N-phenyl-2-(thiophen-2-yl)acetamide | 69047-40-1

• 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-phenyl-2-(thiophen-2-yl)acetamide
• 英文别名: N-phenyl-2-(2-thienyl)acetamide；N-phenyl-2-thiophen-2-ylacetamide
• CAS: 69047-40-1
• 化学式: C₁₂H₁₁NOS
• mdl: MFCD00969575
• 分子量: 217.291
• InChiKey: OZAZJRGTYBNVMJ-UHFFFAOYSA-N

物化性质

• 溶解度：
  >32.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenyl-2-(thiophen-2-yl)acetamide 在 四丁基硫酸氢铵 、 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以44%的产率得到2-oxo-N-phenyl-2-(thiophen-2-yl)acetamide
  参考文献：
  名称：

  通过酰胺的需氧苄氧化直接合成N-单取代的α-酮酰胺

  摘要：

  描述了一种有效的碳酸氢钠促进的需氧氧化反应，以在正丁基硫酸氢铵（TBAHS）存在下制备N-单取代的α-酮酰胺。该反应提供了一种非常简单和方便的合成路线，可以容易地从芳基或杂芳基乙酰胺以高产率到高产率合成N-单取代的α-酮酰胺，而无需使用有毒试剂和苛刻的条件。

  DOI：

  10.1016/j.tet.2011.11.005
• 作为产物：
  描述：

  2-Benzotriazol-1-yl-N-phenyl-2-thiophen-2-yl-acetamide 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以59%的产率得到N-phenyl-2-(thiophen-2-yl)acetamide
  参考文献：
  名称：

  Efficient Syntheses of 2-Functionalized Thiophenes, Cyclopent[b]thiophenes, and Polysubstituted Benzo[b]thiophenes from 2-(Benzotriazol-1-ylmethyl)thiophenes

  摘要：

  Diverse 2-(functionalized-alkyl)- and 2-alkenylthiophenes 2a,b, 4a,b, and 6a-d are prepared via the side chain elaboration of 2-(benzotriazol-1-ylmethyl)thiophenes 3a,b, themselves readily available from the condensation of 1-(hydroxymethyl)benzotriazole with thiophenes 1a,b. Treatment of 2-(benzotriazol-1-ylmethyl)thiophenes 3b and 5gj with styrenes in the presence of zinc bromide results in formal [3 + 2] cycloaddition to give in good yields substituted cyclopent[b]thiophenes 16a/17a, 16b/17b, and 18. Lithiation and 1,4-addition to a variety of alpha,beta-unsaturated ketones and aldehydes, and subsequent acid-catalyzed intramolecular cyclization followed by debenzotriazolylation-dehydration converts 3 and 5 to a range of polysubstituted benzo[b]thiophenes 19a-d and 25a-e in moderate to excellent yields. NOE difference spectroscopy and NMR H-1-C-13 long-range correlation support structures of types 19 and 25 and exclude those of type 26, thus confirming the cyclization pathway.

  DOI：

  10.1021/jo970672g

文献信息

• Deoxygenative Hydrogenation of Amides Catalyzed by a Well-Defined Iridium Pincer Complex
  作者：Ming-Lei Yuan、Jian-Hua Xie、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1021/acscatal.6b01019

  日期：2016.6.3

  The iridium-catalyzed highly chemoselective hydrogenation of amides to amines has been developed. Using a well-defined iridium catalyst bearing a P(O)C(O)P pincer ligand combined with B(C6F5)3, the C–O cleavage products are formed under mild reaction conditions. The reaction provides a new method for the preparation of amines from amides in good yield with high selectivity.

  已经开发了铱催化的酰胺高度化学选择性氢化成胺的方法。使用带有P（O）C（O）P钳形配体与B（C 6 F 5）3结合的明确定义的铱催化剂，在温和的反应条件下可形成C–O裂解产物。该反应提供了一种以高收率和高选择性从酰胺制备胺的新方法。
• Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines
  作者：Ming-Lei Yuan、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1002/cctc.201600635

  日期：2016.10.6

  The hydrogenation of amides to amines has been developed by using the catalyst [Ru(H)2(CO)(Triphos)] (Triphos=1,1,1‐tri(diphenylphosphinomethyl)ethane) and catalytic boron Lewis acids such as B(C6F5)3 or BF3⋅Et2O as additives. The reaction provides an efficient method for the preparation of secondary amines from amides in good yields with high selectivity.

  已通过使用催化剂[Ru（H）2（CO）（Triphos）]（Triphos = 1,1,1,1-tri（diphenylphosphinomethyl）ethane）和催化硼路易斯酸（例如B（ ç 6 ˚F 5）3或BF 3 ⋅的Et 2 O作为添加剂。该反应提供了以高收率和高选择性从酰胺制备仲胺的有效方法。
• Process for the activation of carboxylic acids
  申请人：Antibioticos, S.A.

  公开号：US04230849A1

  公开（公告）日：1980-10-28

  A process for the activation of carboxylic acids which is useful for the subsequent conversion of said carboxylic acids into their corresponding amides or esters, based on reacting a 2-oxazolidinone with phosphorus pentachloride and subsequent addition of a salt of the carboxylic acid to be activated.

  一种用于激活羧酸的方法，可用于将这些羧酸转化为相应的酰胺或酯，其基于将2-噁唑烷酮与五氯化磷反应，并随后添加待激活的羧酸盐。
• Carboxamides as <i>N</i> -Alkylating Reagents of Secondary Amines in Indium-Catalyzed Reductive Amination with a Hydrosilane
  作者：Yohei Ogiwara、Wataru Shimoda、Keisuke Ide、Takumi Nakajima、Norio Sakai

  DOI：10.1002/ejoc.201601629

  日期：2017.5.26

  N-alkylation of amines by using secondary amides as the alkyl source was developed. A versatile type of carboxamide functioned as an N-alkylation reagent in the presence of an indium(III) catalyst and a hydrosilane to provide alkylated tertiary amines efficiently. This amide-based catalytic N-alkylation strategy is considered to be a highly useful protocol to access unsymmetrical tertiary amines.

  开发了一种以仲酰胺为烷基源催化还原N-烷基化胺的方法。在铟 (III) 催化剂和氢硅烷的存在下，一种多功能的甲酰胺可用作 N-烷基化试剂，以有效地提供烷基化叔胺。这种基于酰胺的催化 N-烷基化策略被认为是获取不对称叔胺的非常有用的方案。
• Photoinduced Carbamoylation of C(sp³)–H Bonds with Isocyanates
  作者：Tairin Kawasaki、Katsushi Yamazaki、Ryota Tomono、Naoki Ishida、Masahiro Murakami

  DOI：10.1246/cl.210333

  日期：2021.9.5

  isocyanates at the benzylic position upon irradiation with visible light in the presence of an iridium photoredox catalyst, a bromide anion, and a nickel catalyst, producing N-substituted α-aryl amides. An analogous carbamoylation reaction of aliphatic C–H bonds of alkanes took place when UV light and a diaryl ketone were used instead of visible light and the iridium complex. The present reaction offers

  在铱光氧化还原催化剂、溴化物阴离子和镍催化剂存在下，在可见光照射下，烷基苯与苄基位置的异氰酸酯偶联，生成N-取代的 α-芳基酰胺。当使用紫外光和二芳基酮代替可见光和铱络合物时，烷烃的脂肪族 C-H 键发生类似的氨基甲酰化反应。本反应提供了一种直接且原子经济的方法，用于从具有单碳延伸的碳氢化合物开始合成羧酰胺。