5-(1-methylethylidene)-2-thioxo-1,3-thiazolidin-4-one | 28989-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-(1-methylethylidene)-2-thioxo-1,3-thiazolidin-4-one
• 英文别名: 5-isopropylidenerhodanine；5-isopropylidene-2-thioxo-thiazolidin-4-one；5-Isopropyliden-2-thioxo-thiazolidin-4-on；5-(1-methylethylidene)-2-thioxo-4-thiazolidinone；5-Isopropyliden-rhodanin；5-Isopropylidenrhodanin；4-Thiazolidinone, 5-(1-methylethylidene)-2-thioxo-；5-propan-2-ylidene-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 28989-47-1
• 化学式: C₆H₇NOS₂
• mdl: MFCD07793857
• 分子量: 173.26
• InChiKey: MZEPNNPNBSNIER-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(1-methylethylidene)-2-thioxo-1,3-thiazolidin-4-one 在 sodium hydroxide 作用下， 生成 α-thioxo-isovaleric acid
  参考文献：
  名称：

  Maimind; Berlin, Zhurnal Obshchei Khimii, 1950, vol. 20, p. 1626; engl. Ausg. S. 1687

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Amino-5-isopropyliden-2-thioxo-thiazolidin-4-on 在 sodium nitrite 作用下， 生成 5-(1-methylethylidene)-2-thioxo-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Sandstroem, Arkiv foer Kemi, 1956, vol. 8, p. 487,502

  摘要：

  DOI：

文献信息

• SYNTHESE DES ACIDES AMINES A PARTIR DE LA RHODANINE
  作者：Roger Gaudry、Robert A. Mcivor

  DOI：10.1139/v51-051

  日期：1951.6.1

  The Gränacher method has been investigated to discover its applicability to the synthesis of a variety of natural amino acids. The procedure has been simplified for phenylalanine and tyrosine, and extended to valine and isoleucine. An unusual product of the oximation of α-thioketo-β-(p-methoxyphenyl)propionic acid is described.

  Gränacher方法已被研究，以发现其在合成各种天然氨基酸中的适用性。该程序已经简化用于苯丙氨酸和酪氨酸，并扩展到缬氨酸和异亮氨酸。描述了α-硫代酮基-β-(对甲氧基苯基)丙酸的羟肟化反应的异常产物。
• Preparation of vic-Mercaptoisopentanols
  作者：Daniel Végh、Michal Uher、Oľga Rajniaková、Miloslava Dandárová、Milan Kováč

  DOI：10.1135/cccc19930404

  日期：——

  This paper describes the preparation of some mercaptoisopentanols: 2-mercapto-3-methyl-1-butanol (I), 1-mercapto-3-methyl-2-butanol (II), 3-mercapto-3-methyl-2-butanol (III) and the unsaturated analogue of compound I - 2-mercapto-3-methyl-2-buten-1-ol (IV). These compounds belong to the flavonoid group present in food responsible for deterioration of their gustatory properties.

  这篇论文描述了一些巯基异戊醇的制备过程：2-巯基-3-甲基-1-丁醇（I）、1-巯基-3-甲基-2-丁醇（II）、3-巯基-3-甲基-2-丁醇（III）以及化合物I的不饱和类似物-2-巯基-3-甲基-2-丁烯-1-醇（IV）。这些化合物属于食物中存在的类黄酮类化合物，会导致食物味道恶化。
• [EN] SPIRO-THIAZOLONES<br/>[FR] SPIRO-THIAZOLONES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2016075181A1

  公开（公告）日：2016-05-19

  The present invention provides spiro-thiazolones, which act as V1a receptor modulators, and in particular as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments. The present compounds are useful as therapeutics acting peripherally and centrally in the conditions of inappropriate secretion of vasopressin, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, aggressive behavior and phase shift sleep disorders, in particular jetlag.

  本发明提供了作为V1a受体调节剂的螺环噻唑酮，特别是作为V1a受体拮抗剂，它们的制备方法，含有它们的药物组合物以及它们作为药物的用途。本化合物在周围和中枢作用下，对于不当分泌加压素、焦虑、抑郁症、强迫症、自闭症谱系障碍、精神分裂症、攻击性行为和相位错位睡眠障碍，特别是时差反应等症状具有治疗作用。
• 4-[3-Dimethylamino-1-(2-dimethylaminovinyl]prop-2-enylidene]-2-phenyl-1,3-oxazol-5(4H)-one and 5-[3-Dimethylamino-1-(2-dimethylaminovinyl)prop-2-enylidene]-3-methyl-2-thioxo-1,3-thiazolidin-4-one in the Synthesis of 1,4-Dihydropyridine Derivatives
  作者：Branko Stanovnik、Ales Hvala、Lucija Jukic Sorsak、Gorazd Sorsak、Urska Bratusek、Jurij Svete、Nina Lah、Ivan Leban

  DOI：10.3987/com-02-9433

  日期：——

  afforded 1,4-dihydropyridine derivatives (5) and (16) in 19-94% yields. Reactions of oxazolones (5) with hydrazine hydrate gave the corresponding imidazolones (6), while upon base- or acid-catalysed methanolysis of 5 methyl (benzoylamino)(1-substituted pyridin-4(1H)-ylidene)acetates (7) were obtained. Catalytic hydrogenation of 7a furnished α-(piperidin-4-yl)glycine derivative (8) and/or α-(pyridin-2-yl)glycine

  4-3-二甲氨基-1-[2-(二甲氨基)乙烯基]丙-2-亚乙烯基]-2-苯基-1,3-恶唑-5(4H)-一(3)和5-3-二甲氨基-1-[2-(二甲基氨基)乙烯基]prop-2-enylidene]-3-methyl-2-thioxo-1,3-thiazolidin-4-one (15) 由 4-(1-methylethyleneidene) 制备-2-phenyl-1,3-oxazol-5(4H)-one (2) 和 5-(1-methylethyleneidene)-2-thioxo-1,3-thiazolidin-4-one (11)。用伯胺处理化合物(3)和(15)得到19-94％产率的1，4-二氢吡啶衍生物(5)和(16)。恶唑酮 (5) 与水合肼反应得到相应的咪唑酮 (6)，而在碱或酸催化的 5 甲基 (苯甲酰氨基)(1-取代的吡啶-4(1H)-亚甲基)乙酸酯 (7) 的甲醇分解下，获得。7a
• Brønsted acid-catalyzed aza-Mannich reaction of N-Boc aminals: access to multifunctional rhodanine/hydantoin derivatives
  作者：Kaihe Zou、Xin-Yan Wu、Jinxing Ye

  DOI：10.1007/s11164-017-2892-9

  日期：2017.8

  An effective aza-Mannich reaction between olefinic rhodanines/hydantoins and N-Boc aminals catalyzed by Brønsted acid has been developed. Multifunctional rhodanine/hydantoin derivatives were obtained in 71–86% yields and an up to 95/5 Z/E ratio under mild conditions.

  已经开发了由布朗斯台德酸催化的 烯烃若丹宁/乙内酰脲与N- Boc缩醛之间的有效氮杂-曼尼希反应。在温和条件下，以71-86％的产率获得了多功能的若丹宁/乙内酰脲衍生物，其收率高达95/5 Z / E。

表征谱图