N,N-dimethylbenzo[b]thiophene-3-carboxamide | 1075241-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N,N-dimethylbenzo[b]thiophene-3-carboxamide
• 英文别名: N,N-dimethyl-1-benzothiophene-3-carboxamide
• CAS: 1075241-14-3
• 化学式: C₁₁H₁₁NOS
• mdl: MFCD10661119
• 分子量: 205.28
• InChiKey: ISDUZANRQFOSOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethylbenzo[b]thiophene-3-carboxamide 在 正丁基锂 作用下， 以 hexanes 、 乙醚 为溶剂， 反应 1.0h， 以52%的产率得到dibenzo[d,d']benzo[1,2-b:4,5-b']dithiophene-6,12-dione
  参考文献：
  名称：

  WO2008/131835

  摘要：

  公开号：
• 作为产物：
  描述：

  3-溴苯并噻吩 、 二甲氨基甲酰氯 在 乙二醇二甲醚溴化镍 、 三(三甲基硅基)硅烷 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 4,4'-二叔丁基-2,2'-二吡啶 、 四甲基胍 作用下， 以 乙腈 为溶剂， 以72 %的产率得到N,N-dimethylbenzo[b]thiophene-3-carboxamide
  参考文献：
  名称：

  Photo‐Excited Nickel‐Catalyzed Silyl‐Radical‐Mediated Direct Activation of Carbamoyl Chlorides To Access (Hetero)aryl Carbamides**

  摘要：

  AbstractAmide bonds connect the amino acids in proteins and exist as a prevalent structural motif in biomolecules. Herein, we have exploited the concept of cross‐electrophile coupling by merging the photo‐redox and transition‐metal catalysis to construct carbamides from superabundant (hetero)aryl halides along with commercially feasible carbamoyl chlorides. The success of this method relies on the prior formation of NiII‐aryl halide intermediates, which involves in a photoexcited Ni‐halide homolysis event by energy transfer from aryl bromide and single‐electron transfer from aryl chloride to assist generation of the vital carbamoyl radical. The breadth of application of this technique is demonstrated both in inter‐ as well as intramolecular routes for the synthesis of a plethora of (hetero)aryl carbamides with diverse functionalities, and biologically important benzolactams.

  DOI：

  10.1002/anie.202207472

文献信息

• Direct and Selective C-H Carbamoylation of (Hetero)aromatics with TMSOTf-Activated Carbamoyl Chloride
  作者：Ayaka Uehara、Sandra Olivero、Bastien Michelet、Agnès Martin-Mingot、Sébastien Thibaudeau、Elisabet Duñach

  DOI：10.1002/ejoc.201801338

  日期：2019.1.10

  TMSOTf acts as Lewis acid to activate carbamoyl chlorides and generates highly electrophilic carbamoyl triflates in situ; these are active species for late‐stage aromatic carbamoylation.

  TMSOTf充当路易斯酸来激活氨基甲酰氯，并在原位生成高度亲电的氨基甲酰三氟甲磺酸酯；这些是晚期芳族氨基甲酰化的活性物种。
• Asymmetric Synthesis of Propargylic α-Stereogenic Tertiary Amines by Reductive Alkynylation of Tertiary Amides Using Ir/Cu Tandem Catalysis
  作者：Toolika Agrawal、Kimberly D. Perez-Morales、Jermaine A. Cort、Joshua D. Sieber

  DOI：10.1021/acs.joc.2c00131

  日期：2022.5.6

  The development of an asymmetric protocol for the reductive alkynylation of amides to access important α-stereogenic tertiary propargylic amines is reported using a tandem Ir-catalyzed hydrosilylation/enantioselective Cu-catalyzed alkynylation. The reaction utilizes a Cu/PyBox catalyst system in the alkynylation step to achieve asymmetry and affords excellent yields with moderate to good levels of

  据报道，使用串联 Ir 催化的氢化硅烷化/对映选择性 Cu 催化的炔基化，开发了一种不对称方案，用于酰胺的还原炔基化以获取重要的 α-立体异构叔炔丙基胺。该反应在炔基化步骤中使用 Cu/PyBox 催化剂体系来实现不对称性，并在使用低 Ir 催化剂负载量 (0.5 mol%) 的同时提供出色的产率和中等至良好的对映体控制水平。
• Rh^III-Catalyzed Synthesis of Cyclopenta[<i>b</i>]carbazoles via Cascade C–H/C–C Bond Cleavage and Cyclization Reactions: Using Amide as a Traceless Directing Group
  作者：Yanwei Wang、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.9b03969

  日期：2020.1.3

  Rhodium-catalyzed cascade C-H/C-C cleavage and cyclization reactions of 3-amide substituted indoles with diynes to construct cyclopenta[b]carbazoles have been developed. A strategy amide worked as a novel traceless directing group along with C-C bond cleavage via Friedel-Crafts-retro reaction has been disclosed in this protocol. This method exhibits a broad substrate scope and tolerates various functional

  已开发出铑催化的级联CH / CC裂解和3-酰胺取代的吲哚与二炔的环化反应，以构建环戊[b]咔唑。在该方案中已公开了一种策略酰胺，它作为一种新型的无痕导向基团，以及通过Friedel-Crafts-retro反应的CC键裂解。该方法显示出广泛的底物范围并耐受各种官能团，从而以良好或高收率提供了咔唑衍生物。
• Organic Semiconductors
  申请人：Heeney Martin

  公开号：US20100117066A1

  公开（公告）日：2010-05-13

  The invention relates to novel substituted dibenzo[d,d′]benzo[1,2-b;4,5-b′]dithiophenes (DBBDT), to methods of their synthesis, to organic semiconducting materials, formulations and layers comprising them, and to electronic devices, like organic field effect transistors (OFETs), comprising them.

  本发明涉及新颖的取代二苯并[d，d′]苯并[1,2-b;4,5-b′]二硫噻吩(DBBDT)，其合成方法，有机半导体材料，包含它们的配方和层，以及包含它们的电子器件，如有机场效应晶体管(OFETs)。
• ORGANIC SEMICONDUCTORS
  申请人：Merck Patent GmbH

  公开号：EP2139901A1

  公开（公告）日：2010-01-06