5,5-二甲基-1,3-噻唑烷-2,4-二酮 | 3324-15-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5,5-二甲基-1,3-噻唑烷-2,4-二酮
• 中文别名: 5,5-二甲基四氢-2,4-二酮
• 英文名称: 5,5-dimethylthiazolidine-2,4-dione
• 英文别名: 5,5-dimethyl-thiazolidine-2,4-dione；5,5-Dimethyl-thiazolidin-2,4-dion；5,5-Dimethyl-2,4-thiazolidinedione；5,5-Dimethyl-2,4-diketothiazolidin；5,5-Dimethyl-2,4-dioxo-thiazolidin；5,5-Dimethyl-1,3-thiazolidine-2,4-dione
• CAS: 3324-15-0
• 化学式: C₅H₇NO₂S
• mdl: MFCD20727847
• 分子量: 145.182
• InChiKey: UWXNEBLQDNYFMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 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：

  5,5-二甲基-1,3-噻唑烷-2,4-二酮 在 盐酸 、 sodium tetrahydroborate 、 dimethyl azodicarboxylate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 N-(but-3-enyl)-4-hydroxy-5,5-dimethylthiazolidin-2-one
  参考文献：
  名称：

  噻酰亚胺-烯烃环化

  摘要：

  在氮原子上被不同的π-亲核试剂取代的噻唑烷二酮3-8的区域选择性NaBH 4 / H +还原以良好的产率提供羟基内酰胺9-14。后面的化合物是α-酰化铵离子16的极好的前体，可以在HCOOH中进行立体选择环化，以产生具有不同结构的新型杂环系统。由于闭环中的立体电子控制，很容易实现立体选择性合成，例如8a到24的转换。

  DOI：

  10.1016/0040-4020(82)80103-8
• 作为产物：
  描述：

  methyl 2-methyl-2-thiocyanatopropanoate 在 盐酸 作用下， 生成 5,5-二甲基-1,3-噻唑烷-2,4-二酮
  参考文献：
  名称：

  Wheeler; Barnes, American Chemical Journal, 1900, vol. 24, p. 79

  摘要：

  DOI：

文献信息

• Thia-acyliminium cyclisations
  作者：J.A.M. Hamersma、P.M.M. Nossin、W.N. Speckamp

  DOI：10.1016/s0040-4020(01)96567-6

  日期：1985.1

  by the intermediacy of N-acyliminium species. A similar process applied to lactams 21b–25b affords the pyrrolizidine type compounds 26–35 through consecutive azonium-Cope rearrangement and N-acyliminium ring closure. Additional results are concerned with the use of aromatic rings as π-nucleophiles.

  通过内酰胺类物种的中间作用，羧甲基内酰胺1b–3b的环化可提供高产的大环化合物4–6。应用于内酰胺21b-25b的类似过程可通过连续的偶氮鎓Cope重排和N-嘧啶闭环得到吡咯烷核苷类化合物26-35。其他结果涉及芳环作为π-亲核试剂的使用。
• Studies on antidiabetic agents. III. 5-Arylthiazolidine-2,4-diones as potent aldose reductase inhibitors.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、EIKO IMAMIYA、HIROYUKI TAWADA、KANJI MEGURO、YUTAKA KAWAMATSU、YUJIRO YAMAMOTO

  DOI：10.1248/cpb.30.3601

  日期：——

  Thiazolidine-2, 4-dione derivatives having one or two substituent (s) such as phenyl, heteryl and alkyl group (s) at the 5-position were synthesized and evaluated as aldose reductase inhibitors. Inhibition by the active compounds of the swelling of the lens in a rat-lens-culture assay was also measured. Among these compounds, a series of 5-(3, 4-dialkoxyphenyl) thiazolidine-2, 4-diones showed pronounced activities in both assays. Structure-activity relationships are discussed and a new approach to the synthesis of 5-arylthiazolidine-2, 4-diones is described.

  具有一个或两个取代基（如苯基、杂基和烷基）的噻唑烷-2,4-二酮衍生物在5位合成并评估为醛糖还原酶抑制剂。在鼠晶状体培养检测中，活性化合物的抑制作用也被测量。在这些化合物中，一系列5-(3,4-二烷氧基苯基)噻唑烷-2,4-二酮在两种检测中显示出显著的活性。结构-活性关系进行了讨论，并描述了一种合成5-芳基噻唑烷-2,4-二酮的新方法。
• Dihydroindolone compounds, a process for their preparation and pharmaceutical compositions containing them
  申请人：Ortuno Jean-Claude

  公开号：US20110034460A1

  公开（公告）日：2011-02-10

  Compounds of formula (I): wherein: m and n represent 1 or 2, A represents a pyrrolyl group, X represents a C(O), S(O) or SO 2 group, R 1 and R 2 represent an alkyl group or, together with the nitrogen atom carrying them, form a heterocyclic group, R 3 and R 4 , together with the atoms carrying them, form a heterocyclic group, R 5 represents a hydrogen atom or an alkyl group, R 6 represents a hydrogen atom or a halogen atom. Medicinal products containing the same which are useful in treating cancer.

  式（I）的化合物： 其中： m和n代表1或2， A代表吡咯基， X代表C（O）、S（O）或SO2基团， R1和R2代表烷基或与携带它们的氮原子一起形成杂环基团， R3和R4与携带它们的原子一起形成杂环基团， R5代表氢原子或烷基， R6代表氢原子或卤素原子。 含有这些化合物的药物，可用于治疗癌症。
• NOVEL HALOALKYLSULFONANILIDE DERIVATIVE, HERBICIDE, AND METHOD OF USE THEREOF
  申请人：NIHON NOHYAKU CO., LTD.

  公开号：EP1852425A1

  公开（公告）日：2007-11-07

  A haloalkylsulfonanilide derivative represented by the formula (I): wherein R1 represents haloalkyl; R2 represents H, alkylcarbonyl, optionally substituted phenylcarbonyl, alkoxycarbonyl, optionally substituted phenoxycarbonyl, optionally substituted phenylsulfonyl, etc.; R3 and R4 each represents H, alkyl, cycloalkyl, halogeno, CN, etc.; R5, R6, R7, and R8 each represents H, halogeno, alkyl, cycloalkyl, optionally substituted phenyl (C1-6 alkyl), an optionally substituted heterocycle, etc.; A and W each represents O or S; and X represents one to four substituents selected among H, halogeno, alkyl, alkenyl, optionally substituted phenyl, optionally substituted phenylalkylaminocarbonyl, OH, CN, etc.} and a salt thereof; and a herbicide containing any of these compounds as an active ingredient. The herbicide is excellent in wide applicability, persistency, and selectivity for crops and effectiveness against weeds. It is excellent especially as a herbicide for rice fields.

  公式（I）所表示的一种卤代烷基磺酰苯胺衍生物：其中R1代表卤代烷基；R2代表H、烷基羰基、可选取代的苯基羰基、烷氧羰基、可选取代的苯氧羰基、可选取代的苯基磺酰基等；R3和R4各自代表H、烷基、环烷基、卤素、CN等；R5、R6、R7和R8各自代表H、卤素、烷基、环烷基、可选取代的苯基（C1-6烷基）、可选取代的杂环、等；A和W各自代表O或S；X代表H、卤素、烷基、烯基、可选取代的苯基、可选取代的苯基烷基胺基羰基、OH、CN等中选择的1-4个取代基}及其盐；以及含有这些化合物作为活性成分的除草剂。该除草剂具有广泛适用性、持久性、对作物的选择性和对杂草的有效性。特别是作为稻田除草剂非常出色。
• Novel Haloalkylsulfonanilide Derivative, Herbicide, and Method of Use Thereof
  申请人：Hino Tomokazu

  公开号：US20080274892A1

  公开（公告）日：2008-11-06

  A haloalkylsulfonanilide derivative represented by the formula (I): wherein R 1 represents haloalkyl; R 2 represents H, alkylcarbonyl, optionally substituted phenylcarbonyl, alkoxycarbonyl, optionally substituted phenoxycarbonyl, optionally substituted phenylsulfonyl, etc.; R 3 and R 4 each represents H, alkyl, cycloalkyl, halogeno, CN, etc.; R 5 , R 6 , R 7 , and R 8 each represents H, halogeno, alkyl, cycloalkyl, optionally substituted phenyl(C 1-6 alkyl), an optionally substituted heterocycle, etc.; A and W each represents O or S; and X represents one to four substituents selected among H, halogeno, alkyl, alkenyl, optionally substituted phenyl, optionally substituted phenylalkylaminocarbonyl, OH, CN, etc.} and a salt thereof; and a herbicide containing any of these compounds as an active ingredient. The herbicide is excellent in wide applicability, persistency, and selectivity for crops and effectiveness against weeds. It is excellent especially as a herbicide for rice fields.

  公式（I）所代表的一种卤代烷基磺酰苯胺衍生物：其中R1代表卤代烷基；R2代表H，烷基羰基，可选取代苯基羰基，烷氧羰基，可选取代苯氧羰基，可选取代苯基磺酰基等；R3和R4各自代表H，烷基，环烷基，卤素，CN等；R5，R6，R7和R8各自代表H，卤素，烷基，环烷基，可选取代苯基（C1-6烷基），可选取代杂环等；A和W各自代表O或S；X代表H，卤素，烷基，烯基，可选取代苯基，可选取代苯基烷基氨基羰基，OH，CN等的一到四个取代基}和其盐；以及含有任何这些化合物作为活性成分的除草剂。这种除草剂在广泛适用性、持久性、对作物的选择性和对杂草的有效性方面表现出色。特别是作为稻田除草剂表现出色。