(1S,1'S)-cis-3-(1'-acetoxyethyl)-2,2-dimethylcyclobutylmethyl isocyanate | 649760-29-2

• 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: (1S,1'S)-cis-3-(1'-acetoxyethyl)-2,2-dimethylcyclobutylmethyl isocyanate
• CAS: 649760-29-2
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: HAYYBZVBKAOMCH-GDPRMGEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 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：
  55.73
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,1'S)-cis-3-(1'-acetoxyethyl)-2,2-dimethylcyclobutylmethyl isocyanate 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 水 、 甲苯 、 正丁醇 为溶剂， 反应 108.0h， 生成 (+)-(1S,1'R)-cis-1-[3'-(5-amino-6-chloropyrimidin-4-ylaminomethyl)-2',2'-dimethylcyclobutyl]ethanol
  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：

  (1R,1'S)-cis-[3-(1'-acetoxyethyl)-2,2-dimethylcyclobutyl]acetic acid 在 氯甲酸乙酯 、 三乙胺 、 sodium azide 作用下， 以 丙酮 、 水 、 甲苯 为溶剂， 反应 2.0h， 以77%的产率得到(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