4-甲基-1,3-恶唑烷-2-硫酮 | 54013-54-6

• 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: 4-甲基-1,3-恶唑烷-2-硫酮
• 英文名称: 4-methyl-1,3-oxazolidine-2-thione
• 英文别名: 4-methyl-2-oxazolidinethione；4-methyl-oxazolidine-2-thione；(+/-)-4-methyl-oxazolidine-2-thione；(+/-)-4-Methyl-oxazolidin-2-thion；4-Methyloxazolidin-2-thion
• CAS: 54013-54-6
• 化学式: C₄H₇NOS
• mdl: MFCD19217275
• 分子量: 117.172
• InChiKey: QNUJAWVJHFZSNW-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C(Solv: water (7732-18-5))
• 沸点：
  132.7±23.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲基-1,3-恶唑烷-2-硫酮 在 五氯化磷 、 三氯氧磷 作用下， 生成 2-chloro-4,5-dihydro-4-methyloxazole
  参考文献：
  名称：

  Thiophene-Anthranilamides as Highly Potent and Orally Available Factor Xa Inhibitors

  摘要：

  There remains a high unmet medical need for a safe oral therapy for thrombotic disorders. The serine protease factor Xa (fXa), with its central role in the coagulation cascade, is among the more promising targets for anticoagulant therapy and has been the subject of intensive drug discovery efforts. Investigation of a hit from high-throughput screening identified a series of thiophene-substituted anthranilamides as potent nonamidine fXa inhibitors. Lead optimization by incorporation of hydrophilic groups led to the discovery of compounds with picomolar inhibitory potency and micromolar in vitro anticoagulant activity. Based on their high potency, selectivity, oral pharmacokinetics, and efficacy in a rat venous stasis model of thrombosis, compounds ZK 814048 (10b), ZK 810388 (13a), and ZK 813039 (17m) were advanced into development.

  DOI：

  10.1021/jm070125f
• 作为产物：
  描述：

  DL-氨基丙醇 、 硫光气 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以27%的产率得到4-甲基-1,3-恶唑烷-2-硫酮
  参考文献：
  名称：

  新型恶唑烷硫酮的合成，X射线分析和生物活性

  摘要：

  恶唑烷硫酮化合物是由外消旋和对映体纯的β-氨基醇合成的。通过单晶X射线晶体学阐明了恶唑烷硫酮6a的分子结构。筛选出的具有抗菌活性的恶唑烷硫酮化合物显示出适度的最小抑菌浓度值。

  DOI：

  10.1002/jhet.1863

文献信息

• Selective S-arylation of 2-oxazolidinethiones and selective N-arylation of 2-benzoxazolinones/2-benzimidazolinones
  作者：Chu-Han Sun、Yi Lu、Qing Zhang、Rong Lu、Lin-Qing Bao、Mei-Hua Shen、Hua-Dong Xu

  DOI：10.1039/c7ob00040e

  日期：——

  There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes

  环状2-恶唑烷硫酮和2-苯并恶唑烷硫酮与芳烃的反应存在三种可能的模式，即（a）S-芳基化，（b）N-芳基化，和（c）芳基插入硫代羰基（CS ）中。我们的研究表明，小号-arylation胜出，得到小号芳dihydrooxazoles。相反，对于相关的反应的环状2-苯并恶唑啉酮和2-苯并咪唑啉酮与arynes，发现Ñ -arylation outcompetes ö -arylation和芳炔插入到C O基团，得到ñ -芳基2-benzoxazolinones和Ñ -芳基2 -苯并咪唑啉酮。
• Synthese einiger Thiooxazolidone
  作者：M. Viscontini、K. Adank

  DOI：10.1002/hlca.19500330735

  日期：——

  Es werden die Synthesen von d, l-4-Methyl-, d, l-4-Benzyl- und d, l-p-Oxybenzyl-thiooxazolidon aus den entsprechenden Aminoalkoholen beschrieben.

  的合成d，升-4-甲基，d，升-4-苄和d，升从相应的氨基醇-对-氧苄-thiooxazolidone中描述。
• 一种2-苯硫基-4,5-二氢噁唑的合成方法
  申请人：常州大学

  公开号：CN106986841A

  公开（公告）日：2017-07-28

  本发明涉及一种2‑苯硫基‑4,5‑二氢噁唑的合成方法，以2‑噁唑烷硫酮、苯炔前体和氟化铯为原料，加热反应，通过一步法即可制得2‑苯硫基‑4,5‑二氢噁唑，反应原料易得，操作简便，条件温和，产率较高。
• Kjaer; Christensen, Acta Chemica Scandinavica (1947), 1959, vol. 13, p. 1575
  作者：Kjaer、Christensen

  DOI：——

  日期：——
• Thiophene-Anthranilamides as Highly Potent and Orally Available Factor Xa Inhibitors
  作者：Bin Ye、Damian O. Arnaiz、Yuo-Ling Chou、Brian D. Griedel、Rushad Karanjawala、Wheeseong Lee、Michael M. Morrissey、Karna L. Sacchi、Steven T. Sakata、Kenneth J. Shaw、Shung C. Wu、Zuchun Zhao、Marc Adler、Sarah Cheeseman、William P. Dole、Janice Ewing、Richard Fitch、Dao Lentz、Amy Liang、David Light、John Morser、Joseph Post、Galina Rumennik、Babu Subramanyam、Mark E. Sullivan、Ron Vergona、Janette Walters、Yi-Xin Wang、Kathy A. White、Marc Whitlow、Monica J. Kochanny

  DOI：10.1021/jm070125f

  日期：2007.6.1

  There remains a high unmet medical need for a safe oral therapy for thrombotic disorders. The serine protease factor Xa (fXa), with its central role in the coagulation cascade, is among the more promising targets for anticoagulant therapy and has been the subject of intensive drug discovery efforts. Investigation of a hit from high-throughput screening identified a series of thiophene-substituted anthranilamides as potent nonamidine fXa inhibitors. Lead optimization by incorporation of hydrophilic groups led to the discovery of compounds with picomolar inhibitory potency and micromolar in vitro anticoagulant activity. Based on their high potency, selectivity, oral pharmacokinetics, and efficacy in a rat venous stasis model of thrombosis, compounds ZK 814048 (10b), ZK 810388 (13a), and ZK 813039 (17m) were advanced into development.