1,6-diphenylhexa-2,4-diyne-1,6-dione | 21675-25-2

• 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: 1,6-diphenylhexa-2,4-diyne-1,6-dione
• 英文别名: 1,6-Diphenyl-hexa-2,4-diin-1,6-dion
• CAS: 21675-25-2
• 化学式: C₁₈H₁₀O₂
• 分子量: 258.276
• InChiKey: AIZLRJPKKIZHBA-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C
• 沸点：
  418.0±28.0 °C(predicted)
• 密度：
  1.212±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吗啉 、 1,6-diphenylhexa-2,4-diyne-1,6-dione 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-morpholin-4-yl-1,6-diphenyl-hex-2-en-4-yne-1,6-dione
  参考文献：
  名称：

  Titova,E.I. et al., Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 1705 - 1708

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-1-苯基-2-丙炔-1-醇 在 copper(l) chloride 四甲基乙二胺 、 邻苯二甲酸二甲酯 、 氧气 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 1,6-diphenylhexa-2,4-diyne-1,6-dione
  参考文献：
  名称：

  Synthesis of linked heterocycles via use of bis-acetylenic compounds

  摘要：

  Linked bis-pyrazoles, a pyrazolyl-isoxazole, a pyrazolyl-pyrimidine and a pyrazolyl-triazole were synthesized starting with commercially available 1,4-bis(trimethylsilyl)-1,3-butadiyne 1 or readily available bis-acetylenic diketone 22. A stepwise approach based on the use of 1 allowed the synthesis of nonsymmetrically substituted bis-pyrazoles and linked heterocycles with two different cores whereas a symmetric approach based on the use of 22 allowed a very short synthesis of symmetric bis-pyrazoles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.052

文献信息

• A facile copper(i)-catalyzed homocoupling of terminal alkynes to 1,3-diynes with diaziridinone under mild conditions
  作者：Yingguang Zhu、Yian Shi

  DOI：10.1039/c3ob41621f

  日期：——

  A novel and efficient Cu(I)-catalyzed oxidative homocoupling of terminal alkynes with diaziridinone as an oxidant is described. Various terminal alkynes can be transformed into the corresponding 1,3-diynes in good yields. The reaction process is base-free, operationally simple, and amenable to the gram scale.

  描述了一种新颖且有效的 Cu( I ) 催化末端炔烃与二氮丙啶酮作为氧化剂的氧化自偶联。各种末端炔烃可以以良好的产率转化为相应的1,3-二炔烃。该反应过程无碱、操作简单且适合克级。
• Friedel-crafts reactions of bis(trimethylsilyl)polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones
  作者：D.R.M. Walton、F. Waugh

  DOI：10.1016/s0022-328x(00)89260-8

  日期：1972.4

  chloride-aluminium chloride complexes, XC6H4 COCl·AlCl3 in methylene chloride at 0–20° to form the corresponding ketones XC6H4CO(CC)nSiMe3 in excellent (n = 1) or moderate (n = 2, 4) yield. Treatment of the products with aqueous methanolic borax results in virtually quantitative liberation of the terminal alkynyl ketones XC6H4CO(CC)nH. The method provides the first practical route to the ketotetraynes (n = 4) and

  双（三甲基甲硅烷基）乙炔Me 3 Si（CC）n SiMe 3与酰氯-氯化铝络合物XC 6 H 4 COCl·AlCl 3在二氯甲烷中于0-20°反应形成相应的酮XC 6 H 4 CO（CC）n SiMe 3具有极好（n = 1）或中等（n = 2，4）的产率。用含水甲醇硼砂处理产品实际上可定量释放末端炔基酮XC 6 H 4 CO（CC）nH.该方法提供了通向酮四炔的第一种实用途径（n＝ 4），并有用地补充了现有的用于酮-单炔和-二炔合成的氧化方法。与我草酰氯氯化-铝复合发生反应3 SiCCSiMe 3，得到新的甲硅烷基取代的杂环（I）：
• Development and Application of Pyridinium 1,4-Zwitterionic Thiolates: Synthesis of Polysubstituted Thiophenes
  作者：Bin Cheng、Xiaoguang Duan、Yuntong Li、Xinping Zhang、Hui Li、Fufang Wu、Yun Li、Taimin Wang、Hongbin Zhai

  DOI：10.1002/ejoc.202000165

  日期：2020.3.31

  Pyridinium 1,4‐zwitterionic thiolates as a class of sulfur‐containing synthons were applied to a [3+2] cascade cyclization reaction with activated alkynes, affording a library of polysubstituted thiophenes with excellent regioselectivities, especially those bearing multifarious fluorine‐containing groups.

  1,4-两性离子硫醇吡啶鎓盐作为一类含硫合成子被用于与活化炔烃的[3 + 2]级联环化反应，从而提供了具有良好区域选择性的多取代噻吩文库，尤其是那些带有多个含氟基团的噻吩。
• Synthesis of 4-Pyrones by Formal Hydration of 1,3-Diynones Promoted by 1,4-Addition of Piperidine
  作者：Erandi Liyanage Perera、Daesung Lee

  DOI：10.1021/acs.orglett.2c02914

  日期：2022.9.30

  A new approach for the synthesis of 4-pyrones with broader substrate scope and functional group tolerance is described. The reaction proceeds via an initial 1,4-addition by piperidine, followed by nitrogen-assisted 6-endo-dig cyclization and hydrolysis. 1,3-Diynones with nonenolizable electron-withdrawing ketones and nonpropargylic H provide relatively high yields. For substrates with particular R2

  描述了一种合成具有更广泛底物范围和官能团耐受性的 4-吡喃酮的新方法。该反应通过哌啶的初始 1,4-加成，然后是氮辅助 6 -endo-dig环化和水解进行。具有非烯醇化吸电子酮和非炔丙基 H 的 1,3-二炔酮提供相对较高的产率。对于具有特定 R 2取代基的底物，分离出 1,4- 或 1,6-加合物，这表明 R 2取代基的空间和电子因素应该对 6 -endo-dig环化产生强烈影响。
• Iwai et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 505,508
  作者：Iwai et al.

  DOI：——

  日期：——