(1R,1'S)-cis-[3-(1'-hydroxyethyl)-2,2-dimethylcyclobutyl]acetic acid | 377755-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,1'S)-cis-[3-(1'-hydroxyethyl)-2,2-dimethylcyclobutyl]acetic acid
• 英文别名: pinolic acid；(1R,1'S)-cis-pinolic acid；2-[(1R,3R)-3-[(1S)-1-hydroxyethyl]-2,2-dimethylcyclobutyl]acetic acid
• CAS: 377755-43-6
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: JYNRDUMRXYBIKG-RNJXMRFFSA-N

物化性质

• 熔点：
  120-121 °C(Solv: water (7732-18-5))
• 沸点：
  310.8±15.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (1R,1'S)-cis-[3-(1'-hydroxyethyl)-2,2-dimethylcyclobutyl]acetic acid 在 吡啶 、 氯甲酸乙酯 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 (1S,1'S)-cis-3-(1'-acetoxyethyl)-2,2-dimethylcyclobutylmethyl isocyanate
  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
• 作为产物：
  描述：

  (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以95%的产率得到(1R,1'S)-cis-[3-(1'-hydroxyethyl)-2,2-dimethylcyclobutyl]acetic acid
  参考文献：
  名称：

  修饰的环戊烷碳核苷：其抗病毒活性的合成和评估

  摘要：

  本文介绍了从1S-α-pine烯合成一些9-（2-环丁基乙基）鸟嘌呤衍生物和类似碳核苷的方法。当在进行的抗病毒试验中进行测定时，它们均未显示出可检测的选择性。

  DOI：

  10.1081/ncn-100002504

文献信息

• MODIFIED CYCLOBUTANE CARBONUCLEOSIDES: SYNTHESIS AND EVALUATION OF THEIR ANTIVIRAL ACTIVITY
  作者：F. Fernández、A. R. Hergueta、C. López、E. De Clercq、J. Balzarini

  DOI：10.1081/ncn-100002504

  日期：2001.3.31

  The synthesis of some 9-(2-cyclobutylethyl)guanine derivatives and analogous carbonucleosides from 1S-α-pinene is here presented. None of them showed detectable selectivity when assayed in the performed anti-viral tests.

  本文介绍了从1S-α-pine烯合成一些9-（2-环丁基乙基）鸟嘌呤衍生物和类似碳核苷的方法。当在进行的抗病毒试验中进行测定时，它们均未显示出可检测的选择性。
• Synthesis of two enantiomerically pure precursors of cyclobutane carbocyclic nucleosides
  作者：Antonio R. Hergueta、Carmen López、Franco Fernández、Olga Caamaño、José M. Blanco

  DOI：10.1016/j.tetasy.2003.09.033

  日期：2003.11

  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.