2-((4-methoxyphenyl)ethynyl)furan | 1224168-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((4-methoxyphenyl)ethynyl)furan
• 英文别名: 2-[2-(4-Methoxyphenyl)ethynyl]furan；2-[2-(4-methoxyphenyl)ethynyl]furan
• CAS: 1224168-97-1
• 化学式: C₁₃H₁₀O₂
• 分子量: 198.221
• InChiKey: KLZLXVLHGHOYGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  315.4±22.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((4-methoxyphenyl)ethynyl)furan 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 2-(chloromethyl)-5-((4-methoxyphenyl)ethynyl)furan
  参考文献：
  名称：

  五元杂芳烃与烯丙基三丁基锡烷的钯催化区域选择性烯丙基化。

  摘要：

  在这项研究中描述了钯催化的2-（氯甲基）噻吩，2-（氯甲基）呋喃和N-保护的2-（氯甲基）-1H-吡咯与烯丙基三丁基锡烷的烯丙基化反应。这种类型的烯丙基化反应区域选择性地发生在杂芳烃环上，以令人满意的产率产生烯丙基化的脱芳香化产物或烯丙基化的杂芳烃。

  DOI：

  10.1039/c4cc10373d
• 作为产物：
  描述：

  糠醛 在 四丁基溴化铵 、 caesium carbonate 、 三苯基膦 、 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 生成 2-((4-methoxyphenyl)ethynyl)furan
  参考文献：
  名称：

  1,1-二氯烯烃在钯催化下的交叉偶联反应性：二芳基炔的多米诺合成†

  摘要：

  在钯催化的条件下，由1,1-二氯烯烃与三芳基铋试剂进行多米诺交叉偶联反应可实现二芳基炔烃的有效合成。在已建立的钯协议下，1,1-二氯烯烃显示出迄今未知的与有机金属三芳基铋试剂的显着交叉偶联反应性，以提供官能化的二芳基炔烃。

  DOI：

  10.1039/c7nj05107g

文献信息

• A straightforward alkynylation of Li and Mg metalated heterocycles with sulfonylacetylenes
  作者：Leyre Marzo、Ignacio Pérez、Francisco Yuste、José Alemán、José Luis García Ruano

  DOI：10.1039/c4cc07574a

  日期：——

  Coupling of alkynyl moieties to heterocyclic rings, without using transition metals, can be easily performed by the reaction of aryl or heteroaryl sulfonylacetylenes with heteroaryl-Li compounds or their corresponding less reactive magnesium derivatives.

  将炔基团与杂环环上偶联，而无需使用过渡金属，可以通过芳基或杂环磺酰乙炔与杂环锂化合物或其对应的反应性较低的镁衍生物反应来轻松实现。
• Base-Free Palladium-Catalyzed Sonogashira Coupling Using Organogold Complexes
  作者：Sreekumar Pankajakshan、Teck-Peng Loh

  DOI：10.1002/asia.201100263

  日期：2011.9.5

  Turn to gold: An effective protocol for base‐free Sonogashira coupling reactions using organogold complexes as nucleophilic partners has been developed. The palladium‐catalyzed methodology offers a general synthesis of aryl–alkynes under operationally simple conditions in good to excellent yields.

  转向黄金：使用有机金络合物作为亲核伴侣，开发了一种有效的无碱Sonogashira偶联反应方案。钯催化的方法可以在操作简单的条件下以高至优异的产率合成芳基炔烃。
• Cu-catalyzed decarboxylative coupling of propiolic acids with boronic acids
  作者：Leilei Shi、Wei Jia、Xun Li、Ning Jiao

  DOI：10.1016/j.tetlet.2013.01.118

  日期：2013.4

  A mild procedure of Cu-catalyzed decarboxylative cross-coupling of aryl- and alkynyl-boronic acids for construction of unsymmetrical substituted alkynes has been developed. The usage of inexpensive copper chloride as catalyst, and employing stable alkynl carboxylic acids and boronic acids as the substrates under oxidative conditions for sp-sp(2) coupling, make this method very easy to operate. (C) 2013 Elsevier Ltd. All rights reserved.
• Pd-Catalyzed Domino Synthesis of Internal Alkynes Using Triarylbismuths as Multicoupling Organometallic Nucleophiles
  作者：Maddali L. N. Rao、Deepak N. Jadhav、Priyabrata Dasgupta

  DOI：10.1021/ol1004164

  日期：2010.5.7

  The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles with 3 equiv of 1,1-dibromo-1alkenes are very fast, affording high yields of alkynes in a short reaction time. Thus, an efficient domino process has been accomplished using 1,1-dibromo-1-alkenes as surrogates for internal alkyne synthesis in couplings with triarylbismuths in a one-pot operation.
• Organocatalytic Synthesis of Alkynes
  作者：Mengnan Zhang、Tiezheng Jia、Carol Y. Wang、Patrick J. Walsh

  DOI：10.1021/jacs.5b06137

  日期：2015.8.19

  Carbon-carbon triple bonds of alkynes are ubiquitous. They serve as valuable starting materials that can be transformed into a vast array of diverse materials, with applications ranging from medicinal chemistry to electronic materials. The methods used to prepare alkynes involve stoichiometric reactions and the most popular install only a single carbon rather than uniting larger fragments. These methods are useful, but they are limited by harsh conditions or the need to prepare reagents. Introduced herein is the first catalytic method to prepare carbon carbon triple bonds from precursors that do not contain such linkages. By coupling benzaldehyde and benzyl chloride derivatives under basic conditions with an organocatalyst, good yields of alkynes are obtained. The catalyst, a highly reactive sulfenate anion, is readily generated under the reaction conditions from air-stable precursors. This method represents an attractive organocatalytic alternative to well-established stoichiometric approaches to alkynes and to transition-metal-based alkyne functionalization methods in various applications.