2-tridec-4-en-6-ynyloxy-tetrahydro-pyran | 924889-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-tridec-4-en-6-ynyloxy-tetrahydro-pyran
• 英文别名: 2-[(Z)-tridec-4-en-6-ynoxy]oxane
• CAS: 924889-41-8
• 化学式: C₁₈H₃₀O₂
• 分子量: 278.435
• InChiKey: PIVKRPXWMMXFSF-KTKRTIGZSA-N

物化性质

• 沸点：
  398.3±42.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-tridec-4-en-6-ynyloxy-tetrahydro-pyran 在 正丁基锂 、 四丙基高钌酸铵 、 4 A molecular sieve 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 33.25h， 生成 (2SR,3RS)-2-[(3E)-3,5-hexadienyl]-3-(1-octynyl)oxirane
  参考文献：
  名称：

  Dicobaltoctacarbonyl-Mediated Synthesis of Tricyclic 5,6-Diydropyran-2-one Derivatives via Tandem Cycloaddition Reaction between cis-Epoxyalkynes, a Tethered Olefin, and Carbon Monoxide

  摘要：

  [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%).

  DOI：

  10.1021/jo0620617
• 作为产物：
  描述：

  4-(四氢-2H-吡喃-2-基氧基)丁醛 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 sodium hexamethyldisilazane 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 2-tridec-4-en-6-ynyloxy-tetrahydro-pyran
  参考文献：
  名称：

  Dicobaltoctacarbonyl-Mediated Synthesis of Tricyclic 5,6-Diydropyran-2-one Derivatives via Tandem Cycloaddition Reaction between cis-Epoxyalkynes, a Tethered Olefin, and Carbon Monoxide

  摘要：

  [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%).

  DOI：

  10.1021/jo0620617

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%).