3-(benzo[b]thiophen-2-yl)-3-oxopropanenitrile | 1249556-86-2

• 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: 3-(benzo[b]thiophen-2-yl)-3-oxopropanenitrile
• 英文别名: 3-(1-Benzothiophen-2-yl)-3-oxopropanenitrile
• CAS: 1249556-86-2
• 化学式: C₁₁H₇NOS
• mdl: MFCD14660419
• 分子量: 201.249
• InChiKey: JBFQOOFQRGZKRF-UHFFFAOYSA-N

物化性质

• 沸点：
  411.1±25.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(benzo[b]thiophen-2-yl)-3-oxopropanenitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以48%的产率得到3-(benzo[b]thiophen-2-yl)-1H-pyrazol-5-amine
  参考文献：
  名称：

  Combining structure- and property-based optimization to identify selective FLT3-ITD inhibitors with good antitumor efficacy in AML cell inoculated mouse xenograft model

  摘要：

  FLT3 mutation is among the most common genetic mutations in acute myeloid leukemia (AML), which is also related with poor overall survival and refractory in AML patients. Recently, FLT3 inhibitors have been approved for AML therapy. Herein, a series of new compounds with pyrazole amine scaffold was discovered, which showed potent inhibitory activity against FLT3-ITD and significant selectivity against both FLT3-ITD and AML cells expressing FLT3-ITD. Compound 46, possessing the most promising cellular activity, blocked the autophosphorylation of FLT3 pathway in MV4-11 cell line. Furthermore, the apoptosis and downregulation of P-STAT5 were also observed in tumor cells extracted from the MV411 cell xenografts model upon compound 46 treatment. Compound 46 was also metabolically stable in vitro and suppressed tumor growth significantly in MV4-11 xenografts model in vivo. Compound 46 showed no toxicity to the viscera of mice and caused no decrease in body weight of mice. In conclusion, the results of this study could provide valuable insights into discovery of new FLT3 inhibitors, and compound 46 was worthy of further development as potential drug candidate to treat AML (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.021
• 作为产物：
  描述：

  甲基苯并噻吩-2-甲醛 、 乙腈 在 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 反应 24.0h， 以65%的产率得到3-(benzo[b]thiophen-2-yl)-3-oxopropanenitrile
  参考文献：
  名称：

  SeO2介导的3-氧-3-芳基丙腈和取代的乙醛一锅合成3-氰呋喃

  摘要：

  建立了一种通过SeO 2介导的3-氧代-3-芳基丙腈和乙醛环化在一个锅中合成3-氰呋喃的方法。探索了反应的一般性，并提出了一个合理的机制。

  DOI：

  10.1002/ejoc.201700383

文献信息

• Synthesis of Polysubstituted Phenols by Rhodium‐Catalyzed C−H/Diazo Coupling and Tandem Annulation
  作者：Min Liu、Kelu Yan、Jiangwei Wen、Xue Li、Xiaoyu Wang、Fengjie Lu、Xiu Wang、Hua Wang

  DOI：10.1002/adsc.202001456

  日期：2021.3.29

  rhodium(III)‐catalyzed C−H/diazo coupling and tandem annulation of 3‐oxopent‐4‐enenitriles have been proposed for the synthesis of polysubstituted phenols. Most products of phenols are obtained in good yields. Several preliminary mechanistic studies and derivatization reactions of phenol products were also performed. This method offers an alternative approach for the synthesis of useful diverse phenols.

  有人提出了铑（III）催化的CH /重氮偶合和3-氧杂戊-4-烯腈的串联环化反应，用于合成多取代的苯酚。大多数苯酚产品均以高收率获得。还进行了一些苯酚产物的初步机理研究和衍生化反应。该方法为合成有用的多种酚提供了另一种方法。
• Palladium-Catalyzed Carbonylative α-Arylation of <i>tert</i>-Butyl Cyanoacetate with (Hetero)aryl Bromides
  作者：Mikkel T. Jensen、Martin Juhl、Dennis U. Nielsen、Mikkel F. Jacobsen、Anders T. Lindhardt、Troels Skrydstrup

  DOI：10.1021/acs.joc.5b02897

  日期：2016.2.19

  A three-component coupling protocol has been developed for the generation of 3-oxo-3-(hetero)arylpropanenitriles via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions such as MgCl2 and

  已开发出一种三组分偶联方案，用于通过羰基钯催化的2-氰基乙酸叔丁酯与（杂）芳基溴化物的羰基钯催化的α-芳基化反应，生成3-氧代-3-（杂）芳基丙腈。介导的脱羧步骤。通过仅化学计量的一氧化碳负载量和适度的碱性反应条件（例如MgCl 2和二环己基甲胺）用于去质子化步骤，可以确保该方法具有出色的官能团耐受性。通过使用13 COgen生成的13 C标记的一氧化碳，相应的13获得了C-同位素标记的β-乙腈，这些产物随后可以通过位点特异性13 C-同位素标记转化为氰基炔烃和3-氰基苯并呋喃。
• Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles
  作者：Ge Zeng、Jichao Liu、Yinlin Shao、Fangjun Zhang、Zhongyan Chen、Ningning Lv、Jiuxi Chen、Renhao Li

  DOI：10.1021/acs.joc.0c02388

  日期：2021.1.1

  A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures

  已经开发出一种实用，方便且高度选择性的方法，该方法是由Pd催化的向二腈中添加有机硼试剂而合成β-酮腈。该方法提供了优异的官能团耐受性，广泛的基材范围以及使用市售基材的便利性。该方法有望在未来的合成程序中显示出更多的实用性。
• Process for reducing 3-heteroaryl-3-oxopropionic acid derivatives
  申请人：——

  公开号：US20030225274A1

  公开（公告）日：2003-12-04

  The present invention relates to a process for preparing stereoisomerically enriched 3-heteroaryl-3-hydroxycarboxylic esters by reducing 3-heteroaryl-3-oxocarboxylic esters in the presence of ruthenium-containing catalysts.

  本发明涉及一种在含有钌催化剂的情况下还原3-杂环基-3-酮羧酸酯以制备立体异构富集的3-杂环基-3-羟基羧酸酯的方法。
• One-pot synthesis of dual-state emission (DSE) luminogens containing the V-shape furo[2,3-b]furan scaffold
  作者：Jie Zhou、Manna Huang、Xinhai Zhu、Yiqian Wan

  DOI：10.1016/j.cclet.2020.02.038

  日期：2021.1

  Abstract To discover novel fluorophores of solution and solid dual-state emission (DSE) materials, unique V-shape furo[2,3-b]furans have been designed and synthesized by a one-pot method for the first time and their photoluminescent properties have been explored in benzene, THF, DMF and DMSO, as well as in the solid state. As the best example, 2,5-bis(4-(9H-carbazol-9-yl)phenyl)-6a-amino-3a,6a-dihydrofuro[2

  摘要为发现溶液和固态双态发射（DSE）材料的新型荧光团，首次通过一锅法设计并合成了独特的V型呋喃[2,3-b]呋喃及其光致发光性能。已在苯，THF，DMF和DMSO以及固态中进行了研究。最好的例子是2,5-双（4-（9H-咔唑-9-基）苯基）-6a-氨基-3a，6a-二氢呋喃[2,3-b]呋喃-3,3a，4-三碳腈（3g）在THF，苯和固态下表现出溶液和固体DSE性质，量子产率分别为55％，92％和45％。