S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate | 139007-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate
• 英文别名: S-2-pyridylbenzyloxythioacetate；S-Pyridin-2-yl 2-(benzyloxy)ethanethioate；S-pyridin-2-yl 2-phenylmethoxyethanethioate
• CAS: 139007-45-7
• 化学式: C₁₄H₁₃NO₂S
• 分子量: 259.329
• InChiKey: VZOQZUVHDCLFJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  399.1±27.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate 在 sodium tetrahydroborate 、 sodium periodate 、 TEA 、 四氯化钛 、 三氟乙酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 9.5h， 生成 (+)-(3R,4S)-1-(4-methoxyphenyl)-3-benzyloxy-4-hydroxymethyl-2-azetidinone
  参考文献：
  名称：

  Stereoselective synthesis of azetidin-2-ones, precursors of biologically active syn-3-amino-2-hydroxybutanoic acids

  摘要：

  DOI：

  10.1021/jo00069a048
• 作为产物：
  描述：

  2-巯基吡啶 、 苄氧基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate
  参考文献：
  名称：

  Mild and convenient one-pot synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines.

  摘要：

  Treatment of 2-pyridylthioesters with triethylamine in the presence of titanium tetrachloride affords titanium enolates that add to imines to give beta-lactams in fair to excellent yields with moderate to good stereoselectivity.

  DOI：

  10.1016/s0040-4020(01)96198-8

文献信息

• Stereoselective synthesis of β-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines bearing a chiral auxiliary
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1016/s0040-4020(01)85521-6

  日期：——

  tested as chiral auxiliaries in the stereoselective synthesis of β-lactams by condensation of the titanium enolates of 2-pyridyl thioesters with chiral imines. The amines were selected among the following classes of compounds: benzylic amines, β-aminoalcohols, β-heterosubstituted α-aminoesters. Inexpensive and available in both enantiomeric forms α-methylbenzylamine was identified as the chiral auxiliary

  通过2-吡啶基硫酯的烯醇钛与手性亚胺的缩合，β-内酰胺的立体选择性合成中已测试了几种胺作为手性助剂。胺选自以下化合物：苄基胺，β-氨基醇，β-杂取代的α-氨基酯。廉价且可以两种对映体形式获得的α-甲基苄胺被鉴定为手性助剂，通常结合了良好的反应性和令人满意的立体控制水平。为了说明该方法的潜力，制备了肾素抑制剂成分的前体。介绍了立体化学结果的初步合理化。
• Construction of Quaternary Stereogenic Centers via [2 + 2] Cycloaddition Reactions. Synthesis of Homochiral 4,4-Disubstituted 2-Azetidinones and Imine Substituent Effects on β-Lactam Formation
  作者：Claudio Palomo、Jesus M. Aizpurua、Jesus M. García、Regina Galarza、Marta Legido、Raquel Urchegui、Pascual Román、Antonio Luque、Juan Server-Carrió、Anthony Linden

  DOI：10.1021/jo962017z

  日期：1997.4.1

  A study on the asymmetric construction of quaternary stereogenic centers via [2 + 2] cycloaddition reaction of ketenes with ketimines is described. Reaction of achiral ketenes and chiral alpha-alkoxy ketone-derived imines resulted in formation of new beta-lactams as single diastereomers. The cycloaddition was extended to pyruvate imines, aralkyl ketone-derived imines, and dialkyl ketimines. In these

  描述了通过烯酮与酮亚胺的[2 + 2]环加成反应对四元立体异构中心进行不对称构建的研究。非手性烯酮与手性α-烷氧基酮衍生的亚胺的反应导致形成新的β-内酰胺类单一非对映异构体。环加成反应扩展到丙酮酸亚胺，芳烷基酮衍生的亚胺和二烷基酮亚胺。在这些情况下，使用β-甲硅烷基链烷酮烯酮和Evans-Sjögren烯酮可以令人满意地实现不对称诱导。衍生自可烯醇化二烷基酮的C，C-双（三甲基甲硅烷基）甲胺酮亚胺干净地导致相应的C（4）二取代的β-内酰胺不去质子化。因此，提供了一种聚合的不对称合成β-内酰胺的通用方法，其中C（4）作为季碳存在。
• Enantioselective one-pot synthesis of β-lactams from achiral 2-pyridylthioesters and aromatic imines
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi

  DOI：10.1016/0040-4039(94)02316-4

  日期：1995.1

  The enolates derived from 2-pyridylthioesters by reaction with BCl3 ·SMe2 and enantiomerically pure aminoalcohols react with aromatic imines in an enantioselective fashion (ee up to 78%) to afford β-lactams in a convenient one-pot procedure.

  通过与BCl 3 ·SMe 2和对映体纯的氨基醇反应而衍生自2-吡啶基硫酯的烯醇化物与芳香亚胺以对映选择性的方式反应（ee高达78％），以方便的一锅法制得β-内酰胺。
• Highly diastereoselective synthesis of β-lactams by addition of titanium enolates of 2-pyridyl thioesters to chiral imines
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Pier Giorgio Cozzi

  DOI：10.1016/s0040-4039(00)91874-4

  日期：1992.2

  Addition of titanium enolates of 2-pyridyl thioesters to chiral imines derived from alkoxy aldehydes occurs with good diastereofacial control, and opens a simple access to important carbapenem antibiotics.

  将2-吡啶基硫酯的钛烯醇盐添加到衍生自烷氧基醛的手性亚胺中，可以很好地控制非对映表面，从而轻松获得重要的碳青霉烯类抗生素。
• PEG-supported pyridylthioesters for racemization-free amide synthesis: a reagent that allows simultaneous product formation and removal from the polymer
  作者：Maurizio Benaglia、Stefania Guizzetti、Clara Rigamonti、Alessandra Puglisi

  DOI：10.1016/j.tet.2005.07.111

  日期：2005.12

  modified poly(ethylene glycol) of Mw 5000 Da have been prepared in high yields. The thioesters were employed as a convenient starting material for the liquid-phase synthesis of various enantiomerically pure amides. This new methodology allowed to perform simultaneously the reaction with the poly(ethylene glycol)-supported reagent and the traceless removal of the final product from the polymer support in

  的锚定到一个改性聚（乙二醇）Pyridylthioesters中号瓦特5000Da的已经以高收率制备。硫代酯被用作液相合成各种对映体纯的酰胺的方便的起始原料。这种新的方法可以在一个步骤中同时进行与聚（乙二醇）负载的试剂的反应，并最终从聚合物载体中无痕地去除最终产物。以高产率和高纯度获得产物。