4,5-dihydro-5-phenyl-3(2H)-thiophenone | 36748-19-3

• 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: 4,5-dihydro-5-phenyl-3(2H)-thiophenone
• 英文别名: 2-phenyl-4-oxotetrahydrothiophene；5-phenyltetrahydro-3-thiophenone；5-phenylthiolan-3-one；5-phenyl-dihydro-thiophen-3-one；5-Phenyl-dihydro-thiophen-3-on；2-phenyl-4-oxo-tetrahydrothiophene
• CAS: 36748-19-3
• 化学式: C₁₀H₁₀OS
• 分子量: 178.255
• InChiKey: MUPAYYMHEJKLQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  311.5±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  4,5-dihydro-5-phenyl-3(2H)-thiophenone 在 盐酸羟胺 、 barium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到4,5-dihydro-5-phenyl-3(2H)-thiophenone oxime
  参考文献：
  名称：

  Solvent effects in thermal (2 + 2) cycloaddition reactions. Intramolecular capture of 1,4-dipolar intermediates vs. (2 + 2) cycloaddition in reactions of 3-(1-pyrrolidinyl)thiophenes with electron-deficient acetylenes

  摘要：

  DOI：

  10.1021/jo00315a038
• 作为产物：
  描述：

  反式-肉桂酸乙酯 在 硫酸 、 sodium 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 6.33h， 生成 4,5-dihydro-5-phenyl-3(2H)-thiophenone
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

  摘要：

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.009

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。
• <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。
• A microwave-assisted facile regioselective Fischer indole synthesis and antitubercular evaluation of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles
  作者：Subramanian Vedhanarayanan Karthikeyan、Subbu Perumal、Krithika Arun Shetty、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2009.04.029

  日期：2009.6

  A series of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles has been synthesised regioselectively in good yields from the reaction of 5-aryldihydro-3(2H)-thiophenones and arylhydrazine hydrochloride. This reaction is found to be assisted by microwaves. The thieno[3,2-b]indoles were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis

  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。
• Substituted pyridines/pyrimidines, their preparation, and their use as pesticides
  申请人：Hoechst Schering

  公开号：US06207668B1

  公开（公告）日：2001-03-27

  The present invention relates to novel substituted pyridines/pyrimidines of the formula I where A is CH or N; X is NH, oxygen or S(O)q where q is 0, 1 or 2; Y is a direct bond or CH2; Z is oxygen, NR7 or S(O)m is 0, 1 or 2, and the radicals R1, R2, R3, R4, R5, R6 and R7 are as defined in the description, to processes for their preparation, and to their use as pesticides, fungicides, ovicides or as veterinary medicaments.

  本发明涉及公式I的新型取代吡啶/嘧啶，其中A为CH或N；X为NH、氧或S(O)q，其中q为0、1或2；Y为直接键或CH2；Z为氧、NR7或S(O)m，其中m为0、1或2，以及基团R1、R2、R3、R4、R5、R6和R7如描述中所定义的，其制备方法以及它们作为杀虫剂、杀菌剂、卵杀剂或兽医药物的用途。
• Furo-, Pyrano- und Oxepino-chinoline sowie deren Schwefel-Analoga
  作者：G. Kempter、P. Zänker、H.-D. Zürner

  DOI：10.1002/ardp.19673001005

  日期：——

  Aus aromatischen o‐Amino‐ketonen und heterocyclischen Ringketonen, die in 3‐ bzw. 4‐Stellung zur Carbonylgruppe Sauerstoff bzw. Schwefel enthalten, werden heterocyclisch b‐kondensierte Chinoline hergestellt.

  由芳香族邻氨基酮和杂环酮（其 3 位或 4 位含有氧和硫）到羰基，生成杂环 b-稠合喹啉。