3-phenyl-2-(thiophene-2-carbonyl)prop-2-enenitrile | 161952-32-5

• 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: 3-phenyl-2-(thiophene-2-carbonyl)prop-2-enenitrile
• CAS: 161952-32-5
• 化学式: C₁₄H₉NOS
• 分子量: 239.298
• InChiKey: DJJODFKJMAWXNO-UHFFFAOYSA-N

物化性质

• 沸点：
  407.1±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  硝基乙烯 、 3-phenyl-2-(thiophene-2-carbonyl)prop-2-enenitrile 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 3-nitro-4-phenyl-6-(thiophen-2-yl)-3,4-dihydro-2H-pyran-5-carbonitrile
  参考文献：
  名称：

  使用硝基乙烯和烯酮进行膦催化的甲醛[4 + 2]环化反应：二氢吡喃的对映选择性合成

  摘要：

  已经开发出了第一个膦催化的硝基乙烯与α-氰基-α，β-不饱和酮之间的对映体选择性oxa- [4 + 2]反应。在基于二肽的膦催化剂和非手性布朗斯台德酸添加剂的存在下，获得了具有出色的对映选择性和非对映选择性的高度官能化的3,4-二氢-2 H-吡喃。

  DOI：

  10.1021/acs.orglett.8b02519

文献信息

• Enantioselective [4 + 2]-Annulation of Oxadienes and Allenones Catalyzed by an Amino Acid Derived Phosphine: Synthesis of Functionalized Dihydropyrans
  作者：Huanzhen Ni、Weijun Yao、Abdul Waheed、Nisar Ullah、Yixin Lu

  DOI：10.1021/acs.orglett.6b00760

  日期：2016.5.6

  An enantioselective [4 + 2]-annulation process between cyano-activated oxadienes and allenones is developed. An l-valine-derived phosphine was efficient in catalyzing the reaction, and a wide range of highly functionalized dihydropyrans were prepared in high yields and with excellent enantioselectivities.

  建立了氰基活化的二氧杂环丁烯与烯丙基之间的对映选择性[4 + 2]环化过程。一升-缬氨酸衍生膦是催化反应高效，并且以高产率和具有优异的对映选择性制备一个宽范围的高度功能的二氢吡喃。
• 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。
• Asymmetric Inverse-Electron-Demand Oxa-Diels–Alder Reaction with Morita–Baylis–Hillman Carbonates of 2-Cyclopentenone via a Palladium-Catalyzed Umpolung Strategy
  作者：Jia-Le Zheng、Fei Liu、Xue Song、Zhi Zhao、Wei Du、Ying-Chun Chen

  DOI：10.1021/acs.joc.2c02350

  日期：——

  Morita–Baylis–Hillman carbonates of 2-cyclopentenone under Pd(0) catalysis could be umpolunged by regioselectively forming η2-Pd(0) complexes via π-Lewis base activation, and underwent asymmetric inverse-electron-demand oxa-Diels–Alder reaction with α-cyano chalcones. An array of fused pyran frameworks with dense substitutions was constructed with excellent stereoselectivity (up to 99% ee, >19:1 dr), which could

  在这里，我们发现2-环戊烯酮的Morita-Baylis-Hillman碳酸盐在Pd(0)催化下生成的二烯酮可以通过π-Lewis碱活化区域选择性地形成η 2 -Pd(0)络合物而发生反极化，并经历不对称逆反应- 与 α-氰基查尔酮的电子需求 oxa-Diels-Alder 反应。构建了一系列具有密集取代的稠合吡喃框架，具有出色的立体选择性（高达 99% ee，>19:1 dr），可以对其进行精心设计以获得具有更高分子复杂性的对映体富集结构。
• 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
  作者：Qiongmei Zhang、Tong Fang、Xiaofeng Tong

  DOI：10.1016/j.tet.2010.07.043

  日期：2010.10

  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.