Ethyl 3-(4-ethenylphenyl)prop-2-ynoate | 1511356-93-6

• 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: Ethyl 3-(4-ethenylphenyl)prop-2-ynoate
• 英文别名: ethyl 3-(4-ethenylphenyl)prop-2-ynoate
• CAS: 1511356-93-6
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: PFKKYILEHHERMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  异氰酸叔丁酯 、 Ethyl 3-(4-ethenylphenyl)prop-2-ynoate 在 水 、 palladium diacetate 、 potassium bromide 、 盐酸 作用下， 以 甲苯 为溶剂， 反应 13.0h， 以80%的产率得到ethyl 1-(tert-butyl)-2,5-dioxo-4-(4-vinylphenyl)-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  通过钯催化的炔烃与异氰酸酯的环化反应组装多取代的马来酰亚胺

  摘要：

  本文描述了炔烃与异氰化物的有效且方便的钯催化的环化反应。该方案允许在水解后以宽范围的底物和温和的反应条件实际合成许多有价值的多取代的马来酰亚胺衍生物。在此转换中构建了C–C，C = O和C–N键，异氰酸酯同时作为C和N的来源。

  DOI：

  10.1021/acs.joc.6b02227

文献信息

• Novel palladium-catalyzed cascade carboxylative annulation to construct functionalized γ-lactones in ionic liquids
  作者：Jianxiao Li、Shaorong Yang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c3cc48052f

  日期：——

  A novel palladium-catalyzed, one-pot, four-step cascade method has been developed to afford functionalized gamma-lactones in moderate to good yields. This novel and general methodology represents a rare instance of carbonylation of the C(sp(3))-palladium bond.

  已经开发出新颖的钯催化的一锅四步级联方法，以中等至良好的产率提供官能化的γ-内酯。这种新颖而通用的方法代表了C（sp（3））-钯键羰基化的罕见实例。
• Palladium-Catalyzed Intermolecular Aerobic Annulation of <i>o</i>-Alkenylanilines and Alkynes for Quinoline Synthesis
  作者：Jia Zheng、Zun Li、Liangbin Huang、Wanqing Wu、Jianxiao Li、Huanfeng Jiang

  DOI：10.1021/acs.orglett.6b01008

  日期：2016.8.5

  A new approach to construct 2,3-disubstituted quinolines is described via Pd-catalyzed oxidative cyclization of o-vinylanilines and alkynes with molecular oxygen. This transformation is supposed to undergo intermolecular amination of alkyne, insertion of the olefin, and oxidative cleavage of C–C bond sequence.

  通过Pd催化邻乙烯基苯胺和炔烃与分子氧的氧化环化，描述了一种构建2,3-二取代喹啉的新方法。据认为，这种转变经历了炔烃的分子间胺化，烯烃的插入以及C–C键序列的氧化裂解。
• Palladium‐Catalyzed Cascade Annulation To Construct Functionalized β‐ and γ‐Lactones in Ionic Liquids
  作者：Jianxiao Li、Wanfei Yang、Shaorong Yang、Liangbin Huang、Wanqing Wu、Yadong Sun、Huanfeng Jiang

  DOI：10.1002/anie.201403341

  日期：2014.7.7

  A highly efficient and mild palladium‐catalyzed, one‐pot, four‐step cascade annulation has been developed to afford functionalized β‐ and γ‐lactones in moderate to good yields with high regio‐ and diastereoselectivities in ionic liquids. The employment of ionic liquids under mild reaction conditions makes this transformation green and practical. Especially, this reaction provided a novel and convenient

  已经开发出了一种高效，温和的钯催化，一锅，四步级联反应，以中等至良好的产率提供官能化的β-和γ-内酯，并在离子液体中具有较高的区域选择性和非对映选择性。在温和的反应条件下使用离子液体使这种转化绿色而实用。特别是，该反应为构建天然存在的生物活性β-和γ-内酯提供了一种新颖便捷的方法。
• B₂pin₂-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O₂ as Oxygen Source and Sole Oxidant
  作者：Jiuzhong Huang、Lu Ouyang、Jianxiao Li、Jia Zheng、Wuxin Yan、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.8b01806

  日期：2018.9.7

  A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.
• Palladium-Catalyzed Coupling of Alkynes with Unactivated Alkenes in Ionic Liquids: A Regio- and Stereoselective Synthesis of Functionalized 1,6-Dienes and Their Analogues
  作者：Jianxiao Li、Shaorong Yang、Huanfeng Jiang、Wanqing Wu、Jinwu Zhao

  DOI：10.1021/jo402159d

  日期：2013.12.20

  A palladium-catalyzed regio- and stereoselective intermolecular tandem reaction of alkynes and unactivated 1,6-ionic liquids is described, providing a practical, efficient, and versatile method for the synthesis of functionalized 1,6-dienes in moderate to good yields. The present reaction has high functional-group tolerance and gives products on a gram scale. Mechanistic studies indicate that the reaction might proceed via a chain-walking mechanism.