羧酸乙酯
• 英文名称: ethyl 5-formyl-4-methyl-3-(pent-4-enyloxy)-1H-pyrrole-2-carboxylate
• 英文别名: ethyl 5-formyl-4-methyl-3-pent-4-enoxy-1H-pyrrole-2-carboxylate
• CAS: 1020414-47-4
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: WQCYLIJUYFFXTA-UHFFFAOYSA-N

物化性质

• 熔点：
  49 °C
• 沸点：
  436.4±45.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-甲酰基-4-甲基-3-(戊-4-烯氧基)-1H-吡咯-2-羧酸乙酯 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以100%的产率得到(R)-ethyl 4-methyl-5-[(2-methylpropan-2-ylsulfinyl)iminomethyl]-3-pent-4-enyloxy-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis and structure of a heterocyclic ansa pyrrole amino acid

  摘要：

  We report a synthetic route to ansa pyrrole amino acids via olefin ring-closing metathesis of diene precursors in the presence of Grubbs I catalyst. The dienes were prepared by Grignard addition to pyrrole sulfinyl imines. The success of the macrocyclic ring closure depends oil the dienes structure and only in the case of the 13-membered compound 28 sufficient material could be isolated by preparative HPLC separation to investigate its structure spectroscopically. As also rationalized by our computations at the B3LYP/6-311+G(d,p)//B3LYP/6-31G(d) level of theory, 28 is configurationally stable. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.061
• 作为产物：
  描述：

  4-甲基-3-(戊-4-烯氧基)-1H-吡咯-2-羧酸乙酯 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以84%的产率得到5-甲酰基-4-甲基-3-(戊-4-烯氧基)-1H-吡咯-2-羧酸乙酯
  参考文献：
  名称：

  Synthesis and structure of a heterocyclic ansa pyrrole amino acid

  摘要：

  We report a synthetic route to ansa pyrrole amino acids via olefin ring-closing metathesis of diene precursors in the presence of Grubbs I catalyst. The dienes were prepared by Grignard addition to pyrrole sulfinyl imines. The success of the macrocyclic ring closure depends oil the dienes structure and only in the case of the 13-membered compound 28 sufficient material could be isolated by preparative HPLC separation to investigate its structure spectroscopically. As also rationalized by our computations at the B3LYP/6-311+G(d,p)//B3LYP/6-31G(d) level of theory, 28 is configurationally stable. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.061