2-(4'-chlorophenyl)-benzo[b]thiophene-3-carboxaldehyde

• 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: 2-(4'-chlorophenyl)-benzo[b]thiophene-3-carboxaldehyde
• 英文别名: 2-(4-chlorophenyl)benzo[b]thiophene-3-carbaldehyde；2-(4-chlorophenyl)-1-benzothiophene-3-carbaldehyde
• 化学式: C₁₅H₉ClOS
• 分子量: 272.755
• InChiKey: HIRIYMQFSWAGQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴氯苯 、 3-甲醛苯并噻吩 在 palladium diacetate 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以58%的产率得到2-(4'-chlorophenyl)-benzo[b]thiophene-3-carboxaldehyde
  参考文献：
  名称：

  Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus

  摘要：

  The synthesis based on palladium catalytic coupling of 38 new-arylated benzo[b]thiophenes or thiophenes is described in a few steps. We also report the direct arylation of the position 3 of the benzo[b]thiophenic structure, a 'one pot' 2,5-heterodiarylation of thiophenes as well as the synthesis of precursors of amino-acids with a 2-arylated benzo[b]thiophene core. These compounds were evaluated on bacteria strains: most of them did not exhibit any antibiotic activity but were found to selectively inhibit the NorA multidrug transporter of Staphylococcus aureus. As such, they restored the activity of the NorA substrates ciprofloxacin against a resistant S. aureus strain in which this efflux pump is over-expressed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.023

文献信息

• PRODUCTION AND USE OF ZINC AMIDES
  申请人：Knochel Paul

  公开号：US20110288296A1

  公开（公告）日：2011-11-24

  The application relates to a reagent of the general formula R 1 R 2 N—ZnY LiY  (I) wherein R 1 , R 2 are, independently, selected from H, substituted or unsubstituted aryl or heteroaryl containing one or more heteroatoms, linear, branched or cyclic, substituted or unsubstituted alkyl, alkenyl, alkynyl, or silyl derivatives thereof; and R 1 and R 2 together can be part of a cyclic or polymeric structure; and wherein at least one of R 1 and R 2 is other than H; Y is selected from the group consisting of F; Cl; Br; I; CN; SCN; NCO; Halo n , wherein n=3 or 4 and Hal is selected from Cl, Br and I; NO 3 ; BF 4 ; PF 6 ; H; a carboxylate of the general formula R X CO 2 ; an alcoholate of the general formula OR X ; a thiolate of the general formula SR X ; R X P(O)O 2 ; or SCOR X ; or SCSR X ; O n SR x ; wherein n=2 or 3; or NO n , wherein n=2 or 3; and a derivative thereof; wherein R x is a substituted or unsubstituted aryl or heteroaryl containing one or more heteroatoms, linear, branched or cyclic, substituted or unsubstituted alkyl, alkenyl, alkynyl, or derivatives thereof, or H; or as adduct with a solvent; as well as to the preparation and use thereof. 34

  该申请涉及一种通式为R1R2N—ZnY LiY（I）的试剂，其中R1、R2分别选择自H、取代或未取代的含有一个或多个杂原子的芳基或杂环烷基，线性、支链或环状的取代或未取代的烷基、烯基、炔基或其硅基衍生物；R1和R2可以一起构成一个环状或聚合结构；其中至少一个R1和R2不是H；Y选择自F、Cl、Br、I、CN、SCN、NCO、Halon，其中n=3或4，Halon选择自Cl、Br和I；NO3；BF4；PF6；H；通式为RXCO2的羧酸根；通式为ORX的醇根；通式为SRX的硫醇根；RXP（O）O2；或SCORX；或SCSRX；OnSRx；其中n=2或3；或NOn，其中n=2或3；及其衍生物；其中RX是取代或未取代的含有一个或多个杂原子的芳基或杂环烷基，线性、支链或环状的取代或未取代的烷基、烯基、炔基或其衍生物，或H；或作为溶剂的加合物；以及其制备和用途。
• TMPZnCl·LiCl: A New Active Selective Base for the Directed Zincation of Sensitive Aromatics and Heteroaromatics
  作者：Marc Mosrin、Paul Knochel

  DOI：10.1021/ol900342a

  日期：2009.4.16

  polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF via direct zincation using TMPZnCl·LiCl, a new exceptionally mild and efficient base. Activated arenes and heteroarenes are metalated at room temperature. Remarkably, sensitive functions such as an aldehyde as well as a nitro group are tolerated, expanding significantly the scope of directed metalations.

  通过使用新型特温和高效的碱TMPZnCl·LiCl进行直接锌化，可以在THF中有效地制备各种多官能芳基和杂芳基锌试剂。活化的芳烃和杂芳烃在室温下被金属化。显着地，敏感的功能（如醛和硝基）是可以接受的，从而大大扩展了定向金属化的范围。
• Production And Use Of Zinc Amides
  申请人：Ludwig-Maximilians-Universität München

  公开号：US20160215000A1

  公开（公告）日：2016-07-28

  Compounds, methods of making the compounds and methods of using the compounds are generally described herein. The compounds are generally of formula R 1 R 2 N—ZnY LiY, wherein R 1 and R 2 are independently selected from H, aryl, heteroaryl containing one or more heteroatoms, alkyl, alkenyl, alkynyl, and silicon derivatives thereof; and each Y is independently selected from F, Cl, Br, I, CN, SCN, NCO, HalO 3 , HalO 4 , NO 3 , BF 4 , PF 6 , H, an alcoholate of formula OR 5 , a carboxylate of formula R 5 CO 2 ; a thiolate of formula SR 5 , R 5 P(O)O 2 , SCOR 5 , SCSR 5 , O n SR 5 and NO n , wherein n=2 or 3; wherein R 5 is selected from substituted or unsubstituted aryls or heteroaryls containing 3 to 24 carbon atoms and one or more heteroatoms selected from B, O, N, S, Se, P, linear, branched or cyclic, substituted or unsubstituted alkyls, alkenyls, alkynyls or H; and wherein Hal is a halogen selected from Cl, Br and I.

  本文中一般描述了化合物、制备这些化合物的方法以及使用这些化合物的方法。这些化合物通常具有公式R1R2N—ZnY LiY，其中R1和R2独立地选择自H、芳基、含有一个或多个杂原子的杂芳基、烷基、烯基、炔基和它们的硅衍生物；每个Y独立地选择自F、Cl、Br、I、CN、SCN、NCO、HalO3、HalO4、NO3、BF4、PF6、H、公式OR5的醇酸盐、公式R5CO2的羧酸盐、公式SR5的硫醇酸盐、R5P(O)O2、SCOR5、SCSR5、OnSR5和NOn，其中n=2或3；其中R5选择自含有3到24个碳原子和一个或多个来自B、O、N、S、Se、P的杂原子的取代或未取代的芳基或杂芳基，以及取代或未取代的线性、支链或环状的烷基、烯基、炔基或H；而Hal是从Cl、Br和I中选择的卤素。
• Production and use of zinc amides
  申请人：Knochel Paul

  公开号：US09334237B2

  公开（公告）日：2016-05-10

  A reagent of the formula R1R2N—ZnY LiY  (I) wherein R1 and R2 are independently, selected from H, aryl or heteroaryl, linear, branched or cyclic, substituted or unsubstituted alkyl, alkenyl, alkynyl, or silyl derivatives thereof; and R1 and R2 together form part of a cyclic or polymeric structure; R1 and/or R2 is not H; Y is F, Cl, Br, I, CN, SCN, NCO or HalOn, wherein n=3 or 4 and Hal is Cl, Br or I; NO3; BF4; PF6; H; a carboxylate of formula R5CO2; an alcoholate of formula OR5; a thiolate of formula SR5; R5P(O)O2; or SCOR5; or SCSR5; OnSR5; wherein n=2 or 3; or NOn, wherein n=2 or 3; and a derivative thereof; wherein R5 is an aryl or heteroaryl, linear, branched or cyclic, alkyl, alkenyl, alkynyl, or derivatives thereof, or H; or as adduct with a solvent; and preparation and use thereof.

  式为R1R2N—ZnY LiY  (I)的试剂，其中R1和R2独立地选自H、芳基或杂环芳基、线性、支链或环状、取代或未取代的烷基、烯基、炔基或其硅基衍生物；且R1和R2共同形成环状或聚合物结构的一部分；R1和/或R2不是H；Y为F、Cl、Br、I、CN、SCN、NCO或HalOn，其中n=3或4且Hal为Cl、Br或I；NO3；BF4；PF6；H；公式为R5CO2的羧酸盐；公式为OR5的醇盐；公式为SR5的硫醇盐；R5P(O)O2；或SCOR5；或SCSR5；OnSR5；其中n=2或3；或NOn，其中n=2或3，以及其衍生物；其中R5是芳基或杂环芳基、线性、支链或环状、烷基、烯基、炔基或其衍生物，或H；或作为与溶剂的加合物；以及其制备和使用。
• An efficient phosphine-free palladium coupling for the synthesis of new 2-arylbenzo[b]thiophenes
  作者：Jérémie Fournier Dit Chabert、Lionel Joucla、Emilie David、Marc Lemaire

  DOI：10.1016/j.tet.2004.02.011

  日期：2004.3

  Straightforward and rapid access to 2-arylbenzo[b]thiophenes has been developed. It involved a catalytic coupling of 3-activated benzo[b]thiophenes with several aryl halides in the presence of a phosphine-free palladium system. In case of fragile functional groups such as aldehydes, a quaternary ammonium was used as an additive as with the other substrates, the coupling performed better and faster in the presence of a crown ether, the best one being DCH-18-C-6, with good yields and low reaction times. This method would provide a direct access to novel structures of biological interest. (C) 2004 Elsevier Ltd. All rights reserved.