(1R,1'R)-cis-[3-(1'-hydroxyethyl)-2,2-dimethylcyclobutyl]acetic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,1'R)-cis-[3-(1'-hydroxyethyl)-2,2-dimethylcyclobutyl]acetic acid
• 英文别名: (1R,1'R)-cis-pinolic acid；2-[(1R,3R)-3-[(1R)-1-hydroxyethyl]-2,2-dimethylcyclobutyl]acetic acid
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: JYNRDUMRXYBIKG-PRJMDXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid 在 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 6.5h， 生成 (1R,1'S)-cis-[3-(1'-hydroxyethyl)-2,2-dimethylcyclobutyl]acetic acid 、 (1R,1'R)-cis-[3-(1'-hydroxyethyl)-2,2-dimethylcyclobutyl]acetic acid
  参考文献：
  名称：

  Synthesis of two enantiomerically pure precursors of cyclobutane carbocyclic nucleosides

  摘要：

  Several bi-functionallized derivatives of cyclobutane have been synthesized by functional-group manipulation starting from (-)-cis-pinonic acid as a common precursor, the configuration of the pre-existing and newly formed stereogenic centers being determined by the configuration of the starting material, commercially available (-)-1S-alpha-pinene. Final products, (+)-(1S,1'R)-cis-1-[3'-(aminomethyl)-2',2'-dimethylcyclobutyl]ethanol 5 and (+)-(1S,1'R)-cis-1-[3'-(2"-aminoethyl)-2',2'-dimethylcyclobutyl]ethanol 6 are useful as precursors to cyclobutane carbocyclic nucleosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.033