<2>-Pyridylmercaptoaceton | 3166-26-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: <2>-Pyridylmercaptoaceton
• 英文别名: 1-(Pyridin-2-ylsulfanyl)propan-2-one；1-pyridin-2-ylsulfanylpropan-2-one
• CAS: 3166-26-5
• 化学式: C₈H₉NOS
• mdl: MFCD12145811
• 分子量: 167.232
• InChiKey: RSDVVSQQCVSWNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <2>-Pyridylmercaptoaceton 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (RS)-1-(2-pyridylthio)propan-2-ol
  参考文献：
  名称：

  Kinetic resolution of heteroaryl β-hydroxy sulfides catalyzed by Humicola lanuginosa lipase

  摘要：

  Humicola lanuginosa lipase-catalyzed resolution of heteroaryl substituted beta-hydroxy sulfides by irreversible transesterification using vinyl acetate as acylating agent is discussed. The ee of the resolved alcohols was determined from the H-1 NMR of their corresponding (S)-(+)-O-acetylmandelic acid esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00148-9
• 作为产物：
  描述：

  2-巯基吡啶 、 2,2,6,6-四甲基哌啶氧化物 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以30%的产率得到<2>-Pyridylmercaptoaceton
  参考文献：
  名称：

  使用TEMPO作为C 3合成子，通过顺序氧化，骨架重排和CS键形成的反应级联反应合成α-芳硫基丙酮

  摘要：

  在这里，我们提出了从商业化的硫醇和普遍使用的TEMPO及其类似物到α-亚磺酰基化羰基化合物的空前途径，它们在简单且无金属的条件下通过骨架重排充当C 3合成子。机理研究表明，该反应涉及连续的自由基氧化和阳离子偶联过程。TEMPO类似物和硫醇分别在自由基过程中充当氧化剂和还原剂，而在偶联过程中，前者提供C 3合成子与相关的硫源偶联。

  DOI：

  10.1039/c9ob00018f

文献信息

• Intermediates to prepare pyridazinone herbicides, and a process to prepare them
  申请人：FMC Corporation

  公开号：US10913719B2

  公开（公告）日：2021-02-09

  Disclosed is a process for preparing a compound of Formula 1, from a compound of Formula 2 wherein X, R1, R2, R3, R4, R5, n, R6, R7, G and W are as defined in the disclosure. Also disclosed are compounds of Formulae 2 and 4 wherein X, R1, R2, R3, R4, R5, n, R6, R7, G and W are as defined in the disclosure. Also disclosed is a process for preparing the compounds of Formulae 2 and 4.

  本发明公开了一种制备式 1 化合物的工艺、 其中 X、R1、R2、R3、R4、R5、n、R6、R7、G 和 W 如公开内容中所定义。还公开了式 2 和 4 的化合物 其中 X、R1、R2、R3、R4、R5、n、R6、R7、G 和 W 如本公开中所定义。还公开了一种制备式 2 和 4 的化合物的工艺。
• Access to Central Carbon Chirality through Cycloplatination of 1-(2-Pyridinylthio)propanone by <i>cis</i>-[PtCl₂(<i>S</i>-SOMe(<i>p</i>-tolyl))]. The Crystal Structure of (<i>S</i>_s<i>S</i>_c)-[Pt{py{SCHC(O)Me}-2}Cl(SOMe(<i>p</i>-tolyl))]
  作者：Alexander D. Ryabov、Irina M. Panyashkina、Vladimir A. Polyakov、Andreas Fischer

  DOI：10.1021/om0109399

  日期：2002.4.1

  Cycloplatination of the prochiral sp(3)C-H bond of 1-(2-pyridinylthio)propanone (py(SCH2C(O)Me)(-2), 1a) by cis-[PtCl2(SOMe2)] in dry ethanol affords [Pt(py(SCHC(O)Me)-2)Cl(SOMe2)] (3a) in 77% isolated yield without any side product. The same reaction using the chiral complex cis-[PtCl2(S-SOMe(p-tolyl))] (the absolute configuration of sulfur is indicated for the coordinated ligand) leads to two cycloplatinated diastereoisomers, 4a (SsRc) and 4b (SsSc), in 12.9 and 33.7% yield, respectively (de 44.6%). Their absolute configuration was deduced from the analysis of the H-1 NMR spectra and confirmed by an X-ray structural investigation of 4b. Diastereomer 4b was shown to react with PPh3 to give the enantiomer [Pt(py(SCHC(O)Me)-2)Cl(PPh3)] with the central carbon chirality only. Rather surprisingly, attempted cycloplatination Of py(SCH2C(O)Ph)-2 (1b) by cis-[PtCl2(SOMe2)] affords the cycloplatinated complex [Pt(pyf(SCHC(O)Ph)-2)Cl(SOMe2)] (3b) in a miserable yield.
• Multidonor Ligands. 3. Cyclopalladation of py{SCH₂C(O)R}-2 (py-2 = 2-pyridyl, R = Ph, Me, OMe) through a C(sp³)−H Bond Activation
  作者：José Vicente、María-Teresa Chicote、Concepción Rubio、M. Carmen Ramírez de Arellano、Peter G. Jones

  DOI：10.1021/om981043f

  日期：1999.7.1

  [PdCl2(NCPh)(2)] reacts with R-carbonylmethylenethiopyridines [pySCH2C(O)R}-2] to give, depending on the substituent R and the reaction conditions, [PdpySCHC(O)Ph}-2}(mu-Cl)(2)Pd-pySCH2C(O)Ph}-2}Cl] or the coordination complexes [PdpySCH2C(O)R}-2}(2)Cl-2] (R = Ph, Me, OMe). The latter can be doubly deprotonated by a base (Na2CO3 or NaH) to give dicyclometalated complexes cis-[PdpySCHC(O)R}-2}(2)]. These transmetalate one ligand to [PdCl2(NCPh)(2)] to give [Pdpy(SCHC(O)R}-2}(mu-Cl)](2), which in turn reacts with (Me4N)Cl or with monodentate ligands L or with MeCN in the presence of AgClO4 to give anionic Me4N[PdpySCHC(O)Ph}-2}Cl-2], neutral [Pdpy(SCHC(O)R}-2}Cl(L)] [R = Ph, L = PPh3, pySCH2C(O)Ph}-2, (BuNC)-Bu-t, NH2CH(Me)Ph, pyridine (py), tetrahydrothiophene (tht); R= Me, L = PPh3, py, tht], or cationic [PdpySCHC(O)R}-2}(NCMe)(2)]ClO4 (R = Ph, Me, OMe) complexes, respectively. The latter react with PPh3 or with bidentate ligands to give complexes [PdpySCHC(O)Ph}-2}(NCMe)(PPh3)]ClO4 or [Pd(pySCHC(O)Ph}-2}L-2]ClO4 [L = PPh3, L-2 = N,N,N',N'-tetramethylethylenediamine (tmeda) or 2,2'-bipyridine (bipy)]. The crystal structures of [PdpySCHC(O)R}-2}(2)] and [PdpySCHC(O)R}-2}ClpySCH2C(O)R}2}] have been determined.
• Bradsher,C.K.; Lohr,D.F., Journal of Heterocyclic Chemistry, 1966, vol. 3, p. 27 - 32
  作者：Bradsher,C.K.、Lohr,D.F.

  DOI：——

  日期：——
• Multidonor Ligands. 2.¹ Room-Temperature C(sp³)−H Activation of 2-(Alkylthio)pyridine by Gold(III) Complexes
  作者：José Vicente、María Teresa Chicote、María Isabel Lozano、Sonia Huertas

  DOI：10.1021/om980747m

  日期：1999.2.1

  Na[AuCl4] reacts with [pySCH2C(O)R}-2] (py-2 = 2-pyridyl) at room temperature to give cyclometalated alkylgold(III) complexes [AuCl2pySCHC(O)R}-2}] [R = Ph (1a); Me (1b), OMe (1b)], which in turn react with NaBr or with PR'(3) in the presence of NaClO4 to give [AuBr2pySCHC(O)R}-2}] [R = Ph (2a), Me (2b)] or a mixture of SP4-3- and SP4-4-[AuCl-pySCHC(O)R}-2}(PPh3)]ClO4 [R = Ph (3a), Me (3b)]. This mixture of isomers converted to the isomer SP4-4 upon refluxing in chloroform. When the last reaction was made using P(C6H4OMe-4)(3), the main products were [AuClP(C6H4OMe-4)(3)}] and [HpySCH2C(O)Ph}2]ClO4. The crystal structure of the latter has been determined.