(R)-RS-56812-14C

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-RS-56812-14C
• 英文别名: N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-2-(1-methylindol-3-yl)-2-oxoacetamide
• 化学式: C₁₈H₂₁N₃O₂
• 分子量: 313.373
• InChiKey: ZNAPADWWBWFMCQ-QNQYIDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-methylindole-3-glyoxylyl chloride 、 (R)-3-aminoquinuclidine-[3-14C] hydrochloride 在 lithium hydroxide 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以95%的产率得到(R)-RS-56812-14C
  参考文献：
  名称：

  Synthesis of (R) and (S) 3-aminoquinuclidine-[3-14C] enantiomers, important components of a variety of 5-HT3 ligands

  摘要：

  3-Aminoquinuclidine, an important fragment associated with many 5-HT (serotonin) receptor ligands, has been synthesized using a C-14- carbonation based sequence to prepare the starting material, isonicotinic C-14-acid (6). Elaboration of (6) to alpha-bromoacetyl-[C-14] isonipecotic acid (10) via the corresponding diazoketone, followed by intamolecular cyclization, gave the key intermediate 3-quinuclidone-[3-C-14] (3). 3-quinuclidone-[3-C-14] was converted to a mixture of phenethylamine diastereomers. Carrier free crystallization and hydrogenolysis furnished both (R) and (S) 3-aminoquinuclidine-[3-C-14] enantiomers at >99% optical purity.

  DOI：

  10.1002/(sici)1099-1344(199601)38:1<19::aid-jlcr805>3.0.co;2-d

文献信息

• Synthesis of (R) and (S) 3-aminoquinuclidine-[3-14C] enantiomers, important components of a variety of 5-HT3 ligands
  作者：Howard Parnes、Emma J. Shelton

  DOI：10.1002/(sici)1099-1344(199601)38:1<19::aid-jlcr805>3.0.co;2-d

  日期：1996.1

  3-Aminoquinuclidine, an important fragment associated with many 5-HT (serotonin) receptor ligands, has been synthesized using a C-14- carbonation based sequence to prepare the starting material, isonicotinic C-14-acid (6). Elaboration of (6) to alpha-bromoacetyl-[C-14] isonipecotic acid (10) via the corresponding diazoketone, followed by intamolecular cyclization, gave the key intermediate 3-quinuclidone-[3-C-14] (3). 3-quinuclidone-[3-C-14] was converted to a mixture of phenethylamine diastereomers. Carrier free crystallization and hydrogenolysis furnished both (R) and (S) 3-aminoquinuclidine-[3-C-14] enantiomers at >99% optical purity.