(1R,2R)-tert-butyl 2-((R)-5-(benzyloxy)-1-hydroxypentyl)cyclopropanecarboxylate | 1035930-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R)-tert-butyl 2-((R)-5-(benzyloxy)-1-hydroxypentyl)cyclopropanecarboxylate
• 英文别名: tert-butyl (1R,2R)-2-[(1R)-1-hydroxy-5-phenylmethoxypentyl]cyclopropane-1-carboxylate
• CAS: 1035930-87-0
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: CDTQWCIQUGNFBG-KZNAEPCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-tert-butyl 2-((R)-5-(benzyloxy)-1-hydroxypentyl)cyclopropanecarboxylate 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1R,2R)-tert-butyl 2-((R)-5-(benzyloxy)-1-(triethylsilyloxy)pentyl)cyclopropanecarboxylate
  参考文献：
  名称：

  Enantioselective Total Synthesis of Eicosanoid and Its Congener, Using Organocatalytic Cyclopropanation, and Catalytic Asymmetric Transfer Hydrogenation Reactions as Key Steps

  摘要：

  An enantioselective unified strategy for the syntheses of the oxylipin class of natural products was accomplished. Our strategy relies on three catalytic steps: (a) organocatalytic cyclopropanation, (b) the catalytic asymmetric transfer hydrogenation (CATHy) reaction, and (c) the Nozaki-Hiyama-Kishi reaction.

  DOI：

  10.1021/jo800631z
• 作为产物：
  描述：

  (1R,2R)-tert-butyl 2-(5-(benzyloxy)pentanoyl)cyclopropane carboxylate 在 (S,S)-1,2-diphenylethylenediamine-based ruthenium complex 氢氧化钾 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 6.0h， 以65%的产率得到(1R,2R)-tert-butyl 2-((S)-5-(benzyloxy)-1-hydroxypentyl)cyclopropanecarboxylate
  参考文献：
  名称：

  Enantioselective Total Synthesis of Eicosanoid and Its Congener, Using Organocatalytic Cyclopropanation, and Catalytic Asymmetric Transfer Hydrogenation Reactions as Key Steps

  摘要：

  An enantioselective unified strategy for the syntheses of the oxylipin class of natural products was accomplished. Our strategy relies on three catalytic steps: (a) organocatalytic cyclopropanation, (b) the catalytic asymmetric transfer hydrogenation (CATHy) reaction, and (c) the Nozaki-Hiyama-Kishi reaction.

  DOI：

  10.1021/jo800631z