2-(4-chlorobenzylidene)-1,4-diphenylbut-3-yn-1-one

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2-(4-chlorobenzylidene)-1,4-diphenylbut-3-yn-1-one
• 英文别名: 2-[(4-chlorophenyl)methylidene]-1,4-diphenylbut-3-yn-1-one
• 化学式: C₂₃H₁₅ClO
• 分子量: 342.825
• InChiKey: NQEQPXVTPLKLFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(4-chlorobenzylidene)-1,4-diphenylbut-3-yn-1-one 在 silver hexafluoroantimonate 、 叠氮基三甲基硅烷 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以73%的产率得到3-(azido(4-chlorophenyl)methyl)-2,5-diphenylfuran
  参考文献：
  名称：

  Rapid assembly of 3-azidomethylfurans from 2-(1-alkynyl)-2-alken-1-ones enabled by silver catalysis

  摘要：

  A rapid access to useful 3-azidomethylfurans is developed via Ag(I)-catalyzed cascade annulation/azidation of 2-(1-alkynyl)-2-alken-1-ones. The salient features of the protocol include mild reaction conditions, high efficiency, broad substrate scope, and easy scale-up. The formed azide group on the products could easily undergo further elaborations such as click cycloaddition and reduction. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131327
• 作为产物：
  描述：

  4-氯查耳酮 、 苯乙炔 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-(4-chlorobenzylidene)-1,4-diphenylbut-3-yn-1-one
  参考文献：
  名称：

  Rapid assembly of 3-azidomethylfurans from 2-(1-alkynyl)-2-alken-1-ones enabled by silver catalysis

  摘要：

  A rapid access to useful 3-azidomethylfurans is developed via Ag(I)-catalyzed cascade annulation/azidation of 2-(1-alkynyl)-2-alken-1-ones. The salient features of the protocol include mild reaction conditions, high efficiency, broad substrate scope, and easy scale-up. The formed azide group on the products could easily undergo further elaborations such as click cycloaddition and reduction. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131327

文献信息

• Catalytic Asymmetric Epoxidation of Electron-Deficient Enynes Promoted by Chiral <i>N,N′</i> -Dioxide-Scandium(III) Complex
  作者：Hang Zhang、Qian Yao、Lili Lin、Chaoran Xu、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/adsc.201700555

  日期：2017.10.4

  An asymmetric epoxidation of electron‐deficient enynes with environmentally benign aqueous hydrogen peroxide as oxidant has been accomplished by developing a chiral N,N′‐dioxide‐Scandium(III) complex catalytic system. In the presence of 0.5–2 mol% catalyst, a variety of trisubstituted alkynyl oxiranes were obtained in high yields (up to 97%) with excellent ee values (up to 99%). Furthermore, control

  通过开发手性N，N'-二氧化物-Scan（III）络合物催化体系，可以实现环境友好的过氧化氢水溶液对缺电子的炔烃的不对称环氧化。在存在0.5–2 mol％的催化剂的情况下，可以以高收率（高达97％）和优异的ee值（高达99％）获得各种三取代的炔基环氧乙烷。此外，对照实验提供了对反应机理的基本了解。
• Exo/endo selectivity-control in Lewis-acid catalyzed tandem heterocyclization/formal [4+3] cycloaddition: synthesis of polyheterocycles from 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran
  作者：Hongyin Gao、Xingxing Wu、Junliang Zhang

  DOI：10.1039/c0cc02778b

  日期：——

  tandem heterocyclization/formal [4+3] cycloaddition was developed, which provides rapid, efficient and stereoselective access to highly fused polyheterocycles from readily available 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran under mild conditions.

  开发了一种新型的催化外/内选择性选择性串联杂环/形式[4 + 3]环加成反应，该反应可从易于获得的2-（1-炔基）-2-烯烃-1快速，高效和立体选择性地进入高度稠合的多杂环。 -酮和1,3-二苯基异苯并呋喃在温和的条件下。
• Gold-Catalyzed Tandem Dual Heterocyclization of Enynones with 1,3,5-Triazines: Bicyclic Furan Synthesis and Mechanistic Insights
  作者：Yang Zheng、Yongjian Chi、Ming Bao、Lihua Qiu、Xinfang Xu

  DOI：10.1021/acs.joc.6b02947

  日期：2017.2.17

  A general and unprecedented gold-catalyzed tandem dual heterocyclization reaction of enynones with 1,3,5-triazines has been developed, which provides bicyclic fused furans in high to excellent yields under mild reaction conditions. In addition, mechanistic studies indicate that the reaction goes through a stepwise [3+2+2]-cycloaddition of furanyl gold intermediate, which is generated from gold-catalyzed

  已经开发了烯酮与1,3,5-三嗪的通用且史无前例的金催化串联双杂环反应，该反应在温和的反应条件下可提供高产率至优异产率的双环稠合呋喃。此外，机理研究表明，该反应通过呋喃基金中间体的分步[3 + 2 + 2]-环加成反应生成，该中间体是由金催化的烯酮的环化反应生成的，分子中有两个分别由1,3衍生的福尔二胺分子。 ，5-三嗪，而不是正式的[4 + 3]-环加成。
• An Unexpected Phosphine-Catalyzed Regio- and Diastereoselective [4+1] Annulation Reaction of Modified Allylic Compounds with Activated Enones
  作者：Zuliang Chen、Junliang Zhang

  DOI：10.1002/asia.201000193

  日期：——

  Rapid access: An unexpected regio‐ and diastereoselective phosphine‐catalyzed [4+1] annulation reaction of modified allylic compounds with activated enones was revealed, providing a simple, efficient route to synthesis of highly substituted 2,3‐dihydrofurans with convertible functional groups.

  快速访问：修饰的烯丙基化合物与活化的烯酮的意外的区域和非对映选择性膦催化的[4 + 1]环化反应被揭示，为合成具有可转换官能团的高度取代的2,3-二氢呋喃提供了一种简单有效的途径。
• Indium‐Catalysed Transfer Hydrogenation for the Reductive Cyclisation of 2‐Alkynyl Enones towards Trisubstituted Furans
  作者：Luomo Li、Sascha Kail、Sebastian M. Weber、Gerhard Hilt

  DOI：10.1002/anie.202109266

  日期：2021.10.25

  Indium tribromide catalysed the transfer hydrogenation from dihydroaromatic compounds, such as the commercially available γ-terpinene, to enones, which resulted in the cyclisation to trisubstituted furan derivatives. The reaction was initiated by a Michael addition of a hydride nucleophile to the enone subunit followed by a Lewis-acid-assisted cyclisation and the formation of a furan–indium intermediate

  三溴化铟催化从二氢芳香族化合物（例如市售的γ-萜品烯）到烯酮的转移氢化，从而环化为三取代的呋喃衍生物。该反应是通过将氢化物亲核试剂迈克尔加成到烯酮亚基上引发的，然后进行路易斯酸辅助环化并形成呋喃-铟中间体和衍生自二氢芳族起始材料的Wheland中间体。该产物是通过 Wheland 配合物质子化形成的，并取代了三溴化铟取代基。此外，二氢芳香族 HD 替代物的位点特异性氘标记导致了产物的位点特异性标记，并通过 H-D 加扰提供了对反应机制的有用见解。