2-methyl-6-(4-nitrophenyl)hexa-3,5-diyn-2-ol | 100727-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-6-(4-nitrophenyl)hexa-3,5-diyn-2-ol
• CAS: 100727-43-3
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: PFMKHCIWUFMBHY-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C
• 沸点：
  393.8±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-6-(4-nitrophenyl)hexa-3,5-diyn-2-ol 在 二氧化碳 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 90.0 ℃ 、2.0 MPa 条件下， 反应 36.0h， 以87%的产率得到2,2-dimethyl-5-(4-nitrobenzyl)furan-3(2H)-one
  参考文献：
  名称：

  Carbon dioxide-mediated synthesis of 3(2H)-furanones from diyne alcohols

  摘要：

  A novel type of carbon dioxide-mediated reaction of diyne alcohols without any metal catalysts was reported. Carbon dioxide held the key to the success of this reaction, in which 3(2H)-furanones were selectively obtained in moderate to high yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.130
• 作为产物：
  描述：

  2,7-二甲基-3,5-辛二炔-2,7-二醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 生成 2-methyl-6-(4-nitrophenyl)hexa-3,5-diyn-2-ol
  参考文献：
  名称：

  铜催化的叠氮化物-炔烃环加成反应中的1-碘代-1,3-二炔类化合物：一步法合成4-乙炔基-5-碘-1,2,3-三唑

  摘要：

  发现使用碘化三（三苯基膦）铜（I）作为催化剂，将铜与有机叠氮化物催化碘代二乙炔与有机叠氮化物的1，3-偶极环加成反应是制备5-碘-4-乙炔基三唑的有效一步合成途径。该反应耐受丁二炔和叠氮化物部分中的各种官能团。还评估了所得的5-碘-4-乙炔基三唑的合成应用：Sonogashira与炔烃的偶联导致不对称取代的三唑稠合的二炔体系，而Suzuki反应产生了相应的5-芳基-4-乙炔基三唑。

  DOI：

  10.1021/acs.joc.8b02916

文献信息

• Glaser–Hay hetero-coupling in a bimetallic regime: a Ni(<scp>ii</scp>)/Ag(<scp>i</scp>) assisted base, ligand and additive free route to selective unsymmetrical 1,3-diynes
  作者：Anuradha Mohanty、Sujit Roy

  DOI：10.1039/c7cc05605b

  日期：——

  A Ni(OAc)₂/Ag(OTf) catalysed coupling of aryl alkynes and propargylic alcohol/ether/ester gave the corresponding unsymmetrical 1,3-diynes in good to excellent yields.

  Ni(OAc)2/Ag(OTf)催化的芳基炔烃和丙炔醇/醚/酯的偶联反应，产生相应的不对称1,3-二炔，收率良好至优异。
• Synthesis and molecular properties of donor–π-spacer–acceptor ynamides with up to four conjugated alkyne units
  作者：Bernhard Witulski、Torsten Schweikert、Dieter Schollmeyer、Nicolai A. Nemkovich

  DOI：10.1039/b919275a

  日期：——

  A set of push–pull ynamides with up to four conjugated triple bonds has been synthesized and the molecular properties of these new carbon rods have been characterised showing effective intramolecular charge transfers and high values for the change of the electrical dipole moment after transition from the ground to the Franck–Condon excited state.

  我们合成了一组具有多达四个共轭三键的推拉namides，并对这些新型碳棒的分子特性进行了表征，结果表明，从基态过渡到弗朗克康顿激发态后，分子内电荷转移有效，电偶极矩的变化值也很高。
• Chodkiewicz, Annales de Chimie (Cachan, France), 1957, vol. <13> 2, p. 819,861, 862
  作者：Chodkiewicz

  DOI：——

  日期：——
• Copper Catalysis for Selective Heterocoupling of Terminal Alkynes
  作者：Lebin Su、Jianyu Dong、Long Liu、Mengli Sun、Renhua Qiu、Yongbo Zhou、Shuang-Feng Yin

  DOI：10.1021/jacs.6b07984

  日期：2016.9.28

  A Cu-catalyzed selective aerobic heterocoupling of terminal alkynes is disclosed, which enables the synthesis of a broad range of unsymmetrical 1,3-diynes in good to excellent yields. The results disprove the long-held belief that homocouplings are exclusively favored in the GlaserHay reaction.
• Solid-State Polymerization of Monophenylbutadiyne Derivatives
  作者：Jun-ichi Watanabe、Harumi Yokoyama、Shuji Okada、Shigeru Takaragi、Hiro Matsuda、Hachiro Nakanishi

  DOI：10.1080/15421400902950030

  日期：2009.6.18

  Solid-state polymerization of phenylbutadiyne derivatives with o-nitro, m-nitro or p-nitro group was investigated. All monomers in bulk crystals could be thermally polymerized to become black suggesting formation of extended p-conjugation system. However, no regular polydiacetylene structures were confirmed by the structural analysis. Nanocrystals of the m-nitro derivative were prepared, and the different polymerization behavior compared with in the bulk crystals was observed.