hexa-2,4-diynal | 3777-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexa-2,4-diynal
• 英文别名: Hexa-2,4-diinal；2,4-Hexadiynal
• CAS: 3777-60-4
• 化学式: C₆H₄O
• 分子量: 92.0972
• InChiKey: XLZNMAFBLLQIAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  hexa-2,4-diynal 在 四氢呋喃 、 氯化亚砜 、 乙醚 、 乙基溴化镁 作用下， 生成 tridec-1-ene-3,5,7,9,11-pentayne
  参考文献：
  名称：

  Jones et al., Journal of the Chemical Society, 1958, p. 1054,1057

  摘要：

  DOI：
• 作为产物：
  描述：

  己-2,4-二炔-1-醇 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 hexa-2,4-diynal
  参考文献：
  名称：

  Synthesis of Simple Diynals, Diynones, Their Hydrazones, and Diazo Compounds: Precursors to a Family of Dialkynyl Carbenes (R¹—C≡C—C̈—C≡C—R²)

  摘要：

  A variety of substituted pentadiynols, -diynals, and -diynones have been prepared en route to precursors to dialkynyl carbenes (R-1-C C-C-C C-R-2). In light of the marginal stability associated with these simple systems, several strategies were required to assemble the carbon backbones. The requisite five-carbon skeletons were prepared using 4 + 1, 3 2, 2 + 2 + 1, and 2 + 1 + 1 + 1 coupling methodologies. The Dess Martin periodinane serves as an excellent method for the oxidation of pentadiynols to diynals and diynones, although many of the oxidized products are sufficiently reactive that they were not isolated; rather, they were generated in situ and intercepted with nucleophiles such as tosylhydrazide or trisylhydrazide. The hydrazone derivatives are generally reliable precursors to diazo compounds and carbenes, although cyclization of the hydrazone to afford a pyrazole can be a complicating factor in certain instances.

  DOI：

  10.1021/jo101125y

文献信息

• Natural acetylenes. Part XXVIII. C17-polyacetylenic alcohols from the Umbellifer Daucus carota L. (carrot) : alkylation of benzene by acetylenyl(vinyl)carbinols in the presence of toluene-p-sulphonic acid
  作者：R. K. Bentley、D. Bhattacharjee、Ewart R. H. Jones、V. Thaller

  DOI：10.1039/j39690000685

  日期：——

  Three acetylenic compounds, the known alcohol (A; X = OH, Y = H) and diol (A; X = Y = OH) and the new monoacetate (A; X = OAc, Y = OH) have been isolated from the roots of the common carrot, Daucus carota L. H2CCH·CHX·[CC]2·CHY·CH [graphic omitted] CH·[CH2]6Me (A) When refluxed with toluene-p-sulphonic acid in benzene, the alcohol and synthetic oct-1-ene-4,6-diyn-3-ol rearranged to the expected primary

  从根中分离出三种炔属化合物，即已知的醇（A; X = OH，Y = H）和二醇（A; X = Y = OH）和新的单乙酸酯（A; X = OAc，Y = OH）公共胡萝卜，胡萝卜L.ħ 2 ç CH·CHX·[C C] 2 ·CHY·CH [图形省略] CH·[CH 2 ] 6我（A）当被回流甲苯p -sulphonic酸在苯，醇和合成的辛烯-1-烯-4,6-二炔-3-醇重排为预期的伯醇（和甲苯磺酸酯），但此外生成了PhCH 2 ·CH CH·[C C]型苯甲烃2 R，起因于溶剂的侵蚀。
• Dimerisation of polyacetylenic aldehydes with elimination of carbon monoxide
  作者：R. K. Bentley、U. Graf、Ewart R. H. Jones、R. A. M. Ross、V. Thaller、R. A. Vere Hodge

  DOI：10.1039/j39690000683

  日期：——

  Hexa-2,4-diynal, octa-2,4-diynal, and octa-2,4,6-triynal (R[CC]n·CHO) dimerise in concentrated solution with evolution of carbon monoxide, to give products of the type R[CC]n– 1·CHC(CHO)·[CC]nR; above 100° even phenylpropargyl aldehyde reacts analogously. Both geometrical isomers of the ‘dimers’ were detected and characterised.

  在浓溶液中随着六氧化二碳的逸出，六（2,4-二炔），八（2,4-二炔）和八（2,4,6-三炔）（R [CC ] n ·CHO）二聚，得到类型R [C C] n – 1 ·CH C（CHO）·[C C] n R；高于100°时，甚至苯基炔丙基醛也会发生类似反应。“二聚体”的两个几何异构体均被检测并表征。
• Easy Access to Acetal-Spiroacetal-Enol Ethers by Tandem Dearomatization of a Furan Ring and Acetalization
  作者：Biao-Lin Yin、Jin-Qiang Lai、Li Huang、Xiao-Yu Zhang、Fang-Hua Ji

  DOI：10.1055/s-0032-1316548

  日期：2012.8

  A range of structurally novel acetal-spiroacetal-enol ethers were readily synthesized from 3-[5-(methoxymethyl)-2-furyl] propionaldehydes by dearomatization to form carbocations that were trapped intramolecularly by the formyl group with subsequent acetalization.
• Synthesis of Simple Diynals, Diynones, Their Hydrazones, and Diazo Compounds: Precursors to a Family of Dialkynyl Carbenes (R¹—C≡C—C̈—C≡C—R²)
  作者：Nathan P. Bowling、Nicola J. Burrmann、Robert J. Halter、Jonathan A. Hodges、Robert J. McMahon

  DOI：10.1021/jo101125y

  日期：2010.10.1

  A variety of substituted pentadiynols, -diynals, and -diynones have been prepared en route to precursors to dialkynyl carbenes (R-1-C C-C-C C-R-2). In light of the marginal stability associated with these simple systems, several strategies were required to assemble the carbon backbones. The requisite five-carbon skeletons were prepared using 4 + 1, 3 2, 2 + 2 + 1, and 2 + 1 + 1 + 1 coupling methodologies. The Dess Martin periodinane serves as an excellent method for the oxidation of pentadiynols to diynals and diynones, although many of the oxidized products are sufficiently reactive that they were not isolated; rather, they were generated in situ and intercepted with nucleophiles such as tosylhydrazide or trisylhydrazide. The hydrazone derivatives are generally reliable precursors to diazo compounds and carbenes, although cyclization of the hydrazone to afford a pyrazole can be a complicating factor in certain instances.
• Jones et al., Journal of the Chemical Society, 1958, p. 1054,1057
  作者：Jones et al.

  DOI：——

  日期：——