N,N-diethyl-2-butenamide | 35172-84-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N-diethyl-2-butenamide
• 英文别名: N,N-diethylbut-2-enamide
• CAS: 35172-84-0
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: TXHUHDDZTWDOAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  224 °C(Press: 756 Torr)
• 密度：
  0.890±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2-butenamide 在 sodium hydroxide 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 (E)-[5(2-diethylcarbamoyl-1-methylvinyl)-2-(1-phenyl-ethoxy)-phenyl]-acetic acid
  参考文献：
  名称：

  Carboxy-Substituted Cinnamides:  A Novel Series of Potent, Orally Active LTB₄ Receptor Antagonists

  摘要：

  A series of carboxy-substituted cinnamides were investigated as antagonists of the human cell surface leukotriene B-4 (LTB4) receptor. Binding was determined through measurement of [H-3]-LTB4 displacement from human neutrophils. Receptor antagonism was confirmed through a functional assay, which measures inhibition of Ca2+ release in human neutrophils. Potent antagonists were discovered through optimization of a random screening hit, a p-(alpha-methylbenzyloxy)cinnamide, having low-micromolar activity. Substantial improvement of in vitro potency was realized by the attachment of a carboxylic acid moiety to the cinnamide phenyl ring through a flexible tether, leading to identification of compounds with low-nanomolar potency. Modification of the benzyloxy substituent, either through ortho-substitution on the benzyloxy phenyl group or through replacement of the ether oxygen with a methylene or sulfur atom, produced achiral antagonists of equal or greater potency. The most potent compounds in vitro were assayed for oral activity using the arachidonic acid-induced mouse ear edema model of inflammation. Several compounds in this series were found to significantly inhibit edema formation and myeloperoxidase activity in this model up to 17 h after oral administration. Representatives of this series have been shown to be potent and long-acting orally active inhibitors of the LTB4 receptor.

  DOI：

  10.1021/jm980540v
• 作为产物：
  描述：

  巴豆酸 、 diethyl-amidosulfurous acid methyl ester 在 吡啶 作用下， 生成 N,N-diethyl-2-butenamide
  参考文献：
  名称：

  Becker,H.G.O.; Funk,K.F., Journal fur praktische Chemie (Leipzig 1954), 1961, vol. 14, p. 55 - 59

  摘要：

  DOI：

文献信息

• Niobium Pentachloride Promoted Conversion of Carboxylic Acids to Carboxamides­: Synthesis of the 4-Aryl-1,2,3,4-tetrahydroisoquinoline Alkaloid­ Structures
  作者：Claudio C. Lopes、Rosangela S. Lopes、Marcelo S. Nery、Renata P. Ribeiro

  DOI：10.1055/s-2003-36823

  日期：——

  A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4'-methoxybenzyl)benzamide.

  描述了一种在温和条件下由五氯化铌介导的将羧酸转化为相应羧酰胺的实用方法。4-aryl-1,2,3,4-四氢异喹啉生物碱结构的合成是通过 N-methyl-3,4-dimethoxy-2-(4'-methoxybenzyl)benzamide 的苄基锂化完成的。
• Regioselective Radical Borylation of α,β-Unsaturated Esters and Related Compounds by Visible Light Irradiation with an Organic Photocatalyst
  作者：Guosong Li、Guanwang Huang、Ruixia Sun、Dennis P. Curran、Wen Dai

  DOI：10.1021/acs.orglett.1c01270

  日期：2021.6.4

  recently been reported and are still rare. Here we describe a photoredox radical hydroboration of α,β-unsaturated esters, amides, ketones, and nitriles with NHC-boranes that uses only an organocatalyst and visible light. The conditions are mild, the substrate scope is broad, and the α/β regioselectivity is high. The reaction requires only the organocatalyst; there is no costly metal, and there are no

  自由基硼氢化反应直到最近才被报道并且仍然很少见。在这里，我们描述了 α,β-不饱和酯、酰胺、酮和腈与 NHC-硼烷的光氧化还原自由基硼氢化反应，该反应仅使用有机催化剂和可见光。条件温和，底物范围广，α/β区域选择性高。该反应只需要有机催化剂；没有昂贵的金属，也没有其他添加剂（碱、助催化剂、引发剂）。
• Palladium-Catalyzed Double-Carbonylation of Alkenyl Halides with Secondary Amines To Give α-Keto Amides
  作者：Tae-il Son、Hisayoshi Yanagihara、Fumiyuki Ozawa、Akio Yamamoto

  DOI：10.1246/bcsj.61.1251

  日期：1988.4

  are successfully double-carbonylated under appropriate reaction conditions and the corresponding α-keto amides are obtained in good to modest yields together with amides. In contrast, the reactions of alkenyl halides without a phenyl group give amides exclusively. In order to clarify the reason for the substrate-specificity in the reaction, series of alkenyl- and alkenoylpalladium(II) complexes, the

  详细研究了在钯催化剂存在下烯基卤化物与二乙胺的双羰基化反应。该反应生成 α-酮酰胺和酰胺，即单羰基化副产物。α-酮酰胺的产率很大程度上取决于烯基卤化物的性质。在乙烯基上具有苯基作为取代基的烯基溴化物或碘化物在适当的反应条件下成功地双羰基化，并且与酰胺一起以良好至适中的产率获得相应的α-酮酰胺。相反，没有苯基的链烯基卤化物的反应仅产生酰胺。为了阐明反应中底物特异性的原因，一系列链烯基-和链烯酰基钯（II）配合物，催化反应中的假定中间体，已经制备并检查了它们与仲胺、一氧化碳和链烯基卤化物的反应。该研究表明，三种类型的pro的操作...
• Preparation of 2-, 3-, 4- and 7-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans and their BLT₁and/or BLT₂inhibitory activities
  作者：Kumiko Ando、Yoko Kawamura、Yukiko Akai、Jun-ichi Kunitomo、Takehiko Yokomizo、Masayuki Yamashita、Shunsaku Ohta、Takahiro Ohishi、Yoshitaka Ohishi

  DOI：10.1039/b710935k

  日期：——

  Several 2-alkylcarbamoyl-1-alkylvinylbenzo[b]furans were designed to find a selective leukotriene B4 (LTB4) receptor antagonist. 2-(2-Alkylcarbamoyl-1-alkylvinyl)benzo[b]furans having a substituent group at the 3-position, 4-(2-alkylcarbamoyl-1-methylvinyl)benzo[b]furans having a substituent group at the 3-position, and 7-(2-alkylcarbamoyl-1-methylvinyl)benzo[b]furans and 3-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans were prepared and evaluated for LTB4receptor (BLT1 and BLT2) inhibitory activities. (E)-3-Amino-4-[2-[2-(3,4-dimethoxyphenyl)ethylcarbamoyl]-1-methylvinyl]benzo[b]furan ((E)-17c) showed potent and selective inhibitory activity for BLT2. On the other hand, (E)-7-(2-diethylcarbamoyl-1-methylvinyl)benzo[b]furan ((E)-27a) showed potent inhibitory activity for both BLT1 and BLT2.

  设计了几种2-烷基氨基甲酰基-1-烷基乙烯基苯并[b]呋喃，旨在寻找选择性的白三烯B4（LTB4）受体拮抗剂。合成了在3-位具有取代基的2-(2-烷基氨基甲酰基-1-烷基乙烯基)苯并[b]呋喃、在3-位具有取代基的4-(2-烷基氨基甲酰基-1-甲基乙烯基)苯并[b]呋喃、7-(2-烷基氨基甲酰基-1-甲基乙烯基)苯并[b]呋喃和3-(2-烷基氨基甲酰基-1-烷基乙烯基)苯并[b]呋喃，并评估了它们对LTB4受体（BLT1和BLT2）的抑制活性。(E)-3-氨基-4-[2-[2-(3,4-二甲氧基苯基)乙基氨基甲酰基]-1-甲基乙烯基]苯并[b]呋喃((E)-17c)显示出对BLT2具有强效且选择性的抑制活性。另一方面，(E)-7-(2-二乙基氨基甲酰基-1-甲基乙烯基)苯并[b]呋喃((E)-27a)对BLT1和BLT2均显示出强效的抑制活性。
• Cross-Coupling of Acrylamides and Maleimides under Rhodium Catalysis: Controlled Olefin Migration
  作者：Satyasheel Sharma、Sang Hoon Han、Yongguk Oh、Neeraj Kumar Mishra、Suk Hun Lee、Joa Sub Oh、In Su Kim

  DOI：10.1021/acs.orglett.6b00909

  日期：2016.6.3

  The rhodium(III)-catalyzed direct cross-coupling reaction of electron-deficient acrylamides with maleimides is described. This protocol displays broad functional group tolerance and high efficiency, which offers a new opportunity to access highly substituted succinimides. Dependent on the substituent positions of acrylamides and reaction conditions, olefin migrated products were obtained with high

  描述了缺电子的丙烯酰胺与马来酰亚胺的铑（III）催化的直接交叉偶联反应。该协议显示了广泛的官能团耐受性和高效率，这为获得高度取代的琥珀酰亚胺提供了新的机会。根据丙烯酰胺的取代基位置和反应条件，获得具有高区域选择性和立体选择性的烯烃迁移产物。