ethyl 4-acetyl-5-methyl-3-propyl-1H-pyrrole-2-carboxylate | 218774-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-acetyl-5-methyl-3-propyl-1H-pyrrole-2-carboxylate
• 英文别名: 4-acetyl-5-methyl-3-propyl-pyrrole-2-carboxylic acid ethyl ester；4-Acetyl-5-methyl-3-propyl-pyrrol-2-carbonsaeure-aethylester
• CAS: 218774-44-8
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: JHVXIAGNXPBNMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-acetyl-5-methyl-3-propyl-1H-pyrrole-2-carboxylate 在 sodium hydroxide 、 sodium tetrahydroborate 、 甲酸 、 三氟化硼乙醚 、 双氧水 、 溴 、 四氯苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 49.25h， 生成 3,8,12,17-tetraethyl-7,13-dimethyl-2,18-dipropyl-1,19,21,24-tetrahydro-1,19-bilindione
  参考文献：
  名称：

  Helical Chirality Induction in Zinc Bilindiones by Amino Acid Esters and Amines

  摘要：

  Complexation of alpha-amino acid esters, beta-amino ethers, and amines with a series of zinc 1,19-bilindione derivatives was studied, particularly focusing on the helical chirality induction in the bilindione framework triggered by the binding of chiral guests. Comparative studies of binding and helical chirality induction indicated that binding and chiral induction were markedly affected by polar substituents present in both zinc bilindiones and guests. 2-Hydroxyethyl groups at the 2,18-positions of zinc bilindione largely assisted the binding of amines and amino acid esters but not the chiral induction. 19O-Alkylation of the zinc bilindiones had inhibitory effects on the binding but enhanced efficiency of helical chirality induction. The enantiomeric excess of 19O-alkyl zinc bilindione complexed with L-Trp-OMe in CD2Cl2 was 73% at 223 K. A COOR group and an aromatic group in the guest promoted helical chirality induction of 19O-alkylated zinc bilindiones. The patterns of H-1 NMR complexation-induced shifts of zinc bilindiones and guests and a molecular modeling study of the complexes showed that electrostatic repulsion between the COOR group of amino acid esters and the lactam ring of zinc bilindiones, and stacking of the side chain groups of amino acid esters on the C ring of zinc bilindione made a significant contribution to efficient helical chirality induction.

  DOI：

  10.1021/jo980819j
• 作为产物：
  描述：

  丁酰乙酸乙酯 、 乙酰丙酮 在 溶剂黄146 、 锌 、 sodium nitrite 作用下， 生成 ethyl 4-acetyl-5-methyl-3-propyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Fischer; Goldschmidt; Nuessler, Justus Liebigs Annalen der Chemie, 1931, vol. 486, p. 33

  摘要：

  DOI：

文献信息

• Fischer; Goldschmidt; Nuessler, Justus Liebigs Annalen der Chemie, 1931, vol. 486, p. 33
  作者：Fischer、Goldschmidt、Nuessler

  DOI：——

  日期：——
• Helical Chirality Induction in Zinc Bilindiones by Amino Acid Esters and Amines
  作者：Tadashi Mizutani、Shigeyuki Yagi、Atsushi Honmaru、Shinji Murakami、Masaru Furusyo、Toru Takagishi、Hisanobu Ogoshi

  DOI：10.1021/jo980819j

  日期：1998.11.1

  Complexation of alpha-amino acid esters, beta-amino ethers, and amines with a series of zinc 1,19-bilindione derivatives was studied, particularly focusing on the helical chirality induction in the bilindione framework triggered by the binding of chiral guests. Comparative studies of binding and helical chirality induction indicated that binding and chiral induction were markedly affected by polar substituents present in both zinc bilindiones and guests. 2-Hydroxyethyl groups at the 2,18-positions of zinc bilindione largely assisted the binding of amines and amino acid esters but not the chiral induction. 19O-Alkylation of the zinc bilindiones had inhibitory effects on the binding but enhanced efficiency of helical chirality induction. The enantiomeric excess of 19O-alkyl zinc bilindione complexed with L-Trp-OMe in CD2Cl2 was 73% at 223 K. A COOR group and an aromatic group in the guest promoted helical chirality induction of 19O-alkylated zinc bilindiones. The patterns of H-1 NMR complexation-induced shifts of zinc bilindiones and guests and a molecular modeling study of the complexes showed that electrostatic repulsion between the COOR group of amino acid esters and the lactam ring of zinc bilindiones, and stacking of the side chain groups of amino acid esters on the C ring of zinc bilindione made a significant contribution to efficient helical chirality induction.