tridec-4-en-6-yn-1-ol | 924889-42-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tridec-4-en-6-yn-1-ol
• 英文别名: cis-tridec-4-en-6-yn-1-ol；(Z)-tridec-4-en-6-yn-1-ol
• CAS: 924889-42-9
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: MHADWKRTHKNJPD-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tridec-4-en-6-yn-1-ol 在 乙二胺四乙酸 、 四丁基硫酸氢铵 Oxone 、 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (5R)-5-[(1R)-1-hydroxynon-2-ynyl]oxolan-2-one
  参考文献：
  名称：

  手性二环氧乙烷对共轭顺式-烯炔的对映选择性环氧化

  摘要：

  本文描述的缀合的高度化疗和不对称环氧化顺使用容易获得的葡萄糖衍生的酮-enynes 2作为催化剂，臭氧作为氧化剂以形成顺式-propargyl环氧化物在高ee值的。底物的炔基与酮催化剂的恶唑烷酮部分之间的相互作用以及烯炔上的取代基与酮催化剂的恶唑烷酮部分之间的相互作用对于立体分化是重要的。

  DOI：

  10.1021/jo070205r
• 作为产物：
  描述：

  (Z)-2-((5-iodopent-4-en-1-yl)oxy)tetrahydro-2H-pyran 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 对甲苯磺酸 、 二乙胺 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 tridec-4-en-6-yn-1-ol
  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

• Zhang, Wen; Xu, Huadong; Xu, Hui, Journal of the American Chemical Society, 2009, vol. 131, p. 3832 - 3833
  作者：Zhang, Wen、Xu, Huadong、Xu, Hui、Tang, Weiping

  DOI：——

  日期：——
• Enantioselective Epoxidation of Conjugated <i>cis</i>-Enynes by Chiral Dioxirane
  作者：Christopher P. Burke、Yian Shi

  DOI：10.1021/jo070205r

  日期：2007.5.1

  This paper describes a highly chemo- and enantioselective epoxidation of conjugated cis-enynes using readily available glucose-derived ketone 2 as catalyst and Oxone as oxidant to form cis-propargyl epoxides in high ee's. The interaction between the alkyne group of the substrate and the oxazolidinone moiety of the ketone catalyst as well as the interactions between the substituents on enynes and the

  本文描述的缀合的高度化疗和不对称环氧化顺使用容易获得的葡萄糖衍生的酮-enynes 2作为催化剂，臭氧作为氧化剂以形成顺式-propargyl环氧化物在高ee值的。底物的炔基与酮催化剂的恶唑烷酮部分之间的相互作用以及烯炔上的取代基与酮催化剂的恶唑烷酮部分之间的相互作用对于立体分化是重要的。
• 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%).