prop-2-enyl 4-bromo-1H-pyrrole-2-carboxylate | 1312441-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: prop-2-enyl 4-bromo-1H-pyrrole-2-carboxylate
• CAS: 1312441-59-0
• 化学式: C₈H₈BrNO₂
• 分子量: 230.061
• InChiKey: JUWWDSYMRULHBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  吡咯-2-羧酸 在 吡啶 、 氯化亚砜 、 Ascophyllum nodosum vanadate(V)-dependent bromoperoxidase I 、 双氧水 、 sodium bromide 作用下， 以 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 74.33h， 生成 prop-2-enyl 4-bromo-1H-pyrrole-2-carboxylate 、 prop-2-enyl 4,5-dibromo-1H-pyrrole-2-carboxylate 、 prop-2-enyl 3,4,5-tribromo-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Parameters for bromination of pyrroles in bromoperoxidase-catalyzed oxidations

  摘要：

  Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 degrees C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 mu mol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4-ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2-carboxamide (from Acanthella carteri). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.010

文献信息

• Parameters for bromination of pyrroles in bromoperoxidase-catalyzed oxidations
  作者：Diana Wischang、Jens Hartung

  DOI：10.1016/j.tet.2011.04.010

  日期：2011.6

  Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 degrees C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 mu mol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4-ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2-carboxamide (from Acanthella carteri). (C) 2011 Elsevier Ltd. All rights reserved.