(1S,5R,6R)-3-(3-methylbut-3-en-1-ynyl)-5-tri(propan-2-yl)silyloxy-7-oxabicyclo[4.1.0]hept-3-en-2-one | 1107622-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5R,6R)-3-(3-methylbut-3-en-1-ynyl)-5-tri(propan-2-yl)silyloxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
• CAS: 1107622-82-1
• 化学式: C₂₀H₃₀O₃Si
• 分子量: 346.542
• InChiKey: LWTZEHJXLPTHMG-YZGWKJHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,5R,6R)-3-(3-methylbut-3-en-1-ynyl)-5-tri(propan-2-yl)silyloxy-7-oxabicyclo[4.1.0]hept-3-en-2-one 在 吡啶 、 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以81%的产率得到(1S,2R,6S)-2-羟基-4-(3-甲基丁-3-烯-1-炔基)-7-氧杂双环[4.1.0]庚-3-烯-5-酮
  参考文献：
  名称：

  Tandem Enyne Metathesis−Metallotropic [1,3]-Shift for a Concise Total Syntheses of (+)-Asperpentyn, (−)-Harveynone, and (−)-Tricholomenyn A

  摘要：

  A tandem reaction sequence involving relay metathesis-induced enyne RCM and metallotropic [1,3]-shift is an effective tool to construct cyclic alkenes with embedded 1,5-dien-3-yne moieties from acyclic precursors containing a 1,3-diyne. Total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A have been accomplished by implementing this metathesis-based tandem reaction sequence as the key step.

  DOI：

  10.1021/ol802675j
• 作为产物：
  描述：

  在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以93%的产率得到(1S,5R,6R)-3-(3-methylbut-3-en-1-ynyl)-5-tri(propan-2-yl)silyloxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
  参考文献：
  名称：

  Tandem Enyne Metathesis−Metallotropic [1,3]-Shift for a Concise Total Syntheses of (+)-Asperpentyn, (−)-Harveynone, and (−)-Tricholomenyn A

  摘要：

  A tandem reaction sequence involving relay metathesis-induced enyne RCM and metallotropic [1,3]-shift is an effective tool to construct cyclic alkenes with embedded 1,5-dien-3-yne moieties from acyclic precursors containing a 1,3-diyne. Total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A have been accomplished by implementing this metathesis-based tandem reaction sequence as the key step.

  DOI：

  10.1021/ol802675j

文献信息

• Tandem Enyne Metathesis−Metallotropic [1,3]-Shift for a Concise Total Syntheses of (+)-Asperpentyn, (−)-Harveynone, and (−)-Tricholomenyn A
  作者：Jingwei Li、Sangho Park、Reagan L. Miller、Daesung Lee

  DOI：10.1021/ol802675j

  日期：2009.2.5

  A tandem reaction sequence involving relay metathesis-induced enyne RCM and metallotropic [1,3]-shift is an effective tool to construct cyclic alkenes with embedded 1,5-dien-3-yne moieties from acyclic precursors containing a 1,3-diyne. Total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A have been accomplished by implementing this metathesis-based tandem reaction sequence as the key step.