(4R)-5-azido-4-hydroxy-1-(trimethylsilyl)pent-1-yne | 474671-00-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (4R)-5-azido-4-hydroxy-1-(trimethylsilyl)pent-1-yne
• 英文别名: (2R)-1-azido-5-trimethylsilylpent-4-yn-2-ol
• CAS: 474671-00-6
• 化学式: C₈H₁₅N₃OSi
• 分子量: 197.312
• InChiKey: FENKAYBRSOFDBR-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  68.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4R)-5-azido-4-hydroxy-1-(trimethylsilyl)pent-1-yne 在 正丁基锂 、 四丁基氟化铵 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.0h， 生成 (R)-2-Oxo-5-prop-2-ynyl-oxazolidine-3-carboxylic acid methyl-(2-nitro-benzyl)-amide
  参考文献：
  名称：

  Alkynyliodonium Salts in Organic Synthesis. Development of a Unified Strategy for the Syntheses of (−)-Agelastatin A and (−)-Agelastatin B

  摘要：

  The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium. salt --> alkylidenecarbene --> cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.

  DOI：

  10.1021/jo026287v
• 作为产物：
  描述：

  Trimethyl-((R)-3-oxiranyl-prop-1-ynyl)-silane 在 sodium azide 、 ammonium chloride 作用下， 以 乙醇 为溶剂， 反应 39.0h， 生成 (4R)-5-azido-4-hydroxy-1-(trimethylsilyl)pent-1-yne
  参考文献：
  名称：

  Alkynyliodonium Salts in Organic Synthesis. Development of a Unified Strategy for the Syntheses of (−)-Agelastatin A and (−)-Agelastatin B

  摘要：

  The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium. salt --> alkylidenecarbene --> cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.

  DOI：

  10.1021/jo026287v