2-(甲硫基)-1,3-噻唑-4(5H)-酮 | 20949-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 2-(甲硫基)-1,3-噻唑-4(5H)-酮
• 中文别名: 2-(甲基硫代)-4(5h)-噻唑酮
• 英文名称: 2-methylsulfanyl-thiazol-4-one
• 英文别名: 2-(methylthio)thiazol-4(5H)-one；2-Methylrhodanin；2-Methylmercapto-Δ²-thiazolon-(4)；2-(Methylsulfanyl)-4,5-dihydro-1,3-thiazol-4-one；2-methylsulfanyl-1,3-thiazol-4-one
• CAS: 20949-66-0
• 化学式: C₄H₅NOS₂
• mdl: MFCD02323098
• 分子量: 147.222
• InChiKey: DYKDFDSOCOSLQI-UHFFFAOYSA-N

物化性质

• 熔点：
  82℃
• 沸点：
  249℃
• 密度：
  1.49
• 闪点：
  105℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  2-(甲硫基)-1,3-噻唑-4(5H)-酮 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 2,4-噻唑烷二酮
  参考文献：
  名称：

  Ginak,A.I. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 1747 - 1749

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl [2-((4-methoxybenzyl)thio)acetyl]carbonodithioimidate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以85%的产率得到2-(甲硫基)-1,3-噻唑-4(5H)-酮
  参考文献：
  名称：

  New Methods for the Synthesis of 2-Aminothiazolones

  摘要：

  [GRAPHICS]Two new methods for the synthesis of 2-aminothiazolones from 2-(4-methoxybenzylthio)acetic acids are described. A single reagent and simple experimental conditions are used in the key tandem deprotection-cyclization process. In the first approach 2-aminothiazolones are directly accessed via cyclization of the corresponding N-acylisothioureas. The second complementary approach provides access to a variety of 2-thiomethylthiazoiones via cyclization of N-acyldithioimidates. The product 2-thiomethylthiazol ones are then efficiently converted to 2-aminothiazolones via amine displacement.

  DOI：

  10.1021/jo702369f

文献信息

• Diversity-Oriented Approach to Spirorhodanines via a [2+2+2] Cyclotrimerization
  作者：Sambasivarao Kotha、Gaddamedi Sreevani

  DOI：10.1002/ejoc.201800775

  日期：2018.11.25

  Mo(CO)6 was used as a catalyst for the synthesis of spirorhodanine derivatives with propargyl halides as co‐partners, via a [2+2+2] cyclotrimerization reaction. Synthesis of spirorhodanines by utilizing o‐xylylene dibromide was also developed.

  Mo（CO）6用作通过[2 + 2 + 2]环三聚反应合成炔丙基卤化物作为伴生气的螺hodanhodanine衍生物的催化剂。还开发了利用邻二甲苯基二溴化物合成螺hodanhodanines。
• Dithiocarbamate as an efficient intermediate for the synthesis of 2-(alkylthio)thiazol-4(5<i>H</i>)-ones
  作者：Azim Ziyaei Halimehjani、M. Ali Alaei、Farzaneh Soleymani Movahed、Negin Jomeh、Mohammad R. Saidi

  DOI：10.1080/17415993.2016.1194421

  日期：2016.9.2

  ABSTRACT An effective approach for the synthesis of 2-(alkylthio)thiazol-4(5H)-ones from alkyl dithiocarbamates and chloroacetyl chloride in the presence of NaHCO3 has been developed. Good to excellent yields of products, simple reaction conditions and general applicability are the most important advantages of this protocol. GRAPHICAL ABSTRACT

  摘要 已开发出一种在 NaHCO3 存在下由二硫代氨基甲酸烷基酯和氯乙酰氯合成 2-(烷硫基)噻唑-4(5H)-酮的有效方法。该协议最重要的优点是产品产量高、反应条件简单、适用性好。图形概要
• AMINOTHIAZOLONES AS ESTROGEN RELATED RECEPTOR-ALPHA MODULATORS
  申请人：Bignan Gilles

  公开号：US20110200587A1

  公开（公告）日：2011-08-18

  The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

  本发明涉及式(I)的化合物，制备这些化合物的方法，组合物，中间体及其衍生物，并用于治疗包括但不限于强直性脊柱炎、动脉粥样硬化、关节炎（如类风湿关节炎、感染性关节炎、儿童关节炎、银屑病性关节炎、反应性关节炎）、与骨相关的疾病（包括与骨形成有关的疾病）、乳腺癌（包括对抗雌激素治疗无效的癌症）、心血管疾病、软骨相关疾病（如软骨损伤/丧失、软骨退化以及与软骨形成有关的疾病）、软骨发育不全、软骨肉瘤、慢性背部损伤、慢性支气管炎、慢性炎症性气道疾病、慢性阻塞性肺病、糖尿病、能量稳态紊乱、痛风、假性痛风、脂质紊乱、代谢综合征、多发性骨髓瘤、肥胖、骨关节炎、遗传性骨发育不全、骨溶解性骨转移、软骨软化症、骨质疏松症、帕金森病、牙周病、多肌痛风、Reiter综合征、重复性应激损伤、高血糖、血糖水平升高和胰岛素抵抗等疾病的方法。
• SUBSTITUTED AMINOTHIAZOLONE INDAZOLES AS ESTROGEN RELATED RECEPTOR-ALPHA MODULATORS
  申请人：BIGNAN Gilles

  公开号：US20110150864A1

  公开（公告）日：2011-06-23

  The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

  该发明涉及式(I)的化合物，制备这些化合物的方法，组合物，中间体及其衍生物，并用于治疗包括但不限于强直性脊柱炎、动脉粥样硬化、关节炎（如类风湿性关节炎、感染性关节炎、儿童关节炎、银屑病性关节炎、反应性关节炎）、与骨相关的疾病（包括与骨形成有关的疾病）、乳腺癌（包括对抗雌激素治疗无效的癌症）、心血管疾病、软骨相关疾病（如软骨损伤/丧失、软骨退化以及与软骨形成有关的疾病）、软骨发育不良、软骨肉瘤、慢性腰部损伤、慢性支气管炎、慢性炎症性气道疾病、慢性阻塞性肺疾病、糖尿病、能量稳态紊乱、痛风、假性痛风、脂质紊乱、代谢综合征、多发性骨髓瘤、肥胖、骨关节炎、遗传性骨发育不全、骨转移性溶骨性转移、软骨软化症、骨质疏松症、帕金森病、牙周病、多肌痛风、Reiter综合征、重复性应激损伤、高血糖、血糖水平升高和胰岛素抵抗等疾病的条件。
• Facile Construction of Structurally Diverse Thiazolidinedione-Derived Compounds via Divergent Stereoselective Cascade Organocatalysis and Their Biological Exploratory Studies
  作者：Yongqiang Zhang、Shengzheng Wang、Shanchao Wu、Shiping Zhu、Guoqiang Dong、Zhenyuan Miao、Jianzhong Yao、Wannian Zhang、Chunquan Sheng、Wei Wang

  DOI：10.1021/co400022r

  日期：2013.6.10

  article, we present a new approach by merging two powerful synthetic tactics, divergent synthesis and cascade organocatalysis, to create a divergent cascade organocatalysis strategy for the facile construction of new "privileged" substructure-based DOS (pDOS) library. As demonstrated, notably 5 distinct molecular architectures are produced facilely from readily available simple synthons thiazolidinedione

  在本文中，我们通过合并两种强大的合成策略（发散性合成和级联有机催化）提出了一种新方法，以创建易于级联的新的基于子结构的基于DOS的DOS（pDOS）库的发散级联有机催化策略。如所证明的，通过强大的策略，可以容易地从简单易得的简单合成子噻唑烷二酮及其类似物和α，β-不饱和醛中以1-3个步骤轻松生成5种不同的分子结构。在相似的反应条件下，由结构紧密的反应物有效形成结构多样的新产品，突出了化学的美。尤其，由各自的噻唑烷二酮和罗丹酮与烯醛的有机催化对映选择性3-组分Michael-Michael-aldol级联反应产生结构上不同的螺-噻唑烷二酮和-若丹宁。然而，在相似的反应条件下，异黄酮碱通过迈克尔环化级联反应导致结构上不同的稠合巯基吡喃类支架。该策略可最大程度地减少耗时且成本高昂的合成工作。此外，这些分子具有与天然支架相似的高结构复杂性和功能，立体化学和骨架多样性。在这些分子的初步生物学研究中，