ethyl 3-(3,5-dimethylphenyl)propiolate

• 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-(3,5-dimethylphenyl)propiolate
• 英文别名: 3-(3,5-dimethylphenyl)-2-propynoic acid ethyl ester；(3,5-Dimethyl-phenyl)-propynoic acid ethyl ester；ethyl 3-(3,5-dimethylphenyl)prop-2-ynoate
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: XOTSRASFVMUUEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3-(3,5-dimethylphenyl)propiolate 、 4-戊烯-1-醇 在 盐酸 、 palladium dichloride 作用下， 以 水 为溶剂， 反应 12.0h， 以81%的产率得到(Z)-ethyl 2-(chloro(3,5-dimethylphenyl)methylene)hept-6-enoate
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of Alkynes with Unactivated Alkenes in Ionic Liquids: A Regio- and Stereoselective Synthesis of Functionalized 1,6-Dienes and Their Analogues

  摘要：

  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.

  DOI：

  10.1021/jo402159d
• 作为产物：
  描述：

  3,5-二甲基溴苯 在 盐酸 、 双(乙腈)氯化钯(II) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 41.0h， 生成 ethyl 3-(3,5-dimethylphenyl)propiolate
  参考文献：
  名称：

  A Parallel Approach to 7-(Hetero)arylpyrazolo[1,5-a]pyrimidin-5-ones

  摘要：

  A modular, two-pot assembly of 7-arylpyrazolo[1,5-a]pyrimidones from aryl/heteroaryl halides and aminopyrazoles in library format was developed. Sonogashira coupling of aryl bromides with triethyl orthopropiolate, followed by in situ orthoester hydrolysis, provides access to beta-aryl ynoates, which undergo regioselective cyclocondensation with aminopyrazoles. The ability to vary the C7 vector of 7-arylpyrazolo[1,5-cdpyrimidones in two steps using readily available (hetero)aryl halides significantly enhances synthetic access to this challenging vector.

  DOI：

  10.1021/acscombsci.8b00032

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。
• Straightforward Approach toward Multifunctionalized Aziridines via Catalyst-Free Three-Component Reactions of α-Diazoesters, Nitrosoarenes, and Alkynes
  作者：Xing Li、Tao Feng、Dongjun Li、Honghong Chang、Wenchao Gao、Wenlong Wei

  DOI：10.1021/acs.joc.0c00368

  日期：2020.8.7

  straightforward, catalyst-free atom- and step-economical approach for the synthesis of multisubstituted 1-arylaziridine-2-carboxylates via one-pot three-component reactions of α-diazoesters, nitrosoarenes, and alkynes has been described. This method could provide facile access to a variety of multifunctionalized aziridines in up to 91% yields under mild reaction conditions and features the catalyst-free strategy

  已经描述了通过α-重氮酸酯，亚硝基芳烃和炔烃的一锅三组分反应合成多取代的1-芳基氮丙啶-2-羧酸酯的直接，无催化剂的，经济的和分步骤的方法。该方法可在温和的反应条件下以高达91％的收率轻松获得各种多功能的氮丙啶，并采用无催化剂策略，并使用廉价且容易获得的起始原料。
• Synthesis of Benzofuran Derivates via a Gold-Catalyzed Claisen Rearrangement Cascade
  作者：Yankun Li、Chen-Ho Tung、Zhenghu Xu

  DOI：10.1021/acs.orglett.2c02388

  日期：2022.8.12

  A novel method toward a facile synthesis of diverse benzofuran derivates from easily obtained quinols and alkynyl esters has been reported. A gold-catalyzed intermolecular alkoxylation/Claisen rearrangement/condensation cascade was involved. The introduction of difluorodiphenylsilane as a water-trapping reagent in the reaction leads to a higher yield.

  已经报道了一种从容易获得的喹啉和炔基酯轻松合成各种苯并呋喃衍生物的新方法。涉及金催化的分子间烷氧基化/克莱森重排/缩合级联。在反应中引入二氟二苯基硅烷作为捕水剂会导致更高的产率。
• Synthesis of Ethyl Arylpropiolates through Palladium-Catalyzed Cross-Coupling­ Reactions of Aryl Iodides with In Situ Generated Lithium Tetrakis(ethoxycarbonylethynyl)indates
  作者：Phil Lee、Youngchul Park、Dongjin Kang、Woo Jeon、Taekyu Ryu

  DOI：10.1055/s-0033-1339110

  日期：——