1-(1,1-dimethylethyl)-5-phenyl-1,4-pentadiyn-3-one | 162467-55-2

• 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-(1,1-dimethylethyl)-5-phenyl-1,4-pentadiyn-3-one
• 英文别名: 1-phenyl-6,6-dimethyl-hepta-1,4-diyne-3-one；1-Phenyl-5-tert-butyl-1,4-pentadiyn-3-one；6,6-dimethyl-1-phenylhepta-1,4-diyn-3-one；1-(1,1-Dimethylethyl)-5-phenyl-1,4-pentadiyn-3-al
• CAS: 162467-55-2
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: XKOVHAGVAAPIEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1,1-dimethylethyl)-5-phenyl-1,4-pentadiyn-3-one 在 正丁基锂 、 氢化钾 作用下， 以 氘代四氢呋喃 、 乙醚 为溶剂， 生成
  参考文献：
  名称：

  交叉共轭烯二炔还原伯格曼型环化成富烯和富瓦烯阴离子：取代基的作用

  摘要：

  各种交叉共轭的烯二炔在用金属钾还原后经历“伯格曼型”环芳构化，生成富烯和富瓦烯衍生物的阴离子。这种新的阴离子环化比使用线性烯二炔的经典 Bergman 环化容易得多，在 -78 摄氏度时产生高反应性双自由基。并非所有交叉共轭的烯二炔在还原时都会产生环化双阴离子。一些产生未环化的、Y 形的、交叉共轭的二价阴离子，而另一些显然产生二聚化或作为单体持续存在的自由基阴离子。一个系统产生环化和未环化的二价阴离子。因此，取代基被证明是决定还原结果的关键因素。环化发生在由取代基控制的特定“机会窗口”内。

  DOI：

  10.1021/ja0566477
• 作为产物：
  描述：

  6,6-dimethyl-1-phenylhepta-1,4-diyn-3-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 1-(1,1-dimethylethyl)-5-phenyl-1,4-pentadiyn-3-one
  参考文献：
  名称：

  二炔酮和邻羟基芳基甲亚胺叶立德的连续[3+2]和[4+4]环化：二氢吡咯稠合八元环支架的构建

  摘要：

  我们开发了二炔酮和邻羟基芳香醛亚胺在温和条件下的级联反应。该方案建议通过连续的[3+2]/[4+4]环加成和质子转移过程进行，从而为合成各种二氢吡咯稠合八元环支架提供有效的方法。

  DOI：

  10.1002/adsc.202300998

文献信息

• Phosphine-Catalyzed Synthesis of 3-Allyl-4-pyrones by the Tandem Reaction of Diynones and Allylic Alcohols
  作者：Ya-Fang Ye、Wan-Wan Yang、Jing-Wen Zhang、Ji-Ya Fu、Jun-Yan Zhu、Yan-Bo Wang

  DOI：10.1021/acs.joc.1c01340

  日期：2021.11.5

  A simple and effective tandem reaction of diynones and allylic alcohols was developed to afford functionalized 3-allyl-4-pyrones in moderate to excellent yields. This protocol underwent a Michael addition─Claisen rearrangement─O-cyclization process, which exhibited broad substrate tolerance, high regioselectivity, and atom economy under a metal-free condition. Moreover, functional transformation of

  开发了一种简单有效的二炔酮和烯丙醇的串联反应，以中等至优异的产率提供官能化的 3-allyl-4-pyrones。该协议经历了迈克尔加成─克莱森重排─O-环化过程，在无金属条件下表现出广泛的底物耐受性、高区域选择性和原子经济性。此外，还进一步研究了产品的功能转化。
• Method for preparation of an intermediate dye product
  申请人：——

  公开号：US20020022723A1

  公开（公告）日：2002-02-21

  The present invention provides a novel method for the synthesis of an intermediate dye product having the following formula: 1 wherein L is S, Te, or Se; R 1 and R 2 are either the same or different aryl or alkyl compounds; R 3 is hydrogen or a short chain alkyl group; and Z is an anion. The process to formulate this intermediate compound entails reacting an R 1 -acetylene compound with an R 2 -acetylene compound (compounds A) into an enol ether compound with the R 1 and/or R 2 constituents (compound D) And from compound D, it forms into an intermediate dye compound having an L-based cyclic ring with the R 1 and/or R 2 constituents (compound F). With compound F the desired dye can be made with a greater overall yield for mass production.

  本发明提供了一种合成中间染料产物的新方法，其具有以下结构式：其中L为S、Te或Se；R1和R2为相同或不同的芳香族或烷基化合物；R3为氢或短链烷基基团；Z为阴离子。制备这种中间化合物的过程包括将R1-乙炔化合物与R2-乙炔化合物（化合物A）反应成为具有R1和/或R2组分的烯醚化合物（化合物D），然后从化合物D形成具有基于L的环状环的中间染料化合物，其中含有R1和/或R2组分（化合物F）。通过化合物F，可实现所需染料的更高总产量，用于大规模生产。
• Synthesis of 4-(Iso)Quinolinyl-3(<i>2H</i> )-furanones from (Iso)Quinoline <i>N</i> -oxides and 1,4-Diyn-3-ones: A Comparison of Copper Catalysis and Metal-free Reaction
  作者：Xuetong Li、Tao Wang、Zunting Zhang

  DOI：10.1002/adsc.201801382

  日期：2019.2.19

  A facile synthesis of (iso)quinolinyl‐3(2H)‐furanones from (iso)quinoline N‐oxides and 1,4‐diyn‐3‐ones in the presence of copper catalyst or under metal‐free conditions was developed. The resulting (iso)quinolinyl‐3(2H)‐furanones could be easily converted to (iso)quinolinyl‐isoxazoles, pyrazoles and polycyclic (iso)quinoline derivatives. In addition, the success in one‐pot, metal‐free synthesis of

  在铜催化剂存在下或在无金属条件下，由（异）喹啉N-氧化物和1,4-二炔基-3-酮可轻松合成（异）喹啉基-3（2H）-呋喃酮。生成的（iso）quinolinyl-3（2H）-呋喃酮很容易转化为（iso）quinolinyl-isoxazoles，吡唑和多环（iso）quinoline衍生物。此外，从异喹啉开始一锅法无金属合成异喹啉基-3（2H）-呋喃酮的成功表明，该方法具有对吡啶，喹啉和异喹啉进行无金属衍生化的能力。
• A Comparison of Linear Optical Properties and Redox Properties in Chalcogenopyrylium Dyes Bearing Ortho-Substituted Aryl Substituents and <i>tert</i>-Butyl Substituents
  作者：Jagannath Panda、Peter R. Virkler、Michael R. Detty

  DOI：10.1021/jo026645u

  日期：2003.3.1

  A series of thiapyrylium pentamethine dyes (4 and 12-15) bearing 2,2'-di-tert-butyl-6,6'-diphenyl, 2,2'-di-tert-butyl-6,6'-bis(2,6-dimethylphenyl), 2,2'-di-tert-butyl-6,6'-bis(2-methylphenyl), 2,2',6,6'-tetrakis(2,6-dimethylphenyl), and 2,2',6,6'-tetrakis(2-methylphenyl) substituents, respectively, were prepared and their linear optical properties and electrochemical redox properties were measured and compared to thiapyrylium pentamethine dyes 3 and 5. The tert-butyl and 2,6-dimethylphenyl substituents give nearly identical chromophores with respect to values of lambda(max), molar extinction coefficients (epsilon), bandwidths at half-height (v(1/2)), and lack of absorption in the visible spectrum. The 2-methylphenyl substituent imparts linear optical properties that are intermediate between those of the tert-butyl and phenyl substituents. The 2,6-dimethylphenyl and 2-methylphenyl substituents impart greater oxidative stability based on anodic shifts in oxidation potential.
• Syntheses of 4H-Thiopyran-4-one 1,1-Dioxides as Precursors to Sulfone-Containing Analogs of Tetracyanoquinodimethane
  作者：N. Geoffrey Rule、Michael R. Detty、Jeanne E. Kaeding、John A. Sinicropi

  DOI：10.1021/jo00111a027

  日期：1995.3

  Synthetic routes to the unsubstituted 4H-thiopyran-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation af 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.