methyl-3-oxo-3-(pyridine-4-yl)propanedithioate | 1228956-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-3-oxo-3-(pyridine-4-yl)propanedithioate
• 英文别名: Methyl 3-oxo-3-pyridin-4-ylpropanedithioate
• CAS: 1228956-84-0
• 化学式: C₉H₉NOS₂
• 分子量: 211.309
• InChiKey: UKIFAMYBNOJRMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl-3-oxo-3-(pyridine-4-yl)propanedithioate 在 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以81%的产率得到3-(methylthio)-5-(pyridin-4-yl)isoxazole
  参考文献：
  名称：

  Divergent Reactivity in the Reaction of β-Oxodithioesters and Hydroxylamine: Access to β-Ketonitriles and Isoxazoles

  摘要：

  Starting from beta-oxodithioesters and hydroxylamine, two completely different transformations afford either beta-ketonitriles or isoxazoles with high chemoselectivity depending on the reaction conditions. The reaction of beta-oxodithioesters with hydroxylamine in EtOH at room temperature in daylight gave beta-ketonitriles in high yields. On the other hand, 3-methylthio-isoxazoles were efficiently obtained as the final products by heating the mixture of beta-oxodithioesters and hydroxylamine in HOAc at 90 degrees C.

  DOI：

  10.1021/acs.joc.5b01869
• 作为产物：
  描述：

  4-乙酰吡啶 、 三硫代碳酸二甲酯 在 sodium hydride 作用下， 以 苯 为溶剂， 生成 methyl-3-oxo-3-(pyridine-4-yl)propanedithioate
  参考文献：
  名称：

  Novel 3-alkanoyl/aroyl/heteroaroyl-2H-chromene-2-thiones: Synthesis and evaluation of their antioxidant activities

  摘要：

  A facile, convenient and high yielding synthesis of a combinatorial library of 3-alkanoyl/aroyl/heteroaroyl-2H-chromene-2-thiones has been developed by the condensation of easily accessible beta-oxodithioesters and salicylaldehyde/substituted 2-hydroxybenzaldehydes under solvent-free conditions. The assessment of radical scavenging capacity of the compounds towards the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured and these compounds were found to scavenge DPPH free radical efficiently. Five selected compounds were able to protect curcumin from the attack of sulfur free radical generated by radiolysis of glutathione (GSH). The newly synthesized compounds exhibited profound antioxidant activities Five of them rendered comparatively high antioxidant capacity.

  DOI：

  10.1016/j.ejmech.2010.01.070

文献信息

• An Efficient One-Pot Regioselective Approach Towards the Synthesis of Thiopyrano[2,3-<i>d</i>]thiazole-2-thiones Catalyzed by Basic Ionic Liquid under Microwave Irradiation
  作者：I. R. Siddiqui、Arjita Srivastava、Shayna Shamim、Anjali Srivastava、Shireen、Malik A. Waseem

  DOI：10.1002/jhet.2314

  日期：2016.5

  A green, regioselective protocol for the synthesis of thiopyrano[2,3‐d]thiazole‐2‐thiones catalyzed by basic ionic liquid [bmIm]OH has been developed. The reaction proceeds smoothly under microwave irradiation, and high yields of the products are obtained in very short reaction times (5–11 min). The ionic liquid plays a dual solvent‐catalyst role.

  已经开发了一种绿色的区域选择性方案，用于在碱性离子液体[bmIm] OH催化下合成噻吩并[2,3 - d ]噻唑-2-硫酮。在微波辐射下，反应可顺利进行，并且在很短的反应时间（5-11分钟）内即可获得高产率的产物。离子液体起着双重溶剂催化剂的作用。
• Devi, Nepram Sushuma; Singh, Thokchom Prasanta; Khumanthem, Nonibala, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 9, p. 1224 - 1231
  作者：Devi, Nepram Sushuma、Singh, Thokchom Prasanta、Khumanthem, Nonibala、Singh, Okram Mukherjee

  DOI：——

  日期：——
• Divergent Reactivity in the Reaction of β-Oxodithioesters and Hydroxylamine: Access to β-Ketonitriles and Isoxazoles
  作者：Jiaheng Li、Wei Ma、Wenbo Ming、Cong Xu、Na Wei、Mang Wang

  DOI：10.1021/acs.joc.5b01869

  日期：2015.11.6

  Starting from beta-oxodithioesters and hydroxylamine, two completely different transformations afford either beta-ketonitriles or isoxazoles with high chemoselectivity depending on the reaction conditions. The reaction of beta-oxodithioesters with hydroxylamine in EtOH at room temperature in daylight gave beta-ketonitriles in high yields. On the other hand, 3-methylthio-isoxazoles were efficiently obtained as the final products by heating the mixture of beta-oxodithioesters and hydroxylamine in HOAc at 90 degrees C.
• Novel 3-alkanoyl/aroyl/heteroaroyl-2H-chromene-2-thiones: Synthesis and evaluation of their antioxidant activities
  作者：Okram Mukherjee Singh、Nepram Sushuma Devi、Dhanaraj Singh Thokchom、Gurumayum Jitendra Sharma

  DOI：10.1016/j.ejmech.2010.01.070

  日期：2010.6

  A facile, convenient and high yielding synthesis of a combinatorial library of 3-alkanoyl/aroyl/heteroaroyl-2H-chromene-2-thiones has been developed by the condensation of easily accessible beta-oxodithioesters and salicylaldehyde/substituted 2-hydroxybenzaldehydes under solvent-free conditions. The assessment of radical scavenging capacity of the compounds towards the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured and these compounds were found to scavenge DPPH free radical efficiently. Five selected compounds were able to protect curcumin from the attack of sulfur free radical generated by radiolysis of glutathione (GSH). The newly synthesized compounds exhibited profound antioxidant activities Five of them rendered comparatively high antioxidant capacity.