t-butyl 2,5-dihydro-2-hydroxy-4-(2-methoxycarbonylethyl)-3-methyl-5-oxo-1H-pyrrole-2-carboxylate | 89188-55-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: t-butyl 2,5-dihydro-2-hydroxy-4-(2-methoxycarbonylethyl)-3-methyl-5-oxo-1H-pyrrole-2-carboxylate
• 英文别名: t-butyl 2,5-dihydro-2-hydroxy-4-(2-methoxycarbonylethyl)-3-methyl-5-oxopyrrole-2-carboxylate；tert-butyl 2-hydroxy-4-(3-methoxy-3-oxopropyl)-3-methyl-5-oxo-1H-pyrrole-2-carboxylate
• CAS: 89188-55-6
• 化学式: C₁₄H₂₁NO₆
• 分子量: 299.324
• InChiKey: IBLQBJYNOLXSSC-UHFFFAOYSA-N

物化性质

• 沸点：
  463.0±45.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  t-butyl 2,5-dihydro-2-hydroxy-4-(2-methoxycarbonylethyl)-3-methyl-5-oxo-1H-pyrrole-2-carboxylate 在 三乙基硅烷 、 硫酸 、 三氟化硼乙醚 、 苯甲酰氯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 340.0h， 生成 bonellin mononitrile methyl ester
  参考文献：
  名称：

  （±）-bonellin二甲基酯的全合成

  摘要：

  已通过外消旋形式通过光化学闭环形成大环的顺序，以外消旋形式合成了具有生理活性的绿色Bon子的绿色色素护角素的二甲基酯。

  DOI：

  10.1039/c39830001237
• 作为产物：
  描述：

  2-2,4-二甲基-5-(叔丁氧羰基)-3-吡咯丙酸甲酯 在 ammonium cerium (IV) nitrate 、 间氯过氧苯甲酸 作用下， 生成 t-butyl 2,5-dihydro-2-hydroxy-4-(2-methoxycarbonylethyl)-3-methyl-5-oxo-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis and properties of mesobilirubins XIIγ and XIIIγ and their mesobiliverdins

  摘要：

  The title pigments, with propionic acid groups displaced to the lactam end rings, were synthesized for the first time by the "1 + 2 + 1" approach, coupling two equivalents of a monopyrrole to a dipyrrylmethane (to give XII gamma), or the "2 + 2" approach, self-coupling two equivalents of a dipyrrinone (to give XIII gamma). Using the "1 + 2 + 1" approach, mesobilirubin III alpha was also prepared. Mesobilirubins XII gamma and XIII gamma are more polar than mesobilirubin III alpha and unlike III alpha cannot effectively engage the propionic acid groups in intramolecular hydrogen bonding to the dipyrrinone components. The new mesobilirubins give exciton coupled circular dichroism spectra in the presence of human serum albumin or quinine, with the XII gamma isomer exhibiting Cotton effect intensities nearly as strong as those from the III alpha isomer; whereas, the XIII gamma isomer exhibits far weaker intensities. Mesobilirubin III alpha requires glucuronidation for hepatobiliary elimination; whereas, XII gamma and XIII gamma do not, and they are excreted intact across the liver into bile. The corresponding biliverdins XII gamma and XIII gamma are reduced only slowly by biliverdin IX alpha reductase, in contrast to the fast reduction of the natural IX alpha isomer.

  DOI：

  10.1007/s00706-014-1160-6

文献信息

• Synthetic studies relevant to biosynthetic research on vitamin B₁₂. Part 7. Synthesis of (±)-bonellin dimethyl ester
  作者：Alan R. Battersby、Christopher J. Dutton、Christopher J. R. Fookes

  DOI：10.1039/p19880001569

  日期：——

  the green marine pigment, bonellin, has been synthesized in racemic form by a rational photochemical route. The two propionate residues of this biologically active pigment have been introduced synthetically in differentiated form which opens the way to the synthesis of the naturally occurring amino acid derivatives of bonellin.

  通过合理的光化学途径，以消旋形式合成了绿色海洋颜料即去氧骨蛋白的二甲基酯。该生物活性颜料的两个丙酸酯残基已以差异化形式合成引入，这为合成天然存在的bone骨氨基酸衍生物开辟了道路。