2-氰基甲基-1-乙炔基苯 | 1000512-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氰基甲基-1-乙炔基苯
• 英文名称: 2-(2-ethynylphenyl)acetonitrile
• CAS: 1000512-52-6
• 化学式: C₁₀H₇N
• mdl: MFCD09923791
• 分子量: 141.172
• InChiKey: VDVFSYRSXPIWFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-氰基甲基-1-乙炔基苯 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以95%的产率得到2-(2-(Bromoethynyl)phenyl)acetonitrile
  参考文献：
  名称：

  Synthesis of ortho-Diamino-Functionalized 1-Arylnaphthalenes through Nickel-Catalyzed Cyclization of Ynamide-Benzylnitriles with Organoboronic Acids

  摘要：

  DOI：

  10.1021/acs.orglett.1c02957
• 作为产物：
  描述：

  邻溴氰苄 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.58h， 生成 2-氰基甲基-1-乙炔基苯
  参考文献：
  名称：

  Synthesis of ortho-Diamino-Functionalized 1-Arylnaphthalenes through Nickel-Catalyzed Cyclization of Ynamide-Benzylnitriles with Organoboronic Acids

  摘要：

  DOI：

  10.1021/acs.orglett.1c02957

文献信息

• Metal-Free Synthesis of (<i>E</i>)-Monofluoroenamine from 1-Sulfonyl-1,2,3-triazole and Et₂O·BF₃ via Stereospecific Fluorination of α-Diazoimine
  作者：Ze-Feng Xu、Haican Dai、Lihong Shan、Chuan-Ying Li

  DOI：10.1021/acs.orglett.7b04014

  日期：2018.2.16

  general, stereospecific, and straightforward method for the rapid preparation of functionalized (E)-monofluoroenamines is reported. Rather than transition metals (Rh, Ni, Pd, Cu, Ag, etc.), Et2O·BF3 was employed to promote the formation of α-diazoimine through the Dimroth equilibrium of common 1-sulfonyl-1,2,3-triazole for the first time. An overall migration of fluoride from boron to the diazo-linked carbon

  报道了用于快速制备官能化的（E）-单氟烯胺的通用，立体定向和直接的方法。除了使用过渡金属（Rh，Ni，Pd，Cu，Ag等）以外，还使用Et 2 O·BF 3通过常见的1-磺酰基-1,2,3的Dimroth平衡促进α-重氮亚胺的形成。 -三唑首次。实现了氟化物从硼到α-重氮亚胺的重氮连接的碳的整体迁移。进行了生物活性分子的衍生和后期修饰。还提出了一个合理的机制。
• Palladium(II)-Catalyzed Cascade Reactions of Ene–Ynes Tethered to Cyano/Aldehyde: Access to Naphtho[1,2-<i>b</i>]furans and Benzo[<i>g</i>]indoles
  作者：Moumita Jash、Sukanya De、Subhendu Pramanik、Chinmay Chowdhury

  DOI：10.1021/acs.joc.9b00861

  日期：2019.7.19

  cyano/aldehyde group is described. It involves successive hetero- and benz-annulations in one pot via trans-oxo/aminopalladation onto alkyne, followed by 1,2-addition to cyano/aldehyde, providing a convenient synthesis of both naphtho[1,2-b]furans and benzo[g]indoles. The reaction constitutes a fast intramolecular assembly through several carbon–carbon and carbon–heteroatom bond formations taking place

  描述了一种有效的钯（II）催化带有氰基/醛基的烯炔基的级联反应。它涉及在一个锅中通过反式-羰基/氨基palpalation到炔烃上的连续异环和苯环，然后将1，2-加成到氰基/醛中，从而方便地合成萘并[1,2- b ]呋喃和苯并[ g ]吲哚。该反应通过一个罐中发生的数个碳-碳和碳-杂原子键构成了一种快速的分子内组装。该反应操作简单，与一系列官能团相容并且本质上是原子经济的。
• Synthesis of two nitrogen-containing polyaromatic compounds through gold catalysis/DBU-promoted cyclizations
  作者：Vikas Ashokrao Sadaphal、Tien-Lin Wu、Rai-Shung Liu

  DOI：10.1039/d4cc00113c

  日期：2024.4.16

  This work reports an efficient synthesis of novel benzo[7,8]indolizino[2,3,4,5-ija]quinazoline derivatives between 2-(2-ethynylaryl)acetonitriles 1 and anthranils 2. The synthetic approach involves the initial formation of 7-formylindole intermediates that can be implemented by DBU to activate a novel indole–nitrile–aldehyde cyclization.

  这项工作报道了一种新型苯并[7,8]吲嗪并[2,3,4,5- ija ]喹唑啉衍生物在2-(2-乙炔基芳基)乙腈1和邻氨基苯酚2之间的有效合成。合成方法涉及初始形成7-甲酰基吲哚中间体，可通过 DBU 来激活新型吲哚-腈-醛环化。
• 10.1021/acs.orglett.4c02443
  作者：Wang, Xing-Zhen、Huang, Hong-Gui、Liu, Wen-Bo

  DOI：10.1021/acs.orglett.4c02443

  日期：——

  metal-catalyzed [2 + 2 + 2] cycloaddition of nitriles and two alkynes is an efficient method for assembling pyridines. However, examples employing palladium catalysis have rarely been disclosed, and the processes of reactivity and selectivity remain unclear. We report here a palladium/copper dual metal-catalyzed [2 + 2 + 2] cycloaddition of diynyl-tethered malononitriles and terminal alkynes to synthesize

  过渡金属催化的腈和两个炔的[2+2+2]环加成是组装吡啶的有效方法。然而，采用钯催化的例子很少被公开，并且反应性和选择性的过程仍不清楚。我们在这里报道了二炔基丙二腈和末端炔烃的钯/铜双金属催化的[2 + 2 + 2]环加成反应来合成密集取代的吡啶。该方法具有良好的底物范围、综合有效产率和完美的区域选择性。吡啶产物的衍生化证明了该方法在合成杂环和作为光催化配体方面的潜在应用。初步机理研究表明，该反应经历了Pd(0)与腈和炔的氮杂氧化环加成，然后进行炔插入和还原消除。铜的存在对其反应性和区域选择性至关重要。
• Discovery of Potent and Orally Bioavailable GPR40 Full Agonists Bearing Thiophen-2-ylpropanoic Acid Scaffold
  作者：He Li、Qi Huang、Cheng Chen、Bin Xu、He-Yao Wang、Ya-Qiu Long

  DOI：10.1021/acs.jmedchem.6b01357

  日期：2017.4.13

  The free fatty acid receptor GPR40 is predominantly expressed in pancreatic beta-cells and enhances insulin secretion in a glucose dependent manner. Therefore, GPR40 agonists are possible novel insulin secretagogues with reduced or no risk of hypoglycemia for the treatment of type 2 diabetes mellitus (T2DM). Chemically and structurally diverse GPR40 agonists with high safety are pursued for the clinical development of GPR40-based pharmacotherapeutics. Herein we report our design and discovery of a new chemotype of GPR40 agonists free of the typical phenylpropanoic acid scaffold. The thiophen-2-ylpropanoic acid containing GPR40 modulators functioned as full agonists with high-efficacy response (E-max) and reduced lipophilicity. Significantly, the lead compound in this series, (R)-7k, exhibited more potent in vitro glucose-stimulated insulin secretion and in vivo glucose-lowering effects (10 mg/kg, po) than the GPR40 partial agonist TAK-875, which was once in phase III clinical trials, and high selectivity over the relevant receptors GPR120 and PPAR gamma.