(4R,5R)-5,6-(isopropylidenedioxy)-4-(pivaloyloxy)-1-(trimethylsilyl)hex-1-yne | 1006369-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-5,6-(isopropylidenedioxy)-4-(pivaloyloxy)-1-(trimethylsilyl)hex-1-yne
• 英文别名: [(1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-trimethylsilylbut-3-ynyl] 2,2-dimethylpropanoate
• CAS: 1006369-80-7
• 化学式: C₁₇H₃₀O₄Si
• 分子量: 326.508
• InChiKey: STOOBMDLWARTNI-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5,6-(isopropylidenedioxy)-4-(pivaloyloxy)-1-(trimethylsilyl)hex-1-yne 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 乙腈 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction

  摘要：

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.

  DOI：

  10.1021/jo702330y
• 作为产物：
  描述：

  、 三甲基乙酰氯 以 吡啶 为溶剂， 反应 20.0h， 以214 mg的产率得到(4R,5R)-5,6-(isopropylidenedioxy)-4-(pivaloyloxy)-1-(trimethylsilyl)hex-1-yne
  参考文献：
  名称：

  Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction

  摘要：

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.

  DOI：

  10.1021/jo702330y