| 595581-09-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• CAS: 595581-09-2
• 化学式: C₁₂H₁₉Br
• 分子量: 243.187
• InChiKey: ZPBMSYYXXLCOQR-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 38.0h， 生成 (2aRS,5aSR,8bRS)-8-hexyl-8b-methyl-1,2,2a,3,5,5a,7,8b-octahydro-4,6-dioxaacenaphthylene-1,7-dione
  参考文献：
  名称：

  A New Co₂(CO)₈-Mediated Tandem [5 + 1]/[2 + 2 + 1]-Cycloaddition Reaction:  A One-Pot Synthesis of Tricyclic δ-Lactones from cis-Epoxy Ene-ynes

  摘要：

  In the presence of Co2(CO)8 and CO, cis-epoxyalkynes bearing a tether olefin undergo a tandem [5 + 1]/[2 + 2 + 1]-cycloaddition to give tricyclic delta-lactones efficiently in a one-pot operation. The reaction mechanism is proposed to involve a cobalt-coordinated cyclic allene species.

  DOI：

  10.1021/ja0346633
• 作为产物：
  描述：

  (Z)-3-methylundec-2-en-4-yn-1-ol 在 三苯基膦 作用下， 以89%的产率得到
  参考文献：
  名称：

  A New Co₂(CO)₈-Mediated Tandem [5 + 1]/[2 + 2 + 1]-Cycloaddition Reaction:  A One-Pot Synthesis of Tricyclic δ-Lactones from cis-Epoxy Ene-ynes

  摘要：

  In the presence of Co2(CO)8 and CO, cis-epoxyalkynes bearing a tether olefin undergo a tandem [5 + 1]/[2 + 2 + 1]-cycloaddition to give tricyclic delta-lactones efficiently in a one-pot operation. The reaction mechanism is proposed to involve a cobalt-coordinated cyclic allene species.

  DOI：

  10.1021/ja0346633

文献信息

• Dicobaltoctacarbonyl-Mediated Synthesis of Tricyclic 5,6-Diydropyran-2-one Derivatives via Tandem Cycloaddition Reaction between <i>cis</i>-Epoxyalkynes, a Tethered Olefin, and Carbon Monoxide
  作者：Arjan Odedra、Shie-Fu Lush、Rai-Shung Liu

  DOI：10.1021/jo0620617

  日期：2007.1.1

  [GRAPHIC]Cobalt carbonyl complex Co-2(CO)(8) implemented an intramolecular carbonylation of cis-epoxyalkynes to generate Co-2(CO)(6)-stabilized gamma-lactonyl allene species. For 1,1,2-trisubstituted epoxyalkynes, this Co-2(CO)(6)-allene species reacted with a tethered olefin to give [2 + 2]-cycloadducts, and with CO and a tethered olefin to produce [2 + 2 + 1]-cycloadducts. These resulting cycloadducts have a 5,6-diydropyran-2-one core fused with a cyclobutane and a cyclopentanone ring, respectively. For 1,2-disubstituted cis-epoxyalkyne and 1,1,2-trisubstituted cis-epoxyalkynes bearing a heteroatom constituent, cyclization of the corresponding epoxyalkyne with a tethered alkene is invariably accompanied by incorporation of CO to produce a [2 + 2 + 1]-cycloadduct, even in the absence of CO. We have prepared various 1,1,2-trisubstituted and 1,2-disubstituted cis-epoxyalkynes to generalize such cycloaddition pathways. Attempt to use an organic promoter to perform these tandem cycloadditions was unsuccessful because of a competing Pauson-Khand reaction. Cyclization of a 1,2-disubstituted epoxyalkyne with a tethered diene was achieved successfully in one case, but the yield was low (25%).