(+/-)-dibromophakellin hydrochloride | 80923-89-3

• 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: (+/-)-dibromophakellin hydrochloride
• 英文别名: (1R,5S)-3-amino-7,8-dibromo-2,4,6,12-tetrazatetracyclo[10.3.0.01,5.06,10]pentadeca-3,7,9-trien-11-one;hydrochloride
• CAS: 80923-89-3
• 化学式: C₁₁H₁₁Br₂N₅O*ClH
• 分子量: 425.51
• InChiKey: ZKQQBCUDRQHYIY-QLSWKGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75.6
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,5S)-7,8-dibromo-3-ethoxy-2,4,6,12-tetrazatetracyclo[10.3.0.01,5.06,10]pentadeca-3,7,9-trien-11-one 在 丙酸铵 作用下， 反应 0.5h， 以45%的产率得到(+/-)-dibromophakellin hydrochloride
  参考文献：
  名称：

  Extending Pummerer Reaction Chemistry. Synthesis Studies in the Phakellin Alkaloid Area

  摘要：

  [GRAPHICS]The syntheses of (+/-)-dibromophakellstatin and, from this species, (+/-)-dibromophakellin are described. Oxidative cyclization of a phenylthiolated dihydrooroidin derivative triggered by a Pummerer reaction constitutes the key step in this biomimetic approach to this family of marine alkaloids.

  DOI：

  10.1021/jo701487j

文献信息

• Improved Conversion of Dihydrooroidin to Oroidin and Ugibohlin
  作者：Rareş-Petru Moldovan、Thomas Lindel

  DOI：10.1515/znb-2009-11-1247

  日期：2009.12.1

  Dihydrooroidin was converted to the marine natural product oroidin in 75% overall yield by chlorination of the 2-aminoimidazole unit in DMF, followed by dehydrochlorination. The natural product ugibohlin was synthesized for the first time by ring opening of dibromoisophakellin, which was obtained in a quantitative manner by heating the free base of dibromophakellin in neutral aqueous solution

  二氢海绵素在DMF中通过2-氨基咪唑单元的氯化和脱氢氯化反应，以75%的总产率转化为海洋天然产物海绵素。通过环开放反应合成了天然产物乌吉伯林，首次通过在中性水溶液中加热二溴异帕克林的游离碱，定量得到了二溴异帕克林。
• Extending Pummerer Reaction Chemistry. Synthesis Studies in the Phakellin Alkaloid Area
  作者：Ken S. Feldman、Amanda P. Skoumbourdis、Matthew D. Fodor

  DOI：10.1021/jo701487j

  日期：2007.10.1

  [GRAPHICS]The syntheses of (+/-)-dibromophakellstatin and, from this species, (+/-)-dibromophakellin are described. Oxidative cyclization of a phenylthiolated dihydrooroidin derivative triggered by a Pummerer reaction constitutes the key step in this biomimetic approach to this family of marine alkaloids.