methyl 4-acetyl-3-methoxycarbonylmethyl-5-methylpyrrole-2-carboxylate | 73869-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-acetyl-3-methoxycarbonylmethyl-5-methylpyrrole-2-carboxylate
• 英文别名: methyl (4-acetyl-2-methoxycarbonyl-5-methyl-1H-pyrrol-3-yl)acetate；Methyl 3-acetyl-5-(methoxycarbonyl)-2-methylpyrrole-4-acetate；Methyl-3-acetyl-5-methoxycarbonyl-2-methylpyrrol-4-acetat；4-Acetyl-3-methoxycarbonylmethyl-5-methyl-1H-pyrrole-2-carboxylic acid, methyl ester；methyl 4-acetyl-3-(2-methoxy-2-oxoethyl)-5-methyl-1H-pyrrole-2-carboxylate
• CAS: 73869-95-1
• 化学式: C₁₂H₁₅NO₅
• 分子量: 253.255
• InChiKey: BNKCHPNWOKORPM-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C
• 沸点：
  427.7±45.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-acetyl-3-methoxycarbonylmethyl-5-methylpyrrole-2-carboxylate 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 13.5h， 生成 2-(4-ethyl-2,5-dihydro-5-methyl-2-oxo-1H-pyrrol-3-yl)ethanol
  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：

  methyl 3-methoxycarbonylmethyl-5-methylpyrrole-2-carboxylate 、 乙酸酐 在 tin(ll) chloride 作用下， 反应 1.0h， 以2.8 g的产率得到methyl 4-acetyl-3-methoxycarbonylmethyl-5-methylpyrrole-2-carboxylate
  参考文献：
  名称：

  Chaudhry, Irshad A.; Clezy, Peter S., Australian Journal of Chemistry, 1982, vol. 35, # 6, p. 1185 - 1201

  摘要：

  DOI：

文献信息

• 2,3,7,8,12,13,17,18-Octakis(.beta.-hydroxyethyl)porphyrin (octaethanolporphyrin) and its liquid crystalline derivatives: synthesis and characterization
  作者：Brian A. Gregg、Marye Anne Fox、Allen J. Bard

  DOI：10.1021/ja00190a041

  日期：1989.4

  A synthesis is reported of 2,3,7,8,12,13,17,18-octakis(beta}-hydroxyethyl)porphyrin (octaethanolporphyrin) and a series of its octaalky ether derivatives. A number of the octakis(alkoxyethyl)porphyrins exhibit a discotic liquid crystalline phase, and all exhibit an isotropic liquid phase. These materials can be prepared as ordered thin films for testing as large-area organic semiconductor devices

  合成 2,3,7,8,12,13,17,18-octakis(β}-hydroxyethyl)porphyrin (octaethanolporphyrin) 及其一系列八烷基醚衍生物。许多八(烷氧基乙基)卟啉表现出盘状液晶相，并且都表现出各向同性液相。这些材料可以制备成有序薄膜，用于作为大面积有机半导体器件进行测试。
• Wollmann, Theo; Franck, Burchard, Angewandte Chemie, 1984, vol. 96, # 3, p. 227
  作者：Wollmann, Theo、Franck, Burchard

  DOI：——

  日期：——
• Franck, Burchhard; Wegner, Christian; Bringmann, Gerhard, Liebigs Annalen der Chemie, 1980, # 2, p. 253 - 262
  作者：Franck, Burchhard、Wegner, Christian、Bringmann, Gerhard、Fels, Gregor

  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.
• Chaudhry, Irshad A.; Clezy, Peter S., Australian Journal of Chemistry, 1982, vol. 35, # 6, p. 1185 - 1201
  作者：Chaudhry, Irshad A.、Clezy, Peter S.

  DOI：——

  日期：——