(2S)-{[(1R)-2-hydroxy-1-phenylethyl]amino}[3-(trifluoromethyl)bicyclo[1.1.1]pent-1-yl]acetic acid | 1220115-45-6

• 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: (2S)-{[(1R)-2-hydroxy-1-phenylethyl]amino}[3-(trifluoromethyl)bicyclo[1.1.1]pent-1-yl]acetic acid
• CAS: 1220115-45-6
• 化学式: C₁₆H₁₈F₃NO₃
• 分子量: 329.319
• InChiKey: HGNQSKWLOLWCJB-CZWNDGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  69.56
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (2S)-2-{[(1R)-2-hydroxy-1-phenylethyl]amino}-2-[3-(trifluoromethyl)bicyclo[1.1.1]pent-1-yl]acetonitrile 在 盐酸 作用下， 反应 2.0h， 以70%的产率得到(2S)-2-amino-2-[3-(trifluoromethyl)bicyclo[1.1.1]pent-1-yl]ethanoic acid
  参考文献：
  名称：

  An optimized protocol for the multigram synthesis of 3-(trifluoromethyl)bicyclo[1.1.1]pent-1-ylglycine (CF3-Bpg)

  摘要：

  An optimized procedure for the multigram synthesis of 3-(trifluoromethyl)bicyclo[1.1.1]pent-1-ylglycine (CF3-Bpg) has been developed. The overall yield of the synthesis for the optimized up-scaling was increased from 35% to 53%. Moreover, conditions for separating the key isomeric aminonitriles 7 and 8 by crystallization were found, which greatly facilitated the isolation of 8 on a multigram scale. Following this optimized protocol, 100 g of optically pure CF3-Bpg have been synthesized. Crown Copyright (C) 2009 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.10.004