ethyl 3,5-dimethyl-4-(hydroxyethyl)-1H-pyrrole-2-carboxylate | 161926-26-7

• 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 3,5-dimethyl-4-(hydroxyethyl)-1H-pyrrole-2-carboxylate
• 英文别名: 3,5-dimethyl-2-ethoxycarbonyl-4-(2-hydroxyethyl)-1H-pyrrole；ethyl 4-(2-hydroxyethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 161926-26-7
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: GWDGFFBAKPXUOO-UHFFFAOYSA-N

物化性质

• 熔点：
  100.5 °C
• 沸点：
  366.6±42.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3,5-dimethyl-4-(hydroxyethyl)-1H-pyrrole-2-carboxylate 在 三乙胺 、 sodium bromide 、 sodium sulfite 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 25.0h， 生成 ethyl 3,5-dimethyl-4-(2-ethanesulfonic acid sodium salt)-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
• 作为产物：
  描述：

  3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole-4-acetic acid ethyl ester 在 sodium hydroxide 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 51.0h， 生成 ethyl 3,5-dimethyl-4-(hydroxyethyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  13种CO 2 H标记的单和双吡咯羧酸的合成和酸度常数。来自13 C-NMR的pK a

  摘要：

  制备了六种在CO 2 H基团中高度富集13 C的单羧酸，并在H 2 O和H 2 O-（CD 3）2中以低浓度10 -4 -10 -5 M的pK a值进行了测定。通过分析pH依赖性13 CO 2 H NMR化学位移分析SO混合物。CO的变化的曲线图2 H（CO 2 - ）13 C-NMR化学位移VS pH值，得到一个典型的滴定曲线从其中的pK一个的对[1- 13C] -phenylpropionic（1）和[1- 13 C] -phenylacetic（2测定）的酸为4.60和H中分别4.16 2 O，和4.67和4.31分别H中2 -O-27％（体积）（CD 3）2 SO。经测定，在H 2 O-27％vol（CD 3）2 SO中，胆红素类似物，黄胆红酸（5）和去黄胆红酸（6）的pK a值分别为4.76和4.64 ，并推断为pK a值〜 H 2 O中为4.62和4.51 。

  DOI：

  10.1016/0040-4020(94)01052-2

文献信息

• Synthesis and acidity constants of 13CO2H-labelled mono and dipyrrole carboxylic acids. pKa from 13C-NMR
  作者：Darren L. Holmes、David A. Lightner

  DOI：10.1016/0040-4020(94)01052-2

  日期：1995.2

  [1-13C]-phenylacetic (2) acids were determined to be 4.60 and 4.16 respectively in H2O, and 4.67 and 4.31 respectively in H2O-27% vol (CD3)2SO. Bilirubin analogs, xanthobilirubic acid (5) and nor-xanthobilirubic acid (6) were determined to have pKa values of 4.76 and 4.64 respectively in H2O-27% vol (CD3)2SO, and extrapolated to pKa values ∼4.62 and 4.51 in H2O.

  制备了六种在CO 2 H基团中高度富集13 C的单羧酸，并在H 2 O和H 2 O-（CD 3）2中以低浓度10 -4 -10 -5 M的pK a值进行了测定。通过分析pH依赖性13 CO 2 H NMR化学位移分析SO混合物。CO的变化的曲线图2 H（CO 2 - ）13 C-NMR化学位移VS pH值，得到一个典型的滴定曲线从其中的pK一个的对[1- 13C] -phenylpropionic（1）和[1- 13 C] -phenylacetic（2测定）的酸为4.60和H中分别4.16 2 O，和4.67和4.31分别H中2 -O-27％（体积）（CD 3）2 SO。经测定，在H 2 O-27％vol（CD 3）2 SO中，胆红素类似物，黄胆红酸（5）和去黄胆红酸（6）的pK a值分别为4.76和4.64 ，并推断为pK a值〜 H 2 O中为4.62和4.51 。
• 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.