methacryloyl isothiocyanate | 56368-95-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 英文名称: methacryloyl isothiocyanate
• 英文别名: Methacryloylisothiocyanat；2-methyl-acryloyl isothiocyanate；Methacryloyl-isothiocyanat；2-methylprop-2-enoyl isothiocyanate
• CAS: 56368-95-7
• 化学式: C₅H₅NOS
• 分子量: 127.167
• InChiKey: VBXSOVVXEAGWRX-UHFFFAOYSA-N

物化性质

• 沸点：
  60 °C(Press: 18 Torr)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methacryloyl isothiocyanate 以 甲苯 为溶剂， 生成 2-anilino-5-methyl-5,6-dihydro-[1,3]thiazin-4-one
  参考文献：
  名称：

  Sineokov,A.P.; Sergeeva,M.E., Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1427 - 1429

  摘要：

  DOI：
• 作为产物：
  描述：

  2-thioxo-[1,3]thiazinan-4-one 、 甲基丙烯酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以30%的产率得到methacryloyl isothiocyanate
  参考文献：
  名称：

  1,3-噻嗪的研究，11. Mitt. 3-Acyl-4-oxo-2-thioxo-tetrahydro-1,3-thiazines，新型环状 N, N-bis-acyl-dithiourethanes

  摘要：

  4-oxo-2-thioxo-tetrahydro-1,3-thiazines 1 和 2 在三乙胺存在下与酰氯反应得到 3-酰基衍生物 3 和 4，并使用水解研究了它们作为转酰基试剂的性质、醇解和氨解为例。

  DOI：

  10.1002/ardp.19803131004

文献信息

• Synthesis and crystal structure of 5-methyl-2-(N-anabasinyl)-5,6-dihydro-1,3-thiazin-4-one from the alkaloid anabasine
  作者：I. V. Kulakov、D. M. Turdybekov

  DOI：10.1007/s10600-010-9681-7

  日期：2010.9

  5-Methyl-2-(N-anabasinyl)-5,6-dihydro-1,3-thiazin-4-one was synthesized in one step from the alkaloid anabasine. Its structure was proved by IR and PMR spectroscopy, mass spectrometry, and an x-ray structure analysis.

  以生物碱新竹碱一步合成了5-甲基-2-(N-新竹碱)-5,6-二氢-1,3-噻嗪-4-酮。其结构通过IR和PMR光谱、质谱和X射线结构分析得到证明。
• Synthesis, Molecular Docking, and Hemorheological Activity of New 4-(Thien-2-yl)-3-aminopyridine-2(1H)-one Derivatives
  作者：I. V. Palamarchuk、Z. T. Shulgau、Sh. D. Sergazy、A. M. Zhulikeeva、T. M. Seilkhanov、I. V. Kulakov

  DOI：10.1134/s1070363222090110

  日期：2022.9

  the basis of 4-(thien-2-yl)-3-aminopyridine-2(1H)-one, the corresponding chloroacetamide and condensed 1H-pyrido[2,3-b][1,4]oxazine-2(3H)-one were synthesized by the reaction of acylation with chloroacetyl chloride. Thioureide derivatives of 3-aminopyridine-2(1H)-one were obtained by reactions with a number of isothiocyanates. It was shown that the carbamothionylmethacrylamide derivative cyclizes rather

  摘要 以4-(thien-2-yl)-3-aminopyridine-2(1 H )-one为基础，得到相应的氯乙酰胺和缩合的1 H- pyrido[2,3 -b ][1,4]oxazine-2 (3H)-one是通过与氯乙酰氯的酰化反应合成的。3-氨基吡啶-2(1 H )的硫脲衍生物)-一种是通过与许多异硫氰酸酯反应获得的。结果表明氨基甲硫基甲基丙烯酰胺衍生物相当容易环化成取代的1,3-噻嗪。进行了用于抗血栓活性的合成衍生物的分子对接，这表明吡啶酮核心中硫脲片段的存在导致对所选蛋白质的亲和力增加。使用增加的血液粘度综合征的体外模型对化合物的血液流变学研究也显示了在参考药物己酮可可碱水平上的活性。
• Synthesis, steric structure, and biological activity of 5-methyl-2-(morpholin-4-ylamino)-5,6-dihydro-4H-1,3-thiazin-4-one
  作者：I. V. Kulakov、Z. T. Shulgau、K. M. Turdybekov、D. M. Turdybekov、D. T. Sadyrbekov

  DOI：10.1134/s1070363215020188

  日期：2015.2

  New 5,6-dihydro-1,3-thiazin-4-one derivatives have been synthesized by one-pot reaction of morpholin-4-amine and adamantan-1-amine with methacryloyl isothiocyanate. Structure of 5-methyl-2-(morpholin-4-ylamino)-5,6-dihydro-4H-1,3-thiazin-4-one has been determined by X-ray analysis, and its high antiradical and anti-inflammatory activity has been revealed.
• Synthesis and Intramolecular Cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea
  作者：I. V. Kulakov、O. S. Nikitina、A. S. Fisyuk、D. S. Goncharov、Z. T. Shul’gau、A. E. Gulyaev

  DOI：10.1007/s10593-014-1519-y

  日期：2014.8

  The reaction of 3-amino-4,6-dimethylpyridin-2(1H)-one and 3-amino-4-phenylpyridin-2-one with acyl isothiocyanates (benzoyl-, 4-bromobenzoyl-, and methacryloyl isothiocyanates) and with allyl isothiocyanate has been studied. The N-carbamothioyl methacrylamides and N-allylthioureas obtained undergo intramolecular heterocyclization reactions to give the corresponding 1,3-thiazin-4-one and 1,3-thiazoline derivatives. It was found that the starting 3-amino-4,6-dimethylpyridin-2(1H)-one shows antiradical activity but the synthesized thioureas do not.
• Acyl isothiocyanate and polymer thereof
  申请人：DU PONT

  公开号：US02327985A1

  公开（公告）日：1943-08-31