5-(4-methylphenyl)tetrahydrothiophen-3-one

• 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: 5-(4-methylphenyl)tetrahydrothiophen-3-one
• 英文别名: 5-(4-Methylphenyl)thiolan-3-one
• 化学式: C₁₁H₁₂OS
• 分子量: 192.282
• InChiKey: HCGHATLMNFTMEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-methylphenyl)tetrahydrothiophen-3-one 在 sodium hydroxide 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 3-(4-methylbenzyl)-1,10-bis(4-methylphenyl)-4H,10H-thieno[3,4-c][1,5]benzothiazepine
  参考文献：
  名称：

  A facile tandem protocol for the regioselective synthesis of novel thienobenzothiazepines

  摘要：

  A series of new 3-benzyl-1,10-diaryl-4H,10H-thieno[3,4-c][1,5]benzothiazepines has been synthesised regioselectively from the reaction of 5-aryl-2,4-bis(arylmethylidene)dihydro-3-thiophenones with o-aminothiophenol in the presence of acetic acid. This transformation presumably occurs via a tandem Michael addition-condensation-isomerisation sequence. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.168
• 作为产物：
  描述：

  在 sodium acetate 、 乙酸酐 作用下， 反应 3.0h， 生成 5-(4-methylphenyl)tetrahydrothiophen-3-one
  参考文献：
  名称：

  新型的2-芳基-3,4-二氢-2 H-噻吩并[3,2- b ]吲哚的微波辅助易位菲舍尔吲哚合成及其抗结核性评价

  摘要：

  从5-芳基二氢-3（2 H）-噻吩与芳基肼的反应中，高选择性地合成了一系列新颖的2-芳基-3,4-二氢-2 H-噻吩并[3,2- b ]吲哚。盐酸盐。发现该反应由微波辅助。评价了噻吩并[3,2- b ]吲哚对结核分枝杆菌H37Rv（MTB）和耐多药结核分枝杆菌（MDR-TB）的体外活性。在筛选出的22种化合物中，发现[2-（2,4-二氯苯基）-7-氟-3,4-二氢-2 H-硫代[3,2- b ]吲哚]（6t）是活性最高的化合物。相对于MTB和MDR-TB的MIC为0.4μg/ mL。

  DOI：

  10.1016/j.bmcl.2009.04.029
• 作为试剂：
  描述：

  ethyl 2-[2-(4-chlorophenyl)-2-oxoethyl]sulfonylacetate 在 5-(4-methylphenyl)tetrahydrothiophen-3-one 、 甲醇 、 对甲基苯甲醛 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以56%的产率得到1-(4-氯苯基)-2-(甲基磺酰基)乙酮
  参考文献：
  名称：

  l-脯氨酸催化的三组分多米诺[3 + 2 + 1]环用于高取代度的含有三个或四个立体中心的噻吩并吡喃的区域和非对映选择性合成

  摘要：

  1-脯氨酸催化的3-[（2-氧代-2-芳基乙基）磺酰基]乙酸乙酯或2-[（（2-乙氧基-2-氧代乙基）磺酰基]乙酸乙酯，芳族醛和5-的三组分反应芳基四氢-3-噻吩酮提供了各种高度取代的噻吩并[3,2- c ]噻喃衍生物。此容易转化推测通过的烯胺形成/醇醛缩合/迈克尔加成/ 6-一锅多米诺顺序发生外切- TRIG环化/消除，并涉及在三C-C键的单次操作的创建和三个新的代在所有情况下都具有完全非对映选择性的立体中心，并且在第一个中约有四分之一。从5-取代的四氢-3-噻吩酮衍生物开始时，非对映异构体比例为7：3。

  DOI：

  10.1021/jo9021327

文献信息

• A facile domino protocol for the regioselective synthesis and discovery of novel 2-amino-5-arylthieno-[2,3-b]thiophenes as antimycobacterial agents
  作者：Kamaraj Balamurugan、Subbu Perumal、Aaramadaka Sunil Kumar Reddy、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.tetlet.2009.08.085

  日期：2009.11

  2-amino-5-arylthieno[2,3-b]thiophenes has been synthesized regioselectively from the reaction of 5-aryldihydro-3(2H)-thiophenones with ethyl cyanoacetate/malononitrile and sulfur powder in the presence of morpholine under thermal as well as microwave irradiation conditions. This transformation presumably occurs via domino Gewald reaction–dehydrogenation sequence. The 2-amino-5-arylthieno[2,3-b]thiophenes were

  在2-甲基苯甲酸酯存在下，由5-芳基二氢-3（2 H）-噻吩酮与氰基乙酸乙酯/丙二腈和硫粉的反应区域选择性合成了一系列新型的2-氨基-5-芳基噻吩并[2,3- b ]噻吩。热和微波照射条件下的吗啉。这种转变大概是通过多米诺骨牌Gewald反应-脱氢序列发生的。评价了2-氨基-5-芳基噻吩并[2,3- b ]噻吩在体外对结核分枝杆菌H37Rv（MTB）和耐多药结核分枝杆菌（MDR-TB）的活性。在筛选出的12种化合物中，乙基2-氨基-5-（1-萘基）噻吩并[2,3- b发现噻吩-3-羧酸盐是最具活性的化合物，其针对MTB和MDR-TB的MIC为1.1μM。
• A novel three-component tandem protocol for the regioselective synthesis of 1-(2-arylmethyl-5-aryl-3-thienyl)pyrrolidines and piperidines
  作者：Subramanian Vedhanarayanan Karthikeyan、Subbu Perumal、K.K. Balasubramanian

  DOI：10.1016/j.tetlet.2007.06.142

  日期：2007.8

  A series of new substituted 1-(2-arylmethyl-5-aryl-3-thienyl)pyrrolidines and piperidines were synthesised by one-pot, three-component tandem reactions of 5-aryldihydro-3(2H)-thiophenone, aromatic aldehydes and pyrrolidine/piperidine under solvent-free microwave irradiation. This facile transformation occurs presumably via a tandem enamine formation–carbonyl addition–dehydration–isomerisation sequence

  通过5-芳基二氢-3（2H）-噻吩，芳族醛的一锅三组分串联反应合成了一系列新的取代的1-（2-芳基甲基-5-芳基-3-噻吩基）吡咯烷和哌啶无溶剂微波辐射下的吡咯烷/哌啶和吡咯烷/哌啶。这种容易的转变大概是通过串联烯胺形成-羰基加成-脱水-异构化序列而发生的。
• A one-pot domino synthesis and discovery of highly functionalized dihydrobenzo[b]thiophenes as AChE inhibitors
  作者：Veerappan Jeyachandran、Raju Ranjith Kumar、Mohamed Ashraf Ali、Tan Soo Choon

  DOI：10.1016/j.bmcl.2013.01.122

  日期：2013.4

  A library of novel 5-amino-2,7-diaryl-2,3-dihydrobenzo[b]thiophene-4,6-dicarbonitriles have been synthesized regioselectively in good yields through the one-pot domino reactions of 5-aryldihydro-3(2H)-thiophenones, malononitrile and aromatic aldehydes in the presence of morpholine. This transformation presumably involves Knoevenagel condensation-Michael addition-intramolecular Thorpe-Ziegler cyclization-Tautomerization-Elimination sequence of reactions. These compounds were evaluated for their acetylcholinesterase (AChE) inhibitory activity and 5-amino-2,7-bis(4-methoxyphenyl)-2,3-dihydrobenzo[b]thiophene-4,6-dicarbonitrile was found to be the most potent against AChE with IC50 4.16 mu mol/L. (C) 2013 Elsevier Ltd. All rights reserved.
• A microwave-assisted, facile, regioselective Friedländer synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2- b ]quinolines
  作者：Kamaraj Balamurugan、Veerappan Jeyachandran、Subbu Perumal、Thimmappa H. Manjashetty、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2009.11.011

  日期：2010.2

  A series of 2,9-diaryl-2,3-dihydrothieno[3,2-b]quinolines have been synthesized regioselectively by Friedlander annulation of 5-aryldihydro-3(2H)-thiophenones and 2-aminobenzophenones in the presence of trifluoroacetic acid in good yields under microwave irradiation at 100 degrees C. The 2,9-diatyl-2,3-dihydrothieno[3,2-b]quinolines were screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among the 17 compounds screened, 7-chloro-2-(2,4-dichlorophenyl)-9-phenyl-2,3-dihydrothieno-[3,2-b]quinoline and 7-chloro-2-(3-nitrophenyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline display maximum activity with MIC of 0.90 and 0.95 mu M against MTB and MDR-TB respectively. (C) 2009 Elsevier Masson SAS. Ail rights reserved.
• <scp>l</scp>-Proline-Catalyzed Three-Component Domino [3+2+1] Annulation for the Regio- and Diastereoselective Synthesis of Highly Substituted Thienothiopyrans Containing Three or Four Stereocenters
  作者：Sethuraman Indumathi、Subbu Perumal、J. Carlos Menéndez

  DOI：10.1021/jo9021327

  日期：2010.1.15

  2-[(2-oxo-2-arylethyl)sulfonyl]acetate or ethyl 2-[(2-ethoxy-2-oxoethyl)sulfonyl]acetate, aromatic aldehydes, and 5-aryltetrahydro-3-thiophenone furnished a variety of highly substituted thieno[3,2-c]thiopyran derivatives. This facile transformation presumably occurs via a one-pot domino sequence of enamine formation/aldol condensation/Michael addition/6-exo-trig cyclization/elimination and involves the

  1-脯氨酸催化的3-[（2-氧代-2-芳基乙基）磺酰基]乙酸乙酯或2-[（（2-乙氧基-2-氧代乙基）磺酰基]乙酸乙酯，芳族醛和5-的三组分反应芳基四氢-3-噻吩酮提供了各种高度取代的噻吩并[3,2- c ]噻喃衍生物。此容易转化推测通过的烯胺形成/醇醛缩合/迈克尔加成/ 6-一锅多米诺顺序发生外切- TRIG环化/消除，并涉及在三C-C键的单次操作的创建和三个新的代在所有情况下都具有完全非对映选择性的立体中心，并且在第一个中约有四分之一。从5-取代的四氢-3-噻吩酮衍生物开始时，非对映异构体比例为7：3。