3-benzylidene-5-(4-nitrophenyl)-4-pentyn-2-one | 1215082-36-2

• 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: 3-benzylidene-5-(4-nitrophenyl)-4-pentyn-2-one
• 英文别名: 3-Benzylidene-5-(4-nitrophenyl)pent-4-yn-2-one；3-benzylidene-5-(4-nitrophenyl)pent-4-yn-2-one
• CAS: 1215082-36-2
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: UVGJZRDUWCVINW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzylidene-5-(4-nitrophenyl)-4-pentyn-2-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98%的产率得到3-(azido(phenyl)methyl)-2-methyl-5-(4-nitrophenyl)furan
  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：

  苄叉丙酮 在 copper(l) iodide 、 四(三苯基膦)钯 、 溴 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 3-benzylidene-5-(4-nitrophenyl)-4-pentyn-2-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

• Highly Substituted 2,3-Dihydroisoxazoles by Et₃N-Catalyzed Tandem Reaction of Electron-Deficient 1,3-Conjugated Enynes with Hydroxylamines
  作者：Xiuzhao Yu、Bo Du、Kai Wang、Junliang Zhang

  DOI：10.1021/ol100490y

  日期：2010.4.16

  reaction of electron-deficient 1,3-conjugated enynes with hydroxylamines was developed which provided rapid, metal-free, and regioselective access to highly substituted multifunctionalized 2,3-dihydroisoxazoles under mild conditions. The reactions of 3-(2-arylethynyl)-4H-chromen-4-ones with hydroxylamines afford β-amino enones under the same reaction conditions.

  开发了一种Et 3 N催化的缺电子的1,3-共轭烯炔与羟胺的串联反应，该反应可在温和条件下快速，无金属和区域选择性地接近高度取代的多官能化2,3-二氢异恶唑。在相同的反应条件下，3-（2-芳基乙炔基）-4 H-铬烯-4-酮与羟胺的反应得到β-​​氨基烯酮。
• Enantioselective Gold(I)-Catalyzed Heterocyclization–Intermolecular Exo [4 + 3]-Cycloaddition Reactions for the Synthesis of Chiral Oxa-Bridged Benzocycloheptanes
  作者：Xiaoyu Di、Yidong Wang、Lizuo Wu、Zhan-Ming Zhang、Qiang Dai、Wenbo Li、Junliang Zhang

  DOI：10.1021/acs.orglett.9b00537

  日期：2019.5.3

  The highly exo- and enantioselective gold-catalyzed tandem heterocyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran was implemented by utilizing Ming-Phos, which provides a facile access to chiral seven-membered oxa-bridged rings in 80–98% yield with high exo selectivity (exo/endo up to 50:1) and up to 97% ee.

  高度外切-和对映选择性金催化串联heterocyclization / [4 + 3] 2-（1-炔基）环加成-2-链烯-1-酮和1,3- diphenylisobenzofuran通过利用明-PHOS实现，其提供了容易获得手性七元氧杂桥环，产率为80-98％，具有高的外切选择性（外切/内切高达50：1）和ee高达97％。
• Cationic Rhodium(I)-Catalyzed Regioselective Tandem Heterocyclization/[3+2] Cycloaddition of 2-(1-Alkynyl)-2-alken-1-ones with Alkynes
  作者：Hongyin Gao、Junliang Zhang

  DOI：10.1002/chem.201103924

  日期：2012.3.5

  RhI in two minds: A RhI‐catalyzed tandem heterocyclization/[3+2] cycloaddition reaction was developed that provides rapid, efficient, and stereoselective access to highly substituted cyclopenta[c]furans from readily available 2‐(1‐alkynyl)‐2‐alken‐1‐ones and alkynes (see scheme). The cationic RhI acts as both a Lewis acid and a conventional transition‐metal catalyst, providing the first example of

  铑我 在两个头脑：甲铑我催化的串联heterocyclization / [3 + 2]环加成反应的开发，提供了高度取代的环戊二烯并快速，高效，立体选择性接入[ C ^ ]从容易获得的2-呋喃（1-炔基） -2-烯烃-1炔烃（参见方案）。阳离子Rh I既可充当路易斯酸，又可充当常规的过渡金属催化剂，提供了充当Rhwis酸的Rh I物种的第一个实例。
• 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。
• <scp>Ming‐Phos</scp>/Gold(I)‐Catalyzed Stereodivergent Synthesis of Highly Substituted Furo[3,4‐<i>d</i>][1,2]oxazines^†
  作者：Lujia Zhou、Bing Xu、Danting Ji、Zhan‐Ming Zhang、Junliang Zhang

  DOI：10.1002/cjoc.202000034

  日期：2020.6

  A gold(I)‐catalyzed asymmetric intermolecular tandem [3+3]‐cyclization reaction of 2‐(1‐alkynyl)‐2‐ alken‐1‐ones with nitrones has been developed by using Ming‐Phos as a chiral ligand. This method enables access to the stereodivergent synthesis of highly substituted furo[3,4‐d][1,2]oxazines in excellent efficiency and stereoselectivity (up to 99% yield, 99% ee, >20 : 1 dr).

  通过使用Ming-Phos作为手性配体开发了金（I）催化的2-（1-炔基）-2-链烯-1-酮与硝酮的不对称分子间串联[3 + 3]环化反应。该方法能够以优异的效率和立体选择性（高达99％的收率，99％ee，> 20：1 dr）获得高度取代的呋喃[3,4- d ] [1,2]恶嗪的立体发散性合成。