(4Z)-14-tert-butoxycarbonyl-10,17-dihydro-3,13-dimethyl-12-(2-methoxycarbonylethyl)-2,7,8-triethyl-tripyrrin-1(15H)-one | 226223-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (4Z)-14-tert-butoxycarbonyl-10,17-dihydro-3,13-dimethyl-12-(2-methoxycarbonylethyl)-2,7,8-triethyl-tripyrrin-1(15H)-one
• 英文别名: tert-butyl 5-[[3,4-diethyl-5-[(Z)-(4-ethyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl]methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylate
• CAS: 226223-28-5
• 化学式: C₃₁H₄₃N₃O₅
• 分子量: 537.7
• InChiKey: DFDCJTOAXBWWAY-HAHDFKILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4Z)-14-tert-butoxycarbonyl-10,17-dihydro-3,13-dimethyl-12-(2-methoxycarbonylethyl)-2,7,8-triethyl-tripyrrin-1(15H)-one 在 sodium hydroxide 、 维生素 C 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以64%的产率得到(4Z)-14-tert-butoxycarbonyl-12-(2-carboxyethyl)-10,17-dihydro-3,13-dimethyl-2,7,8-triethyl-tripyrrin-1(15H)-one
  参考文献：
  名称：

  An Intramolecularly Hydrogen Bonded Dihydrotripyrrinone

  摘要：

  A yellow tripyrrole analog (1) of bilirubin has been synthesized, and its lone propionic acid group is found to engage in conformation determining, intramolecular hydrogen bonding in solution and in the crystal. Molecular modelling and X-ray crystallography reveal an abbreviated ridge-tile or L-shape conformation in which an essentially planar dipyninone is hydrogen bonded to the single opposing propionic acid group. In the (arbitrary) (P)-helicity ridge-tile, the torsion angles about C(10) are computed to be 55 degrees and 61 degrees by molecular dynamics and found to be 66 degrees and 53 degrees in the crystal. Such torsion angles lead to an interplanar dihedral angle (similar to 93 degrees) between the dipyninone and its adjoining pyrrole that is very close to the dihedral angle (similar to 98 degrees) found in intramolecularly hydrogen bonded bilirubin.

  DOI：

  10.1007/pl00010223
• 作为产物：
  描述：

  3,4-二乙基-5-甲基-2-吡咯羧酸乙酯 在 氢氧化钾 、 ammonium cerium(IV) nitrate 、 potassium acetate 、 sodium acetate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 6.33h， 生成 (4Z)-14-tert-butoxycarbonyl-10,17-dihydro-3,13-dimethyl-12-(2-methoxycarbonylethyl)-2,7,8-triethyl-tripyrrin-1(15H)-one
  参考文献：
  名称：

  An Intramolecularly Hydrogen Bonded Dihydrotripyrrinone

  摘要：

  A yellow tripyrrole analog (1) of bilirubin has been synthesized, and its lone propionic acid group is found to engage in conformation determining, intramolecular hydrogen bonding in solution and in the crystal. Molecular modelling and X-ray crystallography reveal an abbreviated ridge-tile or L-shape conformation in which an essentially planar dipyninone is hydrogen bonded to the single opposing propionic acid group. In the (arbitrary) (P)-helicity ridge-tile, the torsion angles about C(10) are computed to be 55 degrees and 61 degrees by molecular dynamics and found to be 66 degrees and 53 degrees in the crystal. Such torsion angles lead to an interplanar dihedral angle (similar to 93 degrees) between the dipyninone and its adjoining pyrrole that is very close to the dihedral angle (similar to 98 degrees) found in intramolecularly hydrogen bonded bilirubin.

  DOI：

  10.1007/pl00010223

文献信息

• An Intramolecularly Hydrogen Bonded Dihydrotripyrrinone
  作者：Adrianne K. Tipton、David A. Lightner

  DOI：10.1007/pl00010223

  日期：1999.3

  A yellow tripyrrole analog (1) of bilirubin has been synthesized, and its lone propionic acid group is found to engage in conformation determining, intramolecular hydrogen bonding in solution and in the crystal. Molecular modelling and X-ray crystallography reveal an abbreviated ridge-tile or L-shape conformation in which an essentially planar dipyninone is hydrogen bonded to the single opposing propionic acid group. In the (arbitrary) (P)-helicity ridge-tile, the torsion angles about C(10) are computed to be 55 degrees and 61 degrees by molecular dynamics and found to be 66 degrees and 53 degrees in the crystal. Such torsion angles lead to an interplanar dihedral angle (similar to 93 degrees) between the dipyninone and its adjoining pyrrole that is very close to the dihedral angle (similar to 98 degrees) found in intramolecularly hydrogen bonded bilirubin.