2-Benzoyl-5-phenyl-penta-2.4-diensaeurenitril | 53019-99-1

• 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: 2-Benzoyl-5-phenyl-penta-2.4-diensaeurenitril
• 英文别名: 2-Benzoyl-5-phenylpenta-2,4-dienenitrile
• CAS: 53019-99-1
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: WEDNUCYPZKBHEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Benzoyl-5-phenyl-penta-2.4-diensaeurenitril 、 1-苯基-2-丙炔-1-酮 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以89%的产率得到
  参考文献：
  名称：

  Facile synthesis of highly functionalized six-membered heterocycles via PPh3-catalyzed [4+2] annulations of activated terminal alkynes and hetero-dienes: scope, mechanism, and application

  摘要：

  A novel [4+2] annulation between activated terminal alkynes and aza-dienes or oxo-dienes has been developed with the use of triphenylphosphine catalyst (20 mol %), which provides a facile method for synthesis of the corresponding highly functionalized dihydropyridines or dihydropyrans in good to excellent yields. The reaction mechanism has also been established, consisting formal hetero-Diels-Alder reaction catalyzed by PPh3 and [1,3]-proton transfer, which exhibits a large isotopic effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.043
• 作为产物：
  描述：

  反式肉桂醛 、 苯甲酰乙腈 在 哌啶 作用下， 以 苯 为溶剂， 生成 2-Benzoyl-5-phenyl-penta-2.4-diensaeurenitril
  参考文献：
  名称：

  Son,N.K. et al., Bulletin de la Societe Chimique de France, 1974, p. 471 - 474

  摘要：

  DOI：

文献信息

• Organocatalytic Domino Michael-Heterocyclization Reaction of α,β-Unsaturated Aldehydes and α-Cyano Ketones: Synthesis of Enantioenriched 4,5,6-Trisubstituted 3,4-Dihydropyranones
  作者：James O. Guevara-Pulido、José M. Andrés、Rafael Pedrosa

  DOI：10.1002/ejoc.201402982

  日期：2014.12

  electron-poor aromatic, or electron-withdrawing substituents at the β position easily react with different ketones leading to enantioenriched hemiacetals, which were further oxidized to give 4,5,6-trisubstituted-3,4-dihydropyranones in good yields and with excellent enantioselectivities. The behavior of the ketones is dependent on the α substituent of the carbonyl group, and a fine-tuning of the pKa values is

  在 β 位具有脂肪族、缺电子芳香族或吸电子取代基的 α,β-不饱和醛很容易与不同的酮反应，导致对映体富集的半缩醛，后者被进一步氧化得到 4,5,6-三取代-3,4 -二氢吡喃酮以良好的收率和优异的对映选择性。酮的行为取决于羰基的 α 取代基，需要微调 pKa 值才能获得良好的结果。
• Enantioselective Amine-Catalyzed [4+2] Annulations of Allenoates and Oxo-dienes: An Asymmetric Synthesis of Dihydropyrans
  作者：Xiaojun Wang、Tong Fang、Xiaofeng Tong

  DOI：10.1002/anie.201100945

  日期：2011.5.27

  dihydropyrans have been prepared in high to excellent yields and enantioselectivities (see scheme). The interaction between functional groups in the zwitterionic intermediate, which is generated by addition of the amine catalyst to the allenoate substrate, is thought to play a crucial role in the stereochemical outcome. Bn=benzyl, DMAP=4‐dimethylaminopyridine.

  已经以高至优异的产率和对映选择性制备了生物学上显着的多取代的二氢吡喃（参见方案）。两性离子中间体中官能团之间的相互作用（这是通过将胺催化剂添加到烯丙酸酯底物上而产生的）被认为在立体化学结果中起着至关重要的作用。Bn =苄基，DMAP = 4-二甲基氨基吡啶。
• Divergent Synthesis of Highly Substituted Tetrahydroquinolines and Cyclopentenes via Lewis Base Catalyzed Switchable [4 + 2] and [3 + 2] Annulations of MBH-Carbonates with Activated Olefins
  作者：Kai-Kai Wang、Jun Jing、Wen-Wen Zhou、Can Wang、Jun-Wei Ye、Ran Zhou、Ting-Ting Wang、Zhan-Yong Wang、Rongxiang Chen

  DOI：10.1021/acs.joc.3c00331

  日期：2023.5.5

  A highly selective and divergent synthesis which enabled access to various complex compounds is highly attractive in organic synthesis and medicinal chemistry. Herein, we developed an effective method for divergent synthesis of highly substituted tetrahydroquinolines via Lewis base catalyzed switchable annulations of Morita–Baylis–Hillman carbonates with activated olefins. The reaction displayed switchable

  能够获得各种复杂化合物的高度选择性和发散合成在有机合成和药物化学中极具吸引力。在此，我们开发了一种有效的方法，通过路易斯碱催化 Morita-Baylis-Hillman 碳酸盐与活化烯烃的可转换环化，发散合成高取代四氢喹啉。该反应通过催化剂或底物控制显示出可切换的 [4 + 2] 或 [3 + 2] 环化，提供了多种结构，其中包含高度取代的四氢喹啉或环戊烯，三个连续的立体中心带有一个季碳中心，产率高，非对映选择性好和区域选择性。此外，
• Lewis-Base-Catalyzed Enantioselective Formal [4 + 2] Annulations of Morita–Baylis–Hillman Carbonates: Access to Tetrahydroquinolines Derivatives
  作者：Yanlin He、Wei Cai、You Huang

  DOI：10.1021/acs.orglett.3c00525

  日期：2023.5.19

  The Lewis-base-catalyzed enantioselective formal [4 + 2] annulation reaction of o-acylamino-aryl MBH carbonates and electron-deficient olefins was developed. Tetrahydroquinolines with three sequential stereogenic centers containing a quaternary stereocenter were obtained in high yields with good enantioselectivity.

  开发了邻酰氨基芳基 MBH 碳酸酯和缺电子烯烃的路易斯碱催化的对映选择性缩甲醛 [4 + 2] 环化反应。以高产率和良好的对映选择性获得了具有三个连续立体中心且包含一个季立体中心的四氢喹啉。
• Son,N.K. et al., Bulletin de la Societe Chimique de France, 1974, p. 471 - 474
  作者：Son,N.K. et al.

  DOI：——

  日期：——