St_1d | 1021457-62-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: St_1d
• 英文别名: 3-Benzylidene-5-naphthalen-1-ylpent-4-yn-2-one
• CAS: 1021457-62-4
• 化学式: C₂₂H₁₆O
• 分子量: 296.368
• InChiKey: IYKPNGPJMSSBBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  St_1d 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55%的产率得到3-(azido(phenyl)methyl)-2-methyl-5-(naphthalen-1-yl) 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 St_1d
  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。
• 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。
• <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。
• Tetrasubstituted allenes by Pd0-catalyzed three-component tandem Michael addition/cross-coupling reaction
  作者：Yuanjing Xiao、Junliang Zhang

  DOI：10.1039/b919060k

  日期：——

  A Pd(0)-catalyzed three-component tandem Michael addition/cross-coupling reaction of electron-deficient enynes with nucleophiles and aryl halides was developed, which provides general, efficient, and regioselective access to multi-functionalized tetra-substituted allenes.

  开发了Pd（0）催化的缺电子烯炔与亲核试剂和芳基卤化物的三组分串联迈克尔加成/交叉偶联反应，该反应可提供通用，有效和区域选择性的多官能化四取代烯。
• Tetrasubstituted furans by PdII/CuI-cocatalyzed three-component domino reactions of 2-(1-alkynyl)-2-alken-1-ones, nucleophiles and diaryliodonium salts
  作者：Wenbo Li、Junliang Zhang

  DOI：10.1039/c0cc03450a

  日期：——

  A novel Pd(OAc)(2)/CuI-cocatalyzed three-component reaction of 2-(1-alkynyl)-2-alken-1-ones, nucleophiles and diaryliodonium salts has been developed. The procedure allows the synthesis of tetrasubstituted furans in good to high yields under mild conditions.

  开发了一种新型的Pd（OAc）（2）/ CuI催化的2-（1-炔基）-2-链烯-1-酮，亲核试剂和二芳基碘鎓盐的三组分反应。该程序允许在温和的条件下以高至高的产率合成四取代的呋喃。