硫代季酮酸 | 51338-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 硫代季酮酸
• 中文别名: 2,4-四氢噻吩二酮；叔-丁基N-噻唑-5-基氨基甲酸酯；4-羟基-2(5H)-噻吩酮；硫代特窗酸
• 英文名称: thiotetronic acid
• 英文别名: 4-Hydroxy-2(5H)-thiophenone；thiolane-2,4-dione
• CAS: 51338-33-1
• 化学式: C₄H₄O₂S
• 分子量: 116.141
• InChiKey: KJLXVAPBVMFHOL-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  304.1±35.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  硫代季酮酸 以 various solvent(s) 为溶剂， 反应 24.0h， 以76%的产率得到5-methyl-3-oxo-3H-1,2-oxathiole
  参考文献：
  名称：

  Saito, Kimitoshi; Yuki, Hidetaka; Ohyama, Toshiyuki, Canadian Journal of Chemistry, 1981, vol. 59, p. 1717 - 1721

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl ester of 2,4(3H,5H)-dioxo-3-thiophenecarboxylic acid 在 三氟乙酸 作用下， 以92%的产率得到硫代季酮酸
  参考文献：
  名称：

  摘要：

  Acylation of (3H,5H)-tetrahydrothiophene-2,4-dione (thiotetronic acid) with acetyl, propionyl, and valeryl chlorides followed by O-C isomerization in the presence of 4-dimethylaminopyridine or acetone cyanohydrin gave rise to 3-acetyl, 3-propanoyl, and 3-pentanoyl derivatives of thiotetronic acid. The reaction of 3-acylthiotetronic acids with diazomethane afforded enol methyl ethers at the endocyclic keto groups. The subsequent reaction of these enol ethers with allylamine, benzylamine, and p-anisidine occurs along the mechanism of vinylog substitution providing the corresponding endocyclic enamino derivatives.

  DOI：

  10.1023/a:1013464314542

文献信息

• Reaction of Enaminones with Benzyltrimethylammmonium Dichloroiodate.
  作者：Kiezo MATSUO、Shigetoshi ISHIDA、Yoshiro TAKUNO

  DOI：10.1248/cpb.42.1149

  日期：——

  Reaction of enaminones with benzyltrimethylammonium dichloroiodate (BTMA·ICl2) in methylene chloride-methanol in the presence of sodium bicarbonate at room temperature gave iodinated products at the α-position of the carbonyl group in good yields within 1 h.

  在二氯甲烷-甲醇中，在碳酸氢钠存在下，在室温下使烯丙酮与二氯碘酸苄基三甲基铵（BTMA-ICl2）反应，在 1 小时内得到羰基 α 位的碘化产物，收率很高。
• Microwave-assisted Claisen rearrangement on a silica gel support
  作者：Sambasivarao Kotha、Kalyaneswar Mandal、Ashoke Chandra Deb、Shaibal Banerjee

  DOI：10.1016/j.tetlet.2004.11.012

  日期：2004.12

  A fast, efficient and environmentally benign solvent-free procedure has been developed for microwave-assisted Claisen rearrangement on a silica gel support. Various bis-allyl ketones were prepared using this protocol.

  已经开发了一种快速，高效且对环境无害的无溶剂程序，用于在硅胶载体上进行微波辅助的克莱森重排。使用该方案制备了各种双烯丙基酮。
• Tetronic, thiotetronic and tetramic acid derivatives as phospholipase A.sub
  申请人：American Home Products Corporation

  公开号：US05420153A1

  公开（公告）日：1995-05-30

  There are disclosed compounds of the formula: ##STR1## wherein X is NR; R is hydrogen or lower alkyl; R.sup.1 and R.sup.2 are each, independently, hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.20 cycloalkyl, phenylloweralkyl, or substituted phenylloweralkyl substituted by halo, lower alkyl, lower alkoxy, halo lower alkyl, amino, monoloweralkylamino, diloweralkylamino or sulfonamido; A is O, S, NR, or a chemical bond; m is 0-15; n is 0-20; p is 0-15, where m+p.ltoreq.15; and the pharmacologically acceptable salts thereof, which by virtue of their ability to inhibit PLA.sub.2, are of use as antiinflammatory agents and there is also disclosed a method for the treatment of immunoinflammatory conditions, such as allergy, anaphylaxis, asthma and inflammation in mammals, as well as in the modulation of PAF-mediated biological processes, such as embryonic implantation, thus making the compounds useful as antifertility agents.

  公开了下列公式的化合物：##STR1## 其中X是NR；R是氢或低碳基；R.sup.1和R.sup.2各自独立地为氢、C.sub.1-C.sub.10烷基、C.sub.3-C.sub.20环烷基、苯基低碳基或取代苯基低碳基，所述取代基被卤素、低碳基、低碳氧基、卤素低碳基、氨基、单低碳基氨基、双低碳基氨基或磺酰胺基所取代；A为O、S、NR或化学键；m为0-15；n为0-20；p为0-15，其中m+p≤15；以及其药理学上可接受的盐，由于它们能够抑制PLA.sub.2的能力，因此可用作抗炎剂，还公开了一种用于治疗免疫炎症疾病的方法，例如过敏、过敏性反应、哮喘和哺乳动物中的炎症，以及在调节PAF介导的生物过程方面，例如胚胎植入，从而使化合物有用作抗生育剂的作用。
• Benzyl and naphthalenylmethyl thiophenones and cyclopentenones as
  申请人：——

  公开号：US05610197A1

  公开（公告）日：1997-03-11

  This invention relates to benzyl and naphthalenylmethyl thiophenones and cyclopentenones, some of which are novel, which have oral antihyperglycemic activity in diabetic mice, a genetic animal model of non-insulin dependent diabetes mellitus. These compounds are represented by the formula ##STR1## wherein: R.sup.2 and R.sup.3 are independently selected from hydrogen, C.sub.1-6 alkyl, halogen, C.sub.1-6 alkoxy, thio-C.sub.1-6 alkyl, or trifluoromethyl or R.sup.2 together with R.sup.3 forms a benzo ring fused to the phenyl ring and optionally substituted with one or two substituents independently selected from C.sub.1-6 alkyl, halogen, C.sub.1-6 alkoxy, thio-C.sub.1-6 alkyl, or trifluoromethyl; R.sup.1 is selected from hydrogen, C.sub.1-6 alkyl, halogen, C.sub.1-6 alkoxy, thio-C.sub.1-6 alkyl, or trifluoromethyl; and R.sup.4 is selected from the group consisting of: ##STR2## wherein R.sup.5 is H or C.sub.1-6 alkyl or a pharmaceutically acceptable salt thereof.

  本发明涉及苯甲基和萘甲基硫代苯酮和环戊烯酮，其中一些是新颖的，具有口服抗高血糖活性，在非胰岛素依赖型糖尿病小鼠遗传动物模型中。这些化合物由以下式子表示：##STR1##其中：R.sup.2和R.sup.3独立地选自氢、C.sub.1-6烷基、卤素、C.sub.1-6烷氧基、硫代C.sub.1-6烷基或三氟甲基，或R.sup.2与R.sup.3一起形成与苯环融合的苯环，可选地被一个或两个独立选自C.sub.1-6烷基、卤素、C.sub.1-6烷氧基、硫代C.sub.1-6烷基或三氟甲基的取代基取代；R.sup.1选自氢、C.sub.1-6烷基、卤素、C.sub.1-6烷氧基、硫代C.sub.1-6烷基或三氟甲基；R.sup.4选自以下组：##STR2##其中R.sup.5为H或C.sub.1-6烷基，或其药学上可接受的盐。
• Tetronic and thiotetronic acid derivatives as phospholipase A.sub.2
  申请人：American Home Products Corporation

  公开号：US05242945A1

  公开（公告）日：1993-09-07

  There are disclosed compounds of the formula: ##STR1## wherein X is --CH.sub.2 R; R is ##STR2## and further when Y=S, R may also be --(CH.sub.2).sub.e CH.sub.3 ; Y is --O--or --S--; R.sup.1 and R.sup.2 are each, independently, hydrogen or lower alkyl; R.sup.3 is indolyl, furyl, phenyl or phenyl optionally mono- or disubstituted independently by alkyl of 1-7 carbon atoms, --C(CH.sub.3).sub.3, --C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3, --C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3, haloloweralkyl, perfluoroalkyl, lower alkoxy, aryl alkoxy, halo or nitro; R.sup.4 and R.sup.5 are, independently, --COCH.sub.2 R.sup.7, --CO.sub.2 R.sup.7, --CONHR.sup.7, geranyl or CH.sub.2 R.sup.3 ; R.sup.6 is hydrogen or lower alkyl; R.sup.7 is geranyl and any moiety selected from R other than ##STR3## A and B are, independently, --O--, --S-- or --NR.sup.6 --; and a is 0-8; b is 1-10 when Y=S, and 2-10 when Y=O; c is 1-3; d is 0-9; and e is 3-18; which by virtue of their ability to inhibit PLA.sub.2, are of use as antiinflammatory agents and there is also disclosed a method for the treatment of immunoinflammatory conditions, such as allergy, anaphylaxis, asthma and inflammation in mammals.

  公开了公式为：##STR1##的化合物，其中X为--CH.sub.2 R; R为##STR2##，当Y=S时，R也可以为--(CH.sub.2).sub.e CH.sub.3 ; Y为--O--或--S--; R.sup.1和R.sup.2各自独立地为氢或低碳基; R.sup.3为吲哚基、呋喃基、苯基或苯基，可独立地被1-7碳原子的烷基、--C(CH.sub.3).sub.3、--C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3、--C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3、卤代低碳基、全氟烷基、低碳基氧、芳基氧、卤基或硝基取代; R.sup.4和R.sup.5独立地为--COCH.sub.2 R.sup.7、--CO.sub.2 R.sup.7、--CONHR.sup.7、香叶醇或CH.sub.2 R.sup.3 ; R.sup.6为氢或低碳基; R.sup.7为香叶醇和除##STR3##以外的任何基团; A和B独立地为--O--、--S--或--NR.sup.6 --; a为0-8; 当Y=S时，b为1-10，当Y=O时，b为2-10; c为1-3; d为0-9; e为3-18; 由于它们具有抑制PLA.sub.2的能力，因此可用作抗炎药物，还公开了一种治疗免疫炎症状况，例如过敏、过敏反应、哮喘和哺乳动物炎症的方法。