N-乙基-苯乙酰胺 | 5465-00-9

• 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: N-乙基-苯乙酰胺
• 英文名称: N-ethylphenylacetamide
• 英文别名: α-ethyl-benzeneacetamide；N-ethyl-2-phenylacetamide；N-ethyl phenylacetamide；phenylacetylaminoethane；phenyl-acetic acid ethylamide；Phenyl-essigsaeure-aethylamid
• CAS: 5465-00-9
• 化学式: C₁₀H₁₃NO
• mdl: MFCD01182773
• 分子量: 163.219
• InChiKey: QDHFDXDMKYJPSC-UHFFFAOYSA-N

物化性质

• 熔点：
  75 °C
• 沸点：
  340.3±21.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)
• 保留指数：
  1511

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-乙基-苯乙酰胺 在 氧气 、 palladium diacetate 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 2,2,2-三氟乙醇 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以87%的产率得到N-ethyl-2-(2'-((ethylcarbamoyl)methyl)biphenyl-2-yl)acetamide
  参考文献：
  名称：

  Oxidative C–H Homodimerization of Phenylacetamides

  摘要：

  A range of secondary and tertiary phenylacetamides undergo oxidative homodimerization to afford biaryls. The reaction proceeds under palladium catalysis in the presence of a copper cocatalyst and oxygen and is most effective for electron-rich substrates.

  DOI：

  10.1021/ol202212f
• 作为产物：
  描述：

  2-benzyl-2-(methoxymethoxy)malononitrile 在 四氢吡咯 、 左旋樟脑磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 N-乙基-苯乙酰胺
  参考文献：
  名称：

  通过与MAC试剂的Mitsunobu反应将伯醇单碳同化为羧酸，酯和酰胺

  摘要：

  报道了一种方法，将醇与扩展的羧酸，酯或酰胺进行单碳同系化。该方法涉及与烷氧基丙二腈的Mitsunobu反应，然后在合适的亲核试剂存在下进行掩蔽。同源和解掩蔽甚至可以一锅法高产率进行。

  DOI：

  10.1021/acs.orglett.6b00790

文献信息

• COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF INTERLEUKIN-1 RECEPTOR-ASSOCIATED KINASE 4 POLYPEPTIDES
  申请人：Arvinas, Inc.

  公开号：US20190151295A1

  公开（公告）日：2019-05-23

  The present disclosure relates to bifunctional compounds, which find utility as modulators of Interleukin-1 Receptor-Associated Kinase 4 (IRAK-4); the target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hppel-Lindau, cereblon, ligand which binds to the E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

  本公开涉及双功能化合物，其作为白细胞介素-1受体相关激酶4（IRAK-4；目标蛋白）的调节剂具有实用性。具体而言，本公开涉及包含一端结合E3泛素连接酶的Von Hppel-Lindau、cereblon配体的双功能化合物，另一端结合目标蛋白的部分，使得目标蛋白靠近泛素连接酶以实现目标蛋白的降解（和抑制）。本公开展示了与目标蛋白的降解/抑制相关的广泛药理活性。本公开的化合物和组合物用于治疗或预防由目标蛋白聚集或积累导致的疾病或紊乱。
• The Selective<i>N</i>-Monoalkylation of Amides with Alkyl Halides in the Presence of Alumina and KOH
  作者：Kazuaki Sukata

  DOI：10.1246/bcsj.58.838

  日期：1985.3

  The effects of alumina impregnated with KOH (KOH/Al2O3) and a mixture of alumina and powdered KOH (KOH+Al2O3) have been examined using the alkylation of benzamide under various conditions. In each case, alkylation occurs exclusively in the pores of the alumina, the extent depending upon the alumina-pore size. For both yield and selectivity for N-monoalkylation, KOH+Al2O3 is superior to KOH/Al2O3. Dioxane is the best of the solvents employed. It is proposed that, in dioxane, an enolate-like species, (Remark: Graphics omitted.), exists as stable ion-pair aggregates, which are the true reactants in the pore. This method, using KOH/Al2O3 or KOH+Al2O3, has been applied to N-alkylation of the other amides, giving the N-monoalkylated products in substantial yields with extremely high selectivities. 2-Phenylacetamide is regioselectively N-monoalkylated in high yields. This regioselectivity is explained in terms of steric hindrance.

  使用KOH浸渍的氧化铝（KOH/Al2O3）和氧化铝与粉末状KOH的混合物（KOH+Al2O3），在不同条件下研究了苯甲酰胺的烷基化反应。在每种情况下，烷基化反应仅在氧化铝的孔隙中发生，其程度取决于氧化铝的孔径大小。对于N-单烷基化的产率和选择性，KOH+Al2O3优于KOH/Al2O3。二氧六环是所使用溶剂中最好的。研究表明，在二氧六环中，类似于烯醇盐的物种（注：图形省略）以稳定的离子对聚集形式存在，这些是孔隙中的真正反应物。这种方法使用KOH/Al2O3或KOH+Al2O3，已应用于其他酰胺的N-烷基化，以极高的选择性获得了大量的N-单烷基化产物。2-苯基乙酰胺以高产率选择性地进行N-单烷基化。这种区域选择性可通过空间位阻来解释。
• Solvent-Free N-Alkylation of Amides with Alcohols Catalyzed by Nickel on Silica-Alumina
  作者：Aubin Charvieux、Louis Le Moigne、Lorenzo G. Borrego、Nicolas Duguet、Estelle Métay

  DOI：10.1002/ejoc.201901291

  日期：2019.10.31

  To date, the N‐alkylation of amides with alcohols has not been studied with non‐noble metal base heterogeneous catalyst. Herein, a range of amide was efficiently N‐alkylated with various alcohols using cheap and easy to handle Ni/SiO2‐Al2O3.

  迄今为止，尚未使用非贵金属碱多相催化剂研究酰胺与醇的N-烷基化。在此，使用廉价且易于处理的Ni / SiO 2 -Al 2 O 3将各种酰胺有效地与各种醇进行N-烷基化。
• The Ruthenium Catalyzed<i>N</i>-Alkylation of Amides with Alcohols
  作者：Yoshihisa Watanabe、Tetsuo Ohta、Yasushi Tsuji

  DOI：10.1246/bcsj.56.2647

  日期：1983.9

  Amides reacted with primary alcohols in the presence of a catalytic amount of RuCl2(PPh3)3 at 180 °C to give the corresponding N-monoalkyl amides in fairly good yields. Thus, benzamide reacted with 1-octanol to give N-octylbenzamide in 76% yield with excellent product selectivity. Little esterification of amides with alcohols occurred and selectivity to the N-alkylation was high. Most of the amides gave N-monoalkyl amides but no N,N-dialkyl amides. But formamide reacted with 1-butanol to give N,N-dibutylformamide, as well as N-butylformamide, in low yield. RuCl2(PPh3)3 was the most effective catalyst for this reaction and RuHCl(PPh3)3 also had some catalytic activity.

  在180°C下，酰胺与伯醇在催化量的RuCl2(PPh3)3存在下反应，得到相应的一烷基化酰胺，产率相当好。因此，苯甲酰胺与1-辛醇反应，以76%的产率得到N-辛基苯甲酰胺，且产品选择性极佳。酰胺与醇的酯化反应很少发生，N-烷基化的选择性很高。大多数酰胺得到的是一烷基化酰胺，而不是N,N-二烷基化酰胺。但甲酰胺与1-丁醇反应，以低产率生成N,N-二丁基甲酰胺以及N-丁基甲酰胺。RuCl2(PPh3)3是该反应最有效的催化剂，而RuHCl(PPh3)3也具有一定的催化活性。
• PROCESS FOR ALKENYLATING CARBOXAMIDES
  申请人：Staffel Wolfgang

  公开号：US20090131657A1

  公开（公告）日：2009-05-21

  The present invention relates to a process for preparing N-(1-alkenyl)carboxamides of the formula I, which comprises reacting a carboxamide of the formula II with an alkyne of the formula III in the presence of a catalyst selected from among carbonyl complexes, halides and oxides of rhenium, manganese, tungsten, molybdenum, chromium and iron.

  本发明涉及一种制备式I的N-(1-烯基)羧酰胺的方法，包括在选择自铼、锰、钨、钼、铬和铁的羰基配合物、卤化物和氧化物之一作为催化剂的情况下，将式II的羧酰胺与式III的炔烃反应。