1,5-diphenyl-1-penten-4-yn-3-one | 16121-39-4

• 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: 1,5-diphenyl-1-penten-4-yn-3-one
• 英文别名: 1,5-Diphenyl-1-penten-4-in-3-on；1,5-Diphenylpent-1-en-4-yn-3-one
• CAS: 16121-39-4
• 化学式: C₁₇H₁₂O
• 分子量: 232.282
• InChiKey: MDUZBUIGEQDGQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914399090

反应信息

• 作为反应物：
  描述：

  1,5-diphenyl-1-penten-4-yn-3-one 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-styryl-7-phenyl-1,2,4-triazolo<3,4-b>-1,3,4-thiazepine
  参考文献：
  名称：

  Condensed systems based on 4-amino-3-mercapto-1,2,4-triazole

  摘要：

  DOI：

  10.1007/bf00473950
• 作为产物：
  描述：

  3-(Cinnamoylamino)-1-methylimidazolium hydroxide inner salt 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 24.75h， 生成 1,5-diphenyl-1-penten-4-yn-3-one
  参考文献：
  名称：

  Organometallic addition to N-(N-acyl-N-methylamino)cycloimminium salts: a general method for ketone synthesis

  摘要：

  DOI：

  10.1021/jo00073a059

文献信息

• Methylation Alkynylation of Terminal Alkenes via 1,2-Alkynyl Migration Using Dicumyl Peroxide as the Methyl Source
  作者：Yong-yue Luo、Wei Deng、Jiannan Xiang、Yi-qun Qin、De Chen、Liang Liu、Jia-jia Zhang、Xin-ju Peng

  DOI：10.1055/a-1528-8357

  日期：2021.12

  The metal-free oxidative alkene methylation/alkynylation of 1,4-enyn-3-ols with an organic peroxide as the methyl source has been developed, which provides straightforward and practical access to the challenging quaternary-carbon-containing but-3-yn-1-ones. The method is reasoned to go through methylation of functional alkenes utilizing dicumyl peroxide as the methylating reagent and subsequent intermolecular

  已开发出以有机过氧化物为甲基源的 1,4-烯炔-3-醇的无金属氧化烯烃甲基化/炔基化，这为获得具有挑战性的含季碳but-3-yn 提供了直接且实用的途径-1个。该方法被认为是通过使用过氧化二枯基作为甲基化试剂和随后的分子间环化/1,2-炔基迁移来进行功能性烯烃的甲基化。该反应具有优异的官能团耐受性、广泛的底物范围和精湛的选择性。
• Carbonylation of organic halides in the presence of terminal acetylenes; novel acetylenic ketone synthesis
  作者：Toshiaki Kobayashi、Masato Tanaka

  DOI：10.1039/c39810000333

  日期：——

  Aryl, heterocyclic, and vinylic halides react with carbon monoxide and terminal acetylenes at 120 °C or below and 80 atm or below in the presence of triethyl-amine and a catalytic amount of a palladium (II) complex to form acetylenic ketones in 46·7–92·9% yield.

  芳基，杂环和乙烯基卤化物在三乙胺和催化量的钯（II）络合物的存在下，在120°C或更低，80 atm或更低的温度下，与一氧化碳和末端乙炔反应，在46· 7–92·9％的收率。
• An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources
  作者：Pei Chen、Qian-Qian Zhang、Jia Guo、Lu-Lu Chen、Yan-Bo Wang、Xiao Zhang

  DOI：10.1039/c8ob01861h

  日期：——

  An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.

  已经建立了一种有效的膦催化方案，用于从炔烃与肟作为氢氧化物替代物来合成1,3-二酮和腈。该方法的特征在于使用膦催化剂，与各种官能团的相容性和环境温度，这使得该方法非常实用。提出了一个合理的机制。
• Palladium-catalyzed Sonogashira coupling of amides: access to ynones via C–N bond cleavage
  作者：Ming Cui、Hongxiang Wu、Junsheng Jian、Hui Wang、Chao Liu、Stelck Daniel、Zhuo Zeng

  DOI：10.1039/c6cc06428k

  日期：——

  The first palladium-catalyzed Sonogashira coupling of amides has been developed, which proceeds via a selective cleavage of the N-acylsaccharin C–N bond. The protocol is mild, highly functional group tolerant and can be efficiently employed in the synthesis of a broad array of ynones in 48–98% yields under low catalyst loading and Cu-free conditions.

  已开发出第一种钯催化的酰胺Sonogashira偶联反应，该反应通过选择性断裂N-酰基糖胺C-N键进行。该方案温和，对官能团具有很高的耐受性，并且可以在低催化剂负载和无铜条件下高效地合成广泛的炔酮，产率为48-98%。
• Synthesis of alkynyl Z-ketimines and their application in amine-catalyzed asymmetric Mannich reactions and conjugate addition
  作者：Chihiro Homma、Masahiro Yamanaka、Taichi Kano、Keiji Maruoka

  DOI：10.1016/j.tet.2021.132225

  日期：2021.7

  We developed a facile and practical synthesis of various alkynyl Z-ketimines, which can be used as a synthetic equivalent of alkyl ketimines. The obtained alkynyl Z-ketimines could be successfully applied in enantioselective Mannich reaction and conjugate addition catalyzed by a chiral amine with an acid functionality.

  我们开发了各种炔基Z-酮亚胺的简便实用的合成方法，可用作烷基酮亚胺的合成等价物。获得的炔基Z-酮亚胺可以成功地应用于具有酸官能团的手性胺催化的对映选择性曼尼希反应和共轭加成反应。