pyran-2-thione | 23639-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: pyran-2-thione
• 英文别名: Pyran-2-thion；2H-pyran-2-thione
• CAS: 23639-33-0
• 化学式: C₅H₄OS
• 分子量: 112.152
• InChiKey: SCXKWEIRWVHPIN-UHFFFAOYSA-N

物化性质

• 熔点：
  49 °C
• 沸点：
  158.9±23.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pyran-2-thione 、 亚硝基苯 生成 3-phenyl-2,8-dioxa-3-azabicyclo[4.2.0]oct-4-ene-7-thione
  参考文献：
  名称：

  AUGELMANN, G.;FRITZ, H.;RIHS, G.;STREITH, J., J. CHEM. SOC. CHEM. COMMUN., 1982, N 19, 1112-1113

  摘要：

  DOI：
• 作为产物：
  描述：

  2H-吡喃-2-酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以27%的产率得到pyran-2-thione
  参考文献：
  名称：

  5- and 6-Membered (thio)lactones are prodrug type carbonic anhydrase inhibitors

  摘要：

  The inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1) with (thio) coumarins has been recently reported (Maresca et al., J. Am. Chem. Soc. 2009, 131, 3057). Here we demonstrate that a series of gamma- and delta-(thio) lactones also act as mechanism based, prodrug type CA inhibitors, similar to the (thio) coumarins. Through the esterase activity of CA, these compounds are hydrolyzed in situ to the corresponding hydroxy/keto/mercapto acids which thereafter act as inhibitors. CA isoforms I and IX were efficiently inhibited by simple such compounds, with KIs in the range of 0.92-19.1 mu M, whereas CA II was not inhibited at all. Isoform-selective CA inhibitors which spare the ubiquitous off-target CA II may have interesting applications for example for selectively inhibiting the tumor-associated CA IX, a validated anticancer target. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.018

文献信息

• Cycloaddition of 2H-Pyran-2-thiones with Nitroso Derivatives. An Unexpected Cycloaddition-Rearrangement Reaction
  作者：Albert Defoin、G�rard Augelmann、Hans Fritz、Guillaume Geffroy、Christian Schmidlin、Jacques Streith

  DOI：10.1002/hlca.19850680724

  日期：1985.11.13

  Reaction of pyran-2-thiones 4 with nitroso derivatives led surprisingly to type-8 (19) adducts which proved to be isomeric with the initially expected primary Diels-Alder cycloadducts 5. Methyl 2-thioxo-2H-pyran-5-carboxylate (4f), when reacted with nitrosobenzene at -10°, led quantitatively to the thieto-oxazine intermediate 13, which turned out to be the cornerstone of the complex cycloaddition-rearrangement

  吡喃-2-硫酮的反应4与导致令人惊奇的亚硝基衍生物型- 8（19被证明是同分异构体与最初的预期主要）加合物狄尔斯-阿尔德cycloadducts 5。当在-10°下与亚硝基苯反应时，2-thioxo-2 H -pyran-5-羧酸甲酯（4f）定量地导致硫代恶嗪中间体13转化为复杂的环加成重排5 的基石。8个反应途径（方案3）。差示扫描量热法，与18a 19a相同转化，被允许证明该多步重排总体上是高温放热过程，最终产物19代表沿着该反应路径的能量吸收器。
• An unexpected addition product of nitrosobenzene with pyran-2-thione
  作者：G�rard Augelmann、Hans Fritz、Grety Rihs、Jacques Streith

  DOI：10.1039/c39820001112

  日期：——

  Pyran-2-thione reacts with stocheiometric amounts of nitrosobenzene, leading on quantitative yield to an unusual adduct whose structures is unambiguously determined by n.m.r. spectroscopy and X-ray data.

  吡喃-2-硫酮与化学计量的亚硝基苯反应，导致定量收率生成不寻常的加合物，其加合物的结构由核磁共振谱和X射线数据明确确定。
• DEFOIN, A.;AUGEIMANN, G.;FRITZ, H.;GEFFROY, G.;SCHMIDLIN, C.;STREITH, J., HELV. CHIM. ACTA, 1985, 68, N 7, 1998-2014
  作者：DEFOIN, A.、AUGEIMANN, G.、FRITZ, H.、GEFFROY, G.、SCHMIDLIN, C.、STREITH, J.

  DOI：——

  日期：——
• SHUSHERINA N. P.; PILIPENKO V. S., ZH. ORGAN. XIMII, 1978, 14, HO 4, 895
  作者：SHUSHERINA N. P.、 PILIPENKO V. S.

  DOI：——

  日期：——
• Controllable Cycloadditions between 2<i>H</i>-(Thio)pyran-2-(thi)ones and Strained Alkynes: A Click-and-Release Strategy for COS/H₂S Generation
  作者：Qi Cui、Tony W. Pan、Meg Shieh、Shane S. Kelly、Shi Xu、Wei-Jun Qian、Ming Xian

  DOI：10.1021/acs.orglett.2c02819

  日期：2022.10.14

表征谱图