4-羟基-4-甲基己-2-炔醛 | 58678-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-羟基-4-甲基己-2-炔醛
• 英文名称: 4-hydroxy-4-methyl-2-hexynal
• 英文别名: 4-hydroxy-4-methylhex-2-ynal；4-hydroxy-4-methyl-hex-2-ynal
• CAS: 58678-93-6
• 化学式: C₇H₁₀O₂
• mdl: MFCD07188967
• 分子量: 126.155
• InChiKey: LCRSPNGZOFSDHF-UHFFFAOYSA-N

物化性质

• 沸点：
  67-68 °C(Press: 3 Torr)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-羟基-4-甲基己-2-炔醛 在 三乙烯二胺 作用下， 以 氯仿 为溶剂， 反应 0.05h， 以50%的产率得到[5-ethyl-2-(3-hydroxy-3-methylpent-1-yn-1-yl)-5-methyl-1,3-dioxolan-4-ylidene]acetaldehyde
  参考文献：
  名称：

  Unusual opening of the 1,3-dioxolane ring in γ-hydroxy α,β-acetylenic aldehyde dimers by the action of ethylenediamine

  摘要：

  DOI：

  10.1134/s1070428008080289
• 作为产物：
  描述：

  4-Methyl-1,4-hydroxy-hexin-(2) 在 2-碘酰基苯甲酸 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以81%的产率得到4-羟基-4-甲基己-2-炔醛
  参考文献：
  名称：

  An Efficient Oxidation of Element-Containing Propargyl Alcohols and Acetylenic γ-Diols by 2-Iodoxybenzoic Acid (IBX)

  摘要：

  报告了一种高效便捷的乙炔醇和二醇通过邻碘氧基苯甲酸（IBX）进行氧化的方法。仅需将相应的醇与悬浮于丙酮或四氢呋喃中的IBX简单加热，即可高产率地获得含硅（锗）丙炔醛或γ-羟基丙炔醛。

  DOI：

  10.1055/s-0028-1087225

文献信息

• Facile one-pot synthesis of 5-substituted isoxazoles and pyrazoles through microwave-promoted intramolecular cyclization of <font>γ</font>-hydroxyalkynal oximes and hydrazones
  作者：Denis A. Bulanov、Irina A. Novokshonova、Vladimir V. Novokshonov、Igor A. Ushakov、Irina V. Sterkhova

  DOI：10.1080/00397911.2016.1263892

  日期：2017.2.16

  ABSTRACT Simple and efficient one-pot synthesis of 5-substituted isoxazoles and pyrazoles has been developed. The formation of the target isoxazoles and pyrazoles is initiated by 1,2-nucleophilic addition of generated in situ hydroxylamine or hydrazine to α-acetylenic γ-hydroxyaldehydes with further intramolecular cyclization of the adducts. The protocols are associated with readily available substrates

  摘要 5-取代异恶唑和吡唑的简单高效的一锅法合成已经被开发出来。目标异恶唑和吡唑的形成是通过将生成的羟胺或肼与 α-炔属 γ-羟基醛进行 1,2- 亲核加成以及加合物的进一步分子内环化而引发的。这些协议与容易获得的底物、简单的程序、短的反应时间和中等至高的产量有关。图形概要
• The aldol-type condensation of methyl diazoacetate with 3-organyl-silyl and -germyl propynals and their carbon analogues
  作者：O.I. Margorskaya、A.S. Medvedeva、M.M. Demina、I.D. Kalikhman、M.G. Voronkov

  DOI：10.1016/0022-328x(89)88071-4

  日期：1989.10

  addition of methyl diazoacetate (I) to the carbonyl group of the substituted propyn-1-als RCCCHO (II) (R = alkyl, Alk3Si, Et3Ge) to give the corresponding methyl esters of 2-diazo-3-hydroxy-4-pentyn carboxylic acid RCCCH(OH)C(N2)COOMe (III) have been found. Shielding of the triple bond in II by the bulky R group or complexation with dicobalt octacarbonyl, the presence of strong electron acceptor

  未催化，选择性地将重氮乙酸甲酯（I）加至取代的丙炔基1-丙二醛RCCCHO（II）（R =烷基，Alk 3 Si，Et 3 Ge）的羰基上的最佳条件已经发现2-重氮-3-羟基-4-戊炔羧酸RC ＝ CCH（OH）C（N 2）COOMe（III）的相应甲酯。通过庞大的R基团屏蔽二代中的三键，或与二钴八羰基二钴络合，在二代的3位上存在强电子受体（4-NO 2 C 6 H 4），并且溶剂的极性低在选择性羟醛缩合中。γ-羟基丙醛R 1 R 2的反应具有重氮乙酸甲酯的C（OH）＝ CCHO也通过醛醇型加成而进行，并且涉及两个丙炔分子，形成二炔基重氮四环（VIII）。将重氮乙酸甲酯的β加成到三烷基甲硅烷基或-锗基丙炔中的三键上，得到异构的甲酰基吡唑IV和V.IV的4位上含Si或Ge的取代基的存在会促进它们的二聚为三环半胱氨酸，VI。
• Synthesis of 4-Alkynyl-substituted 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones
  作者：Vladimir V. Novokshonov、Irina A. Novokshonova、Hien T. T. Nguyen、Alevtina S. Medvedeva

  DOI：10.1080/00397911.2011.556298

  日期：2012.8.15

  4-Alkynyl-3,4-dihydropyrimidin-2-(1H)-ones were synthesized by a one-pot reaction of propynals, ethyl acetoacetate, and urea. The yields of acetylenic dihydropyrimidinones depend significantly upon the propynal structure and catalyst type. A comparative study of the catalysts revealed an important advantage of polyphosphate ester in tetrahydrofuran in comparison with hydrochloric acid in methanol or trimethylchlorosilane in dimethylformamide, allowing the preparation of target compounds in good or moderate yields.
• Synthesis of acetylenic ? -hydroxy aldehydes and their reaction with primary amines
  作者：A. S. Medvedeva、L. P. Safronova、G. G. Chichkareva、M. G. Voronkov

  DOI：10.1007/bf00925629

  日期：1976.1
• Decisive role of water in efficient noncatalyzed synthesis of polyfunctional 1H-1,2,3-triazoles proceeding from γ-hydroxypropynals
  作者：A. S. Medvedeva、M. M. Demina、T. L. H. Nguyen、T. D. Vu、D. A. Bulanov、V. V. Novokshonov

  DOI：10.1134/s1070428013080216

  日期：2013.8

  A highly efficient method was developed for the synthesis of new polyfunctional 1H-1,2,3-triazoles by the reaction of gamma-hydroxypropynals with trimethylsilyl azide in water at room temperature without catalyst. The addition of trimethylsilyl azide to gamma-hydroxypropynals occurs regioselectively: Previously unknown hydroxyalkyl-1H-1,2,3-triazolecarbaldehydes have been isolated in 69-96% yields with the prevalence of 1,5-isomers and the content of minor 1,4-isomers equal 9-21%. In the reaction of gamma-hydroxypropynals with sodium azide in DMSO the formation of 4-hydroxyalkyl-1H-1,2,3-triazole-5-carbaldehydes is accompanied by the dimerization of initial aldehydes into the corresponding 1,3-dioxolanes.