(1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanone hydrochloride | 147780-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanone hydrochloride
• 英文别名: (1S,3R)-1-Amino-3-(hydroxymethyl)cyclopentane hydrochloride；[(1R,3S)-3-Aminocyclopentyl]methanol hydrochloride；[(1R,3S)-3-aminocyclopentyl]methanol;hydrochloride
• CAS: 147780-38-9
• 化学式: C₆H₁₃NO*ClH
• 分子量: 151.636
• InChiKey: QXSRCFAPVVTLBT-IBTYICNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,4R)-N-(9-Phenylfluoren-9-yl)-2-azabicyclo<2.2.1>heptan-3-one 在 盐酸 、 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 39.0h， 生成 (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanone hydrochloride
  参考文献：
  名称：

  Chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane, precursor for carbocyclic nucleoside synthesis. Dieckmann cyclization with an .alpha.-amino acid

  摘要：

  Carbocyclic nucleosides are important isosteres of nucleosides possessing a variety of antiviral and antineoplastic activities. We report here a new method for the chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane. This compound is a key precursor for the synthesis of some carbocyclic nucleosides. The method involves (1) an improved synthesis of (S)-2-aminoadipic acid; (2) Dieckmann cyclization of this alpha-amino acid to an aminocyclopentanone; and (3) elaboration of the latter to the target (1S,3R)-l-amino-3-(hydroxymethyl)cyclopentane. The starting (S)-2-aminoadipic acid delta-methyl ester was prepared enantiomerically pure from (S)-aspartic acid in 51% overall yield. Dieckmann condensation converted this amino acid to a (methoxycarbonyl)-cyclopentanone, and reduction of the ketone followed by elimination yielded (S)-3-[N-(9-phenylfluoren-9-yl)amino]-1-(methoxycarbonyl)cyclopentene. Reduction of the double bond gave a mixture of the cis and trans diastereomers. This mixture was converted to a single diastereomer by epimerization and trapping of the cis isomer as (1S,4R)-2-(9-phenylfluoren-9-yl)-2-azabicyclo[2.2.1]heptan-3-one. Hydrolytic cleavage of the lactam followed by reduction gave (IS,3R)-1-amino-3-(hydroxymethyl)-cyclopentane.

  DOI：

  10.1021/jo00061a006