2-thiopyridyl phenylacetate | 61049-78-3

• 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-thiopyridyl phenylacetate
• 英文别名: S-pyridin-2-yl 2-phenylethanethioate；Phenylacetyl-2-pyridyl-thioether；Benzeneethanethioic acid, S-2-pyridinyl ester
• CAS: 61049-78-3
• 化学式: C₁₃H₁₁NOS
• 分子量: 229.302
• InChiKey: QASAANICPWZNBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  388.0±25.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-thiopyridyl phenylacetate 在 四氯化钛 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 1.0h， 生成 anti,anti-3,4,5-triphenyl-2-pyrrolidinone
  参考文献：
  名称：

  通过顺式和反式β-内酰胺衍生物的扩环立体定向制备γ-内酰胺衍生物：β-内酰胺衍生物的α-取代作用

  摘要：

  各种取代的γ-内酰胺衍生物是通过相应的β-内酰胺衍生物的扩环立体定向制备的。系统研究了C-3上带有芳基和烷基取代基的γ-内酰胺的立体化学。前者在C-3上具有苯基或噻吩基，显示出单一的抗γ-内酰胺非对映异构体。后者在C-3上具有甲基或乙基，已显示出抗γ-内酰胺和反γ-内酰胺非对映异构体。

  DOI：

  10.1002/bkcs.10697

文献信息

• Reaction of lithium dialkylcuprates with S-2-pyridyl thioates in the presence of oxygen. A carboxylic ester synthesis
  作者：Sunggak Kim、Jae In Lee、Bong Young Chung

  DOI：10.1039/c39810001231

  日期：——

  Reaction of lithium dialkylcuprates with S-2-pyridyl thioates in the presence of oxygen affords carboxylic esters in high yields, whereas under nitrogen it affords ketones.

  在氧存在下，二烷基铜锂锂与S -2-吡啶基硫代硫酸盐的反应以高收率提供羧酸酯，而在氮气氛下则提供酮。
• 3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
  作者：Sergio Rossi、Tiziana Benincori、Laura Maria Raimondi、Maurizio Benaglia

  DOI：10.1055/s-0039-1690777

  日期：2020.4

  This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride)

  该帐户总结了新的双杂芳族手性双膦氧化物的开发。3,3'-联噻吩基氧化膦 (BITIOPO) 已成功用作有机催化剂，以促进路易斯碱催化、路易斯酸介导的立体选择性转化。这些高度富电子的化合物与三氯甲硅烷基衍生物（烯丙基三氯硅烷和四氯化硅）结合，生成高价硅物质，在高度非对映选择性和对映选择性有机反应中充当手性路易斯酸。详细讨论了与这些应用程序相关的几个相关示例。
• Phosphine Oxide Catalyzed, Tetrachlorosilane-Mediated Enantioselective Direct Aldol Reactions of Thioesters
  作者：Sergio Rossi、Rita Annunziata、Franco Cozzi、Laura Raimondi

  DOI：10.1055/s-0034-1379914

  日期：——

  The stereoselective direct aldol reaction of S-phenyl thioesters and aromatic aldehydes promoted by tetrachlorosilane was realized for the first time; the proposed mechanism involves the formation of a chiral cationic hypervalent silicon species and requires the presence of catalytic amounts of a Lewis base, like a chiral phosphine oxide. The reaction affords syn -hydroxy thioesters as major isomers in good yields, high diastereoselectivity (up to 99:1), and up to 92% enantiomeric excess. The absolute configuration of the major isomer was established by converting the product into the corresponding -hydroxy ester. The scope of the reaction was also investigated by employing differently substituted thioesters in combination with different aromatic aldehydes.
• Stereoselective Synthesis of α- and β-Glycosylamide Derivatives from Glycopyranosyl Azides via Isoxazoline Intermediates
  作者：Fehmi Damkaci、Philip DeShong

  DOI：10.1021/ja028694u

  日期：2003.4.1

  Treatment of 2-acetoxy glycopyranosyl azides with Ph3P gave isoxazolines by ring closure of the phosphorimine. Coupling of in situ generated isoxazolines with acylating reagents gave mixtures of alpha- or beta-glycopyranosyl amides. The alpha/beta ratio depended upon the acylating reagent and metal salts employed. For example, coupling of isoxazoline 3 with Z-Asp-(SPy)-OBn in the presence of CuCl2 gave exclusively alpha-N-glucopyranosylasparagine derivative 8. This general procedure has been applied to mono-, di-, and trisaccharide systems.
• KIM, SUNGGAK;LEE, JAE, IN;CHUNG, BONG, YOUNG, J. CHEM. SOC. CHEM. COMMUN., 1981, N 23, 1231-1232
  作者：KIM, SUNGGAK、LEE, JAE, IN、CHUNG, BONG, YOUNG

  DOI：——

  日期：——