(4S)-4-methyl-1,3-oxazolidine-2-thione | 54013-54-6

• 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: (4S)-4-methyl-1,3-oxazolidine-2-thione
• CAS: 54013-54-6
• 化学式: C₄H₇NOS
• 分子量: 117.172
• InChiKey: QNUJAWVJHFZSNW-VKHMYHEASA-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：

  (4S)-4-methyl-1,3-oxazolidine-2-thione 在 methyloxirane 作用下， 反应 48.0h， 以84%的产率得到(4S)-4-甲基-2-噁唑烷酮
  参考文献：
  名称：

  Desulfurization–Oxygenation of Chiral 1,3-Thiazolidine-2-thiones and 1,3-Oxazolidine-2-thiones Using Propylene Oxide and Microwave Irradiation

  摘要：

  An efficient method for the desulfurization-oxygenation of 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and employing microwave irradiation is described. This strategy of oxygenation of the thiocarbonyl group provides an attractive methodology to prepare chiral 1,3-thiazolidin-2-ones and 1,3-oxazolidin-2-ones from the corresponding precursors in good yields.

  DOI：

  10.1055/s-0032-1317525
• 作为产物：
  描述：

  glucosisymbrin 在 phosphate buffer 、 Nylon 6,6-supported myrosinase 作用下， 生成 (4S)-4-methyl-1,3-oxazolidine-2-thione
  参考文献：
  名称：

  Chemo-enzymatic preparation from renewable resources of enantiopure 1,3-oxazolidine-2-thiones

  摘要：

  Chiral 1,3-oxazolidine-2-thiones were prepared in enantiopure form from renewable resources through an enzymatic process involving immobilized myrosinase (thioglucoside glucohydrolase E.C. 3.2.3.1). (C) 2000 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0957-4166(99)00574-1

文献信息

• Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction
  作者：Wei Tan、Jianpeng Wei、Xuefeng Jiang

  DOI：10.1021/acs.orglett.7b00819

  日期：2017.4.21

  An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were

  已经开发了通过硫和氯仿的组合的有效和实用的硫代羰基替代物。已经建立了多种硫代脲和恶唑烷硫酮，包括具有高选择性的手性硫脲催化剂和手性恶唑烷硫酮助剂。同时，实际上通过克方法通过该方法合成了杀虫剂DiafeNThiuron（一种杀螨剂），ANTU（一种灭鼠剂）和Chloromethiuron（一种杀虫剂）。通过卡宾捕集控制实验进一步确认了作为主要中间体的双氯卡宾。
• Synthesis, X-ray Analysis, and Biological Activities of Novel Oxazolidinethiones
  作者：Nezire Saygılı、Meral Özalp、Leyla Tatar Yıldırım

  DOI：10.1002/jhet.1863

  日期：2014.9

  Oxazolidinethione compounds were synthesized starting from racemic and enantiopure β‐amino alcohols. The molecular structure of oxazolidinethione 6a was elucidated by single‐crystal x‐ray crystallography. Oxazolidinethione compounds screened for antimicrobial activity showed mild minimum inhibitory concentration values.

  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。
• Kjaer; Christensen, Acta Chemica Scandinavica (1947), 1959, vol. 13, p. 1575
  作者：Kjaer、Christensen

  DOI：——

  日期：——