1-[(2-pyrimidyl)thio]-2-propanone | 250690-52-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-[(2-pyrimidyl)thio]-2-propanone
• 英文别名: 2-(acetonylthio)pyrimidine；1-pyrimidin-2-ylsulfanyl-propan-2-one；2-Acetonylmercapto-pyrimidin；1-Pyrimidin-2-ylsulfanylpropan-2-one
• CAS: 250690-52-9
• 化学式: C₇H₈N₂OS
• mdl: MFCD09053597
• 分子量: 168.219
• InChiKey: SFHYCOCBXUJVRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(2-pyrimidyl)thio]-2-propanone 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙二醇二甲醚 为溶剂， 以78%的产率得到1-fluoro-1-[(2-pyrimidyl)thio]-2-propanone
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 35.¹ Anodic Fluorination of 2-Pyrimidyl, 2-Pyridyl, and 2-Quinazolinonyl Sulfides

  摘要：

  Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron(EWG) withdrawing group at the position alpha to the sulfur atom was successfully carried out using Et4NF . nHF (n = 3, 4) or Et3N . 3HF as a supporting electrolyte and a fluoride ion source in 1,2-dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2-(fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with alpha,alpha-difluorinated product. In contrast, the corresponding 2-quinazolinonyl sulfides underwent similarly alpha-fluorination along with unexpected ipso-fluorination through anodic desulfurization.

  DOI：

  10.1021/jo9909857
• 作为产物：
  描述：

  一氯丙酮 、 2-巯基嘧啶 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到1-[(2-pyrimidyl)thio]-2-propanone
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 35.¹ Anodic Fluorination of 2-Pyrimidyl, 2-Pyridyl, and 2-Quinazolinonyl Sulfides

  摘要：

  Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron(EWG) withdrawing group at the position alpha to the sulfur atom was successfully carried out using Et4NF . nHF (n = 3, 4) or Et3N . 3HF as a supporting electrolyte and a fluoride ion source in 1,2-dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2-(fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with alpha,alpha-difluorinated product. In contrast, the corresponding 2-quinazolinonyl sulfides underwent similarly alpha-fluorination along with unexpected ipso-fluorination through anodic desulfurization.

  DOI：

  10.1021/jo9909857

文献信息

• Alpha- and beta-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
  申请人：Vazquez L. Michael

  公开号：US20070078173A1

  公开（公告）日：2007-04-05

  α- and β-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.

  α-和β-氨基酸羟乙基氨磺酰胺化合物可作为逆转录病毒蛋白酶抑制剂，特别是作为HIV蛋白酶的抑制剂。
• ALPHA- AND BETA-AMINO ACID HYDROXYETHYLAMINO SULFONAMIDES USEFUL AS RETROVIRAL PROTEASE INHIBITORS
  申请人：Vazquez Michael L.

  公开号：US20090023664A1

  公开（公告）日：2009-01-22

  α- and β-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.

  α-和β-氨基酸羟乙基氨磺酰胺化合物是有效的逆转录病毒蛋白酶抑制剂，特别是作为HIV蛋白酶的抑制剂。
• Mass Labels
  申请人：Hamon Christian

  公开号：US20100178710A1

  公开（公告）日：2010-07-15

  A mass label for labelling and detecting a biological molecule by mass spectroscopy, which label comprises the following structure: X-L-M wherein X is a mass marker moiety comprising the following group: formula (I), wherein the cyclic unit is aromatic or aliphatic and comprises from 0-3 double bonds independently between any two adjacent atoms; each Z is independently N, N(R 1 ), C(R 1 ), CO, CO(R 1 ), C(R 1 ) 2 , O or S; X is N, C or C(R 1 ); each R 1 is independently H, a substituted or unsubstituted straight or branched C 1 -C 6 alkyl group, a substituted or unsubstituted aliphatic cyclic group, a substituted or unsubstituted aromatic group or a substituted or unsubstituted heterocyclic group; and y is an integer from 0-10, L is a cleavable linker comprising an amide bond and M is a mass normalization moiety.

  一种用于质谱法标记和检测生物分子的质量标记，该标记包括以下结构：X-L-M，其中X是质量标记基团，包括以下组：公式（I），其中环状单元是芳香族或脂肪族，并且在任意两个相邻原子之间独立地包含0-3个双键；每个Z独立地是N，N（R1），C（R1），CO，CO（R1），C（R1）2，O或S；X为N，C或C（R1）；每个R1独立地是H，取代或未取代的直链或支链C1-C6烷基，取代或未取代的脂肪环状基团，取代或未取代的芳香族基团或取代或未取代的杂环基团；y为0-10的整数，L是一个可断链的连接基团，包括一个酰胺键，M是一个质量归一化基团。
• Bradsher,C.K.; Lohr,D.F., Journal of Heterocyclic Chemistry, 1967, vol. 4, p. 75 - 79
  作者：Bradsher,C.K.、Lohr,D.F.

  DOI：——

  日期：——
• Direct Synthesis of α-Sulfenylated Ketones under Electrochemical Conditions
  作者：Aline A. N. de Souza、Aloisio de A. Bartolomeu、Timothy J. Brocksom、Timothy Noël、Kleber T. de Oliveira

  DOI：10.1021/acs.joc.2c00147

  日期：2022.5.6