1-[1-((S)-1-Hydroxy-but-3-enyl)-cyclopropyl]-propan-1-one | 202333-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[1-((S)-1-Hydroxy-but-3-enyl)-cyclopropyl]-propan-1-one
• CAS: 202333-67-3
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: LNFWHQFPAPBOAQ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 1-[1-((S)-1-Hydroxy-but-3-enyl)-cyclopropyl]-propan-1-one 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成 1-{1-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-cyclopropyl}-propan-1-one
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach

  摘要：

  AbstractFor structure‐activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem‐dimethyl group at position C‐4 (4,4‐ethano‐epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7–9 for the oxazole series (compounds 2, 14–18, 21–26) and building blocks 8, 30, and 31 for the 4,4‐ethano series (compounds 3,39–43, 46–51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)‐(PCy3)2], and d) epoxidation of the macrocycle double bond.

  DOI：

  10.1002/chem.19970031211
• 作为产物：
  描述：

  1-[1-(Hydroxymethyl)cyclopropyl]propan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 (-)-B-methoxydiisopinocampheylborane 作用下， 反应 3.75h， 生成 1-[1-((S)-1-Hydroxy-but-3-enyl)-cyclopropyl]-propan-1-one
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach

  摘要：

  AbstractFor structure‐activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem‐dimethyl group at position C‐4 (4,4‐ethano‐epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7–9 for the oxazole series (compounds 2, 14–18, 21–26) and building blocks 8, 30, and 31 for the 4,4‐ethano series (compounds 3,39–43, 46–51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)‐(PCy3)2], and d) epoxidation of the macrocycle double bond.

  DOI：

  10.1002/chem.19970031211