ethyl 4-(2-bromoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate | 402565-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 4-(2-bromoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 402565-01-9
• 化学式: C₁₁H₁₆BrNO₂
• 分子量: 274.158
• InChiKey: GCTOTNAGGFGTLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 4-(2-bromoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate 在 sodium hydroxide 、 sodium sulfite 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 12.5h， 生成 3,5-dimethyl-4-(2-ethanesulfonic acid sodium salt)-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  A Water-Soluble Synthetic Bilirubin with Carboxyl Groups Replaced by Sulfonyl Moieties

  摘要：

  The first symmetrical bilirubin analog with CO2H groups replaced by SO3H, 8,12-bis-(2-sulfo-ethyl)-3,17-diethyl-2,7,13,18-tetramethyl-(10H,21H,23H,24H)-bilin-1,19-dione, was synthesized from methyl (2,4-dimethyl-5-ethoxycarbonyl-1H-pyrrol-3-yl) acetate in nine steps via the sulfonic acid analog of xanthobilirubic acid (XBR) and isolated as its disodium salt. The sulfonic acid group was introduced at an early stage of the synthesis by reaction of an intermediate, ethyl 4-(2-bromoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate, with sodium sulfite. The disodium bilirubin disulfonate exhibits NMR spectroscopic properties rather similar to those of the parent carboxylic acid, mesobilirubin-XIII alpha; however, its UV/Vis spectra are blue-shifted and broadened relative to those of the parent compound. Like mesobilirubin, the disulfonate displays-a positive exciton chirality circular dichroism spectrum, albeit with weaker Cotton effects, in a buffered aqueous solution (pH = 7.4) containing a 2:1 molar ratio of human serum albumin.

  DOI：

  10.1007/s007060170035
• 作为产物：
  描述：

  ethyl 4<(methoxycarbonyl)methyl>-3,5-dimethylpyrrole-2-carboxylate 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 三乙胺 、 sodium bromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 40.0h， 生成 ethyl 4-(2-bromoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  A Water-Soluble Synthetic Bilirubin with Carboxyl Groups Replaced by Sulfonyl Moieties

  摘要：

  The first symmetrical bilirubin analog with CO2H groups replaced by SO3H, 8,12-bis-(2-sulfo-ethyl)-3,17-diethyl-2,7,13,18-tetramethyl-(10H,21H,23H,24H)-bilin-1,19-dione, was synthesized from methyl (2,4-dimethyl-5-ethoxycarbonyl-1H-pyrrol-3-yl) acetate in nine steps via the sulfonic acid analog of xanthobilirubic acid (XBR) and isolated as its disodium salt. The sulfonic acid group was introduced at an early stage of the synthesis by reaction of an intermediate, ethyl 4-(2-bromoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate, with sodium sulfite. The disodium bilirubin disulfonate exhibits NMR spectroscopic properties rather similar to those of the parent carboxylic acid, mesobilirubin-XIII alpha; however, its UV/Vis spectra are blue-shifted and broadened relative to those of the parent compound. Like mesobilirubin, the disulfonate displays-a positive exciton chirality circular dichroism spectrum, albeit with weaker Cotton effects, in a buffered aqueous solution (pH = 7.4) containing a 2:1 molar ratio of human serum albumin.

  DOI：

  10.1007/s007060170035

文献信息

• A Water-Soluble Synthetic Bilirubin with Carboxyl Groups Replaced by Sulfonyl Moieties
  作者：Stefan E. Boiadjiev、David A. Lightner

  DOI：10.1007/s007060170035

  日期：2001.10

  The first symmetrical bilirubin analog with CO2H groups replaced by SO3H, 8,12-bis-(2-sulfo-ethyl)-3,17-diethyl-2,7,13,18-tetramethyl-(10H,21H,23H,24H)-bilin-1,19-dione, was synthesized from methyl (2,4-dimethyl-5-ethoxycarbonyl-1H-pyrrol-3-yl) acetate in nine steps via the sulfonic acid analog of xanthobilirubic acid (XBR) and isolated as its disodium salt. The sulfonic acid group was introduced at an early stage of the synthesis by reaction of an intermediate, ethyl 4-(2-bromoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate, with sodium sulfite. The disodium bilirubin disulfonate exhibits NMR spectroscopic properties rather similar to those of the parent carboxylic acid, mesobilirubin-XIII alpha; however, its UV/Vis spectra are blue-shifted and broadened relative to those of the parent compound. Like mesobilirubin, the disulfonate displays-a positive exciton chirality circular dichroism spectrum, albeit with weaker Cotton effects, in a buffered aqueous solution (pH = 7.4) containing a 2:1 molar ratio of human serum albumin.