2-benzylidene-1-(4-chlorophenyl)-4-phenyl-3-butyn-1-one | 1221289-09-3

• 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-benzylidene-1-(4-chlorophenyl)-4-phenyl-3-butyn-1-one
• 英文别名: 2-Benzylidene-1-(4-chlorophenyl)-4-phenylbut-3-yn-1-one
• CAS: 1221289-09-3
• 化学式: C₂₃H₁₅ClO
• 分子量: 342.825
• InChiKey: HPWYTFDLFNCUTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• 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：

  2-benzylidene-1-(4-chlorophenyl)-4-phenyl-3-butyn-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67%的产率得到3-(azido(phenyl)methyl)-2-(4-chlorophenyl)-5-phenylfuran
  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'-chlorochalcone 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溴 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-benzylidene-1-(4-chlorophenyl)-4-phenyl-3-butyn-1-one
  参考文献：
  名称：

  铜催化炔基取代烯酮的对映选择性1,4-原硅烷基化合成高度非对映异构手性高烯基硅烷

  摘要：

  开发了一种铜催化的 α-炔基-烯酮的 1,4-原甲硅烷基化，以形成官能化的手性高烯基硅烷。在手性单吡啶恶唑啉配体的存在下，以良好的收率制备了多种具有连续立体中心和轴的三取代丙二烯衍生物，具有优异的对映选择性和非对映选择性。

  DOI：

  10.1021/acs.orglett.2c00739

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。
• Asymmetric Construction of 2,3-Dihydroisoxazoles via an Organocatalytic Formal [3 + 2] Cycloaddition of Enynes with <i>N</i>-Hydroxylamines
  作者：Wenbo Li、Xiuzhao Yu、Zhenting Yue、Junliang Zhang

  DOI：10.1021/acs.orglett.6b01737

  日期：2016.8.19

  An organocatalytic asymmetric formal [3 + 2] cycloaddition of enynones with N-hydroxylamines has been described. A newly designed multifunctional organocatalyst was found to be highly effective, and the method allowed the synthesis of a variety of 2,3-dihydroisoxazoles in good yields with excellent enantioselectivity.

  已经描述了烯酮与N-羟胺的有机催化不对称的正式[3 + 2]环加成反应。发现一种新设计的多功能有机催化剂非常有效，该方法可以良好的收率和优异的对映选择性合成多种2,3-二氢异恶唑。
• Dinucleophilic Reactivity of Isocyanoacetate: Base-Catalyzed One-Pot Access to 4-Azafluorenes and 4-Azafluorenones
  作者：Xin Wang、Jinhuan Dong、Xianxiu Xu、Bo Tang

  DOI：10.1021/acs.orglett.1c03314

  日期：2021.12.3

  A base-catalyzed double annulation of isocyanoacetates with various enynones has been developed for the expeditious synthesis of 4-azafluorene and 4-azafluorenone derivatives. Against the well-known 1,3-dipolar reactivities, the active methylene and isocyano groups of isocyanoacetate serve as nucleophiles in this domino transformation.

  为了快速合成 4-氮杂芴和 4-氮杂芴酮衍生物，开发了一种碱催化异氰基乙酸酯与各种烯炔酮的双环化。针对众所周知的 1,3-偶极反应性，异氰基乙酸酯的活性亚甲基和异氰基基团在这种多米诺骨牌转换中充当亲核试剂。
• Gold-catalyzed sequential annulations towards 3,4-fused bi/tri-cyclic furans involving a [3+2+2]-cycloaddition
  作者：Suna Liu、Pu Yang、Shiyong Peng、Chenghao Zhu、Shengyu Cao、Jian Li、Jiangtao Sun

  DOI：10.1039/c6cc09154g

  日期：——

  A gold-catalyzed sequential annulation towards 3,4-fused bicyclic furan compounds has been realized by employing 2-(1-alkynyl)-2-alken-1-ones and 1,3,5-triazines as the starting materials under mild reaction conditions. This protocol features the multiple...

  通过以2-（1-炔基）-2-烯烃-1-酮和1,3,5-三嗪为起始原料在温和反应下实现了金催化的3,4-稠合双环呋喃化合物的连续环化反应条件。该协议具有多个...
• 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。