3-((4-nitrophenyl)ethynyl)thiophene | 1362419-31-5

• 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: 3-((4-nitrophenyl)ethynyl)thiophene
• 英文别名: 3-(2-(4-nitrophenyl)ethynyl)thiophene；3-[2-(4-Nitrophenyl)ethynyl]thiophene
• CAS: 1362419-31-5
• 化学式: C₁₂H₇NO₂S
• 分子量: 229.259
• InChiKey: QVLYMMRMFSKYOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚 、 3-((4-nitrophenyl)ethynyl)thiophene 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以69%的产率得到(Z)-2-methyl-5-(2-(4-nitrophenyl)-1-(thiophene-3-yl)vinyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  底物控制的炔烃加氢胺化反应合成的（Z）-和（E）-N-苯乙烯基咔唑，氮杂咔唑和γ-咔啉的区域和立体选择性合成

  摘要：

  我们在本文中报告了在KOH / DMSO系统中，咔唑，氮杂咔唑和γ-咔啉与官能化的芳香族以及脂肪族炔烃进行底物控制的区域和立体选择性加氢胺化反应，产率很高。基材的电子效应决定着产品的立体化学。给电子炔烃提供（Z）-立体选择性产物，而吸电子炔烃提供（E）-立体选择性产物。这种方法也为合成单-和双-氢化胺化产物提供了简便的途径。还进行了氘标记研究以支持机理途径。

  DOI：

  10.1021/acs.joc.8b01642
• 作为产物：
  描述：

  3-乙炔基噻吩 、 4-硝基碘苯 在 四氢吡咯 、 C₇₀H₄₀Cl₂F₆₈N₂O₆Pd₂ 作用下， 以 水 为溶剂， 反应 0.2h， 以92%的产率得到3-((4-nitrophenyl)ethynyl)thiophene
  参考文献：
  名称：

  Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium

  摘要：

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.

  DOI：

  10.1021/jo202482h

文献信息

• Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium
  作者：Woen Susanto、Chi-Yuan Chu、Wei Jie Ang、Tzyy-Chao Chou、Lee-Chiang Lo、Yulin Lam

  DOI：10.1021/jo202482h

  日期：2012.3.16

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.
• Substrate-Controlled Regio- and Stereoselective Synthesis of (<i>Z</i>)- and (<i>E</i>)-<i>N</i>-Styrylated Carbazoles, Aza-carbazoles, and γ-Carbolines via Hydroamination of Alkynes
  作者：Vineeta Garg、Pradeep Kumar、Akhilesh K. Verma

  DOI：10.1021/acs.joc.8b01642

  日期：2018.10.5

  substrate-controlled regio- and stereoselective hydroamination of carbazoles, aza-carbazoles, and γ-carbolines with functionalized aromatic as well as aliphatic alkynes in a KOH/DMSO system in good yields. The electronic effect of the substrates governs the stereochemistry of the product. Electron-donating alkynes provided (Z)-stereoselective products, and electron-withdrawing alkynes provided (E)-stereoselective

  我们在本文中报告了在KOH / DMSO系统中，咔唑，氮杂咔唑和γ-咔啉与官能化的芳香族以及脂肪族炔烃进行底物控制的区域和立体选择性加氢胺化反应，产率很高。基材的电子效应决定着产品的立体化学。给电子炔烃提供（Z）-立体选择性产物，而吸电子炔烃提供（E）-立体选择性产物。这种方法也为合成单-和双-氢化胺化产物提供了简便的途径。还进行了氘标记研究以支持机理途径。