3-(1-羟基环己基)丙-2-炔醛 | 58678-95-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(1-羟基环己基)丙-2-炔醛
• 英文名称: 3-(1-hydroxycyclohexyl)-2-propynal
• 英文别名: 3-(1-hydroxycyclohexyl)prop-2-ynal；(1-hydroxy-cyclohexyl)-propiolaldehyde；(1-Hydroxy-cyclohexyl)-propiolaldehyd；2-Propynal, 3-(1-hydroxycyclohexyl)-
• CAS: 58678-95-8
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: DJRSVXASJAFTFW-UHFFFAOYSA-N

物化性质

• 沸点：
  106-108 °C(Press: 2.50 Torr)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3-(1-羟基环己基)丙-2-炔醛 在 叠氮基三甲基硅烷 作用下， 以 水 为溶剂， 反应 18.0h， 生成 4-(1-hydroxycyclohexyl)-1H-1,2,3-triazole-5-carbaldehyde
  参考文献：
  名称：

  Catalyst-free three-component synthesis of hydroxyalkyltriazolylmethylidene barbiturates

  摘要：

  5-[(5-Hydroxyalkyl-1H-1,2,3-triazol-4-yl)methylidene]barbiturates were eco-friendly synthesized in up to 89% yields by one-pot three-component processing (no catalyst, H2O-EtOH, room temperature, 38 h) of 4-hydroxyalkynals, trimethylsilyl azide and barbituric acids.

  DOI：

  10.1016/j.mencom.2019.11.017
• 作为产物：
  描述：

  1-(3-羟基-丙-1-炔基)-环己醇 在 2-碘酰基苯甲酸 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以80%的产率得到3-(1-羟基环己基)丙-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
• 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.
• Cycloaddition of Ethylenediamine to Acetylene γ-Hydroxyaldehydes
  作者：A. S. Medvedeva、I. A. Novokshonova、A. V. Afonin、L. P. Safronova

  DOI：10.1007/s11178-006-0024-x

  日期：2005.11