(-)-N-(2-chloroethyl)-8,9-dibromonorapomorphine hydrochloride | 89849-67-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (-)-N-(2-chloroethyl)-8,9-dibromonorapomorphine hydrochloride
• CAS: 89849-67-2
• 化学式: C₁₈H₁₆Br₂ClNO₂*ClH
• 分子量: 510.052
• InChiKey: PLWNXHGNXSRZNZ-UTONKHPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.7
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-(2-hydroxyethyl)norapomorphine hydrochloride 在 palladium on activated charcoal 、 氯化亚砜 、 氢气 、 溴 、 三氟乙酸 作用下， 以 三氟乙酸 为溶剂， 反应 1.5h， 生成 (-)-N-(2-chloroethyl)-8,9-dibromonorapomorphine hydrochloride
  参考文献：
  名称：

  Aporphines. 58. N-(2-Chloroethyl)[8,9-2H]norapomorphine, an irreversible ligand for dopamine receptors: synthesis and application

  摘要：

  The synthesis of the title compounds (1c and its 2H isomer 1b) from N-(2-hydroxyethyl)norapomorphine was carried out by ring bromination, followed by chlorination to the 2-chloroethyl compound 6. Further reduction with 2H2 or 3H2 and Pd/C gave 1b or 1c. Radiochemically pure (97%) 1c was obtained with a specific activity of 16.3 Ci/mmol. The purity of 1c was determined by LC, HPLC, UV, and NMR. [3H]NCA was shown to label the D2 receptor; however, the D2 signal appears to be only a small portion of the total signal, which may include binding to other dopamine receptor subtypes (D1 and D3).

  DOI：

  10.1021/jm00372a019