(1R)-1-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]-4-prop-2-enoxybut-2-yn-1-ol | 1107622-72-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R)-1-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]-4-prop-2-enoxybut-2-yn-1-ol
• CAS: 1107622-72-9
• 化学式: C₁₆H₂₈O₄Si
• 分子量: 312.481
• InChiKey: UBHDIJZOKXWEQA-KFWWJZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]-4-prop-2-enoxybut-2-yn-1-ol 在 喹啉 、 5 wt% palladium on calcium carbonate 、 氢气 、 lead(IV) tetraacetate 作用下， 以 正己烷 、 乙酸乙酯 为溶剂， 以83%的产率得到
  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 borane-dimethyl sulfide complex 、 (R)-CBS 作用下， 以 四氢呋喃 为溶剂， 反应 4.08h， 以73%的产率得到
  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.