1,5-bis(4-chlorophenyl)penta-1,4-diyn-3-one | 34793-65-2

• 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: 1,5-bis(4-chlorophenyl)penta-1,4-diyn-3-one
• 英文别名: 3-Oxo-1,5-(4,4'-dichlor)diphenylpentadiin；1,4-Pentadiyn-3-one, 1,5-bis(4-chlorophenyl)-
• CAS: 34793-65-2
• 化学式: C₁₇H₈Cl₂O
• 分子量: 299.156
• InChiKey: JZZMCHUJYRMPQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  2
• 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

反应信息

• 作为反应物：
  描述：

  1,5-bis(4-chlorophenyl)penta-1,4-diyn-3-one 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以61%的产率得到2,6-二(4-氯苯基)吡喃-4-酮
  参考文献：
  名称：

  布朗斯台德酸催化和NIS促进的二炔酮环化：4-吡喃酮，4-吡啶酮和3-吡咯烷酮衍生物的选择性合成

  摘要：

  发现布朗斯台德酸催化的串联环化对于从二炔酮制备一系列多取代的4-吡喃酮非常有效（收率高达99％）。还通过使用NIS和/或布朗斯台德酸选择性地合成了4-吡啶酮和3-吡咯烷酮衍生物。NIS作为亲电子试剂可以在非常温和的反应条件下有效而迅速地促进这些反应。

  DOI：

  10.1021/jo402055a
• 作为产物：
  描述：

  1-氯-4-(2,2-二溴乙烯基)苯 在 manganese(IV) oxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 1,5-bis(4-chlorophenyl)penta-1,4-diyn-3-one
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y

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。
• 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。
• Sequential [3+2] and [4+4] Annulation of Diynone and <i>o</i>‐Hydroxyaryl Azomethine Ylide: Construction of Dihydropyrrole Fused Eight‐Membered Ring Scaffold
  作者：Jie Shen、Yu Xing、Lidong Fu、Yanze Li、Lei Cui、Zijun Zhou、Chunju Li、Jian Li

  DOI：10.1002/adsc.202300998

  日期：2023.12.5

  We developed a cascade reaction of diynone and o-hydroxy aromatic aldimine under mild conditions. This protocol is proposed to proceed through sequential [3+2]/[4+4] cycloaddition and proton transfer processes, thus providing an efficient way for the synthesis of a variety of dihydropyrrole fused eight-membered ring scaffolds.

  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。
• Mueller,E.; Segnitz,A., Justus Liebigs Annalen der Chemie, 1973, p. 1583 - 1591
  作者：Mueller,E.、Segnitz,A.

  DOI：——

  日期：——
• Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4-Pyrone, 4-Pyridone, and 3-Pyrrolone Derivatives
  作者：Yi-Feng Qiu、Fang Yang、Zi-Hang Qiu、Mei-Jin Zhong、Li-Jing Wang、Yu-Ying Ye、Bo Song、Yong-Min Liang

  DOI：10.1021/jo402055a

  日期：2013.12.6

  Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

  发现布朗斯台德酸催化的串联环化对于从二炔酮制备一系列多取代的4-吡喃酮非常有效（收率高达99％）。还通过使用NIS和/或布朗斯台德酸选择性地合成了4-吡啶酮和3-吡咯烷酮衍生物。NIS作为亲电子试剂可以在非常温和的反应条件下有效而迅速地促进这些反应。