(1R,1'S)-cis-[3-(1'-acetoxyethyl)-2,2-dimethylcyclobutyl]acetic acid | 649760-28-1

• 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: (1R,1'S)-cis-[3-(1'-acetoxyethyl)-2,2-dimethylcyclobutyl]acetic acid
• CAS: 649760-28-1
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: ZXTPRQVUTYJQIB-SFGNSQDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,1'S)-cis-[3-(1'-acetoxyethyl)-2,2-dimethylcyclobutyl]acetic acid 在 吡啶 、 氢氧化钾 、 氯甲酸乙酯 、 三乙胺 作用下， 以 甲醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 56.0h， 生成 (1S,1'R)-cis-1-[3'-(acetamidomethyl)-2',2'-dimethylcyclobutyl]ethyl acetate
  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 吡啶 、 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 24.5h， 生成 (1R,1'S)-cis-[3-(1'-acetoxyethyl)-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