N-(1-phenylethyl)cyclopropanecarboxamide | 78172-92-6

• 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: N-(1-phenylethyl)cyclopropanecarboxamide
• CAS: 78172-92-6
• 化学式: C₁₂H₁₅NO
• mdl: MFCD03159450
• 分子量: 189.257
• InChiKey: NVEDNAPMXDKXSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙烯 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 三氟化硼乙醚 、 copper diacetate 、 1,4-双(二苯基膦)丁烷 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 1.0h， 生成 N-(1-phenylethyl)cyclopropanecarboxamide
  参考文献：
  名称：

  氧化亲核取代：烷基硼衍生物的转化

  摘要：

  本文描述了一种有效的酰胺化反应。在乙酸铜和三氟化硼的存在下，烷基三氟硼酸钾盐可从腈转化为酰胺。反应的延伸允许形成胺，醚和CC键。

  DOI：

  10.1016/j.tet.2011.09.055

文献信息

• One-Pot Synthesis of α-Branched <i>N</i>-Acylamines via Titanium-Mediated Condensation of Amides, Aldehydes, and Organometallics
  作者：Chunhui Dai、Julien Genovino、Bruce M. Bechle、Matthew S. Corbett、Chan Woo Huh、Colin R. Rose、Jianmin Sun、Joseph S. Warmus、David C. Blakemore

  DOI：10.1021/acs.orglett.7b00082

  日期：2017.3.3

  A three-component, titanium-mediated synthesis of α-branched N-acylamines from commercial or readily accessible amides, aldehydes, and organometallic reagents is reported. The transformation proceeds under mild reaction conditions and tolerates a variety of functional groups (including nitrile, carbamate, olefin, basic amine, furan, and other sensitive heteroaromatics) to generate a large umbrella

  报道了由市售或易于获得的酰胺，醛和有机金属试剂的三组分钛介导的α-支化N-酰基胺的合成。转化在温和的反应条件下进行，并能耐受各种官能团（包括腈，氨基甲酸酯，烯烃，碱性胺，呋喃和其他敏感的杂芳族化合物），从而以高收率生成大片的α-支化N-酰基胺产物。操作上实际可行的程序使该方法可用于并行化学合成中，这是一个有价值的功能，可以促进药物化学家对生物活性分子的筛选。
• Silica boron–sulfuric acid nanoparticles (SBSANs): preparation, characterization and their catalytic application in the Ritter reaction for the synthesis of amide derivatives
  作者：Ali Khalafi-Nezhad、Habib ollah Foroughi、Mohammad Mahdi Doroodmand、Farhad Panahi

  DOI：10.1039/c1jm11154j

  日期：——

  Among a number of different heterogeneous and homogeneous catalysts, silica boron–sulfuric acid nanoparticles (SBSANs) with both protic and Lewis acidic sites were shown to be the most active and recyclable catalyst in the Ritter reaction. Various amide derivatives were synthesized from alcohols and nitrilesvia a one-step and easy process in the presence of a catalytic amount of SBSAN at room temperature in solvent free conditions with excellent isolated yields. The silica boron–acid nanoparticles (SBANs) were regularly synthesized during the modification of the silica support by boric acid [B(OH)3] during the chemical vapor deposition (CVD) process and subsequently, this material was reacted with chlorosulfonic acid (ClSO3H) to obtain the SBSAN catalyst. The new catalyst was characterized using some different microscopic and spectroscopic techniques such as patterned X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), FT-Raman spectrometry and FT-IR spectroscopy. Thermal behavior of the SBSAN catalyst was also investigated by a thermogravimetric (TG) analyzer.

  在一系列不同的均相和非均相催化剂中，硅硼硫酸纳米粒子（SBSANs）由于同时具有质子酸和路易斯酸性位点，被证明是Ritter反应中最活跃且可循环使用的催化剂。通过一种简单的一步法过程，在无溶剂条件下，使用催化量的SBSANs并在室温下，从醇和腈合成了多种酰胺衍生物，分离产率极佳。硅硼酸纳米粒子（SBANs）是在化学气相沉积（CVD）过程中通过硼酸[B(OH)3]改性硅载体时定期合成的，随后，这种材料与氯磺酸（ClSO3H）反应以获得SBSAN催化剂。新催化剂通过一些不同的微观和光谱技术进行表征，如X射线衍射（XRD）、透射电子显微镜（TEM）、扫描电子显微镜（SEM）、傅里叶变换拉曼光谱和傅里叶变换红外光谱。SBSAN催化剂的热行为也通过热重（TG）分析仪进行了研究。
• A CONVENIENT METHOD FOR THE SYNTHESIS OF CARBOXAMIDES AND PEPTIDES BY THE USE OF TETRABUTYLAMMONIUM SALTS
  作者：Yutaka Watanabe、Teruaki Mukaiyama

  DOI：10.1246/cl.1981.285

  日期：1981.3.5

  aqueous THF with bis(o-nitrophenyl) phenylphosphonate in the presence of tetrabutylammonium hydrogen sulfate or bromide. Carboxylic esters are also successfully converted to amides via carboxylate salts in one-pot.

  在四丁基硫酸氢铵或溴化铵存在下，用双（邻硝基苯基）苯基膦酸酯处理 H2O-二氯甲烷或 THF 水溶液中的游离酸和胺，以良好的收率制备各种甲酰胺和肽。羧酸酯也可以通过羧酸盐在一锅法中成功转化为酰胺。
• ANTIVIRAL COMPOUNDS
  申请人：Gilead Pharmasset LLC

  公开号：EP3284741A1

  公开（公告）日：2018-02-21

  The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  本发明涉及抗病毒化合物、含有此类化合物的组合物、包括施用此类化合物的治疗方法，以及制备此类化合物的工艺和中间体。
• Ritter-type amidation of alkylboron derivatives with nitriles
  作者：Clément Cazorla、Estelle Métay、Bruno Andrioletti、Marc Lemaire

  DOI：10.1016/j.tetlet.2009.09.132

  日期：2009.12

  A mild and facile synthesis of amides from alkylboron compounds and nitriles promoted by copper acetate and BF3 center dot OEt2 at room temperature is disclosed. (C) 2009 Elsevier Ltd. All rights reserved.