S-2-pyridyl acetoxythioacetate | 141685-06-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-2-pyridyl acetoxythioacetate
• 英文别名: 2-Pyridylthio(acetoxy)acetate；(2-Oxo-2-pyridin-2-ylsulfanylethyl) acetate
• CAS: 141685-06-5
• 化学式: C₉H₉NO₃S
• 分子量: 211.241
• InChiKey: DIUAESPLHMFFPU-UHFFFAOYSA-N

物化性质

• 沸点：
  338.0±22.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  81.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-2-pyridyl acetoxythioacetate 、 [(S)-2-(tert-Butyl-dimethyl-silanyloxy)-prop-(E)-ylidene]-(4-methoxy-phenyl)-amine 在 四氯化钛 、 三乙胺 作用下， 生成 Acetic acid (2R,3S)-2-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-3-yl ester
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines

  摘要：

  A mild and versatile one-pot synthesis of beta-lactams has been performed by condensation of the easily generated titantium enolates of 2-pyridyl thioesters with imines employing chiral reaction partners. Both imines obtained from enantiomerically pure alkoxy aldehydes and the enolate derived from 3-hydroxybutyrate showed high diastereofacial preferences, efficiently transferring the stereochemical information to the stereocenters of the azetidinone ring. Advanced precursors of (+)-PS-5, (+)-PS-6, thienamycin, and 1-beta-methylthienamycin were prepared to illustrate the potential of this method. A H-1-NMR study of the enolization process and a tentative rationalization of the stereochemical results are presented.

  DOI：

  10.1021/jo00041a019
• 作为产物：
  描述：

  2-巯基吡啶 、 乙酰氧基乙酰氯 以89%的产率得到S-2-pyridyl acetoxythioacetate
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines

  摘要：

  A mild and versatile one-pot synthesis of beta-lactams has been performed by condensation of the easily generated titantium enolates of 2-pyridyl thioesters with imines employing chiral reaction partners. Both imines obtained from enantiomerically pure alkoxy aldehydes and the enolate derived from 3-hydroxybutyrate showed high diastereofacial preferences, efficiently transferring the stereochemical information to the stereocenters of the azetidinone ring. Advanced precursors of (+)-PS-5, (+)-PS-6, thienamycin, and 1-beta-methylthienamycin were prepared to illustrate the potential of this method. A H-1-NMR study of the enolization process and a tentative rationalization of the stereochemical results are presented.

  DOI：

  10.1021/jo00041a019

文献信息

• 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。
• Synthesis of β-lactams by condensation of the tin enolates of 2-pyridylthioesters with imines. A comparison between titanium and tin enolates
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1016/s0040-4020(01)85649-0

  日期：1994.1

  SnBr4 affords the corresponding tin(IV) enolates that add to imines to give β-lactams in fair to good yields and with various degree of trans/cis stereoselectivity. Examples of highly diastereofacially selective reactions carried out on a chiral thioester and on a chiral imine are also reported. The results are compared with those obtained in the condensations promoted by TiCl4 and TiBr4.

  将三乙胺加到2-吡啶基硫代酯和SnCl 4或SnBr 4的混合物中，得到相应的锡（IV）烯醇盐，它们加到亚胺上，以公平至良好的收率和不同程度的反式/顺式立体选择性得到β-内酰胺。还报道了在手性硫酯和手性亚胺上进行的高度非对映选择性反应的实例。将结果与由TiCl 4和TiBr 4促进的缩合中获得的结果进行比较。
• Stereoselective one-pot synthesis of β-lactams by reaction of 2-pyridylthioesters with imines in the presence of AlBr3 or EtAlCl2
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Oscar Martini、Valentina Molteni

  DOI：10.1016/0040-4020(95)01087-4

  日期：1996.2

  The reactions of some 2-pyridylthioesters with imines in the presence of AlBr3 or EtAlCl2 and of a tertiary amine afford β-lactams in a simple one-pot procedure with fair to high trans stereoselectivity. The condensation can be also carried out in the absence of base and with sub-stoicheiometric amounts of the Lewis acid. The possible mechanisms of the process are discussed.

  在AlBr 3或EtAlCl 2存在下，某些2-吡啶基硫代酯与亚胺的反应和叔胺可通过简单的一锅法以中等至高的反式立体选择性提供β-内酰胺。缩合反应也可以在不存在碱和亚化学计量量的路易斯酸的条件下进行。讨论了该过程的可能机制。
• Optically Active Aminoalcohol Promoted Addition of 2-Pyridylthioester Boron Enolates to Imines: Enantioselective One-pot Synthesis of β-Lactams
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Valentina Molteni、Laura Raimondi

  DOI：10.1016/0040-4020(95)00503-z

  日期：1995.8

  The enolates derived from 2-pyridylthioesters by treatment with BCl3 . Me(2)S and enantiomerically pure aminoalcohols react with aromatic and heteroaromatic imines to afford beta-lactams in a convenient one-pot procedure and in up to 78% e.e. The aminoalcohol can be employed both as the metal ligand and as the base to generate the enolate. Among several aminoalcohols tested, N-methylephedrine turned our to be the more efficient in terms of stereoselectivity.
• Efficient and highly stereoselective synthesis of a β-Lactam inhibitor of the serine protease prostate-specific antigen
  作者：R Annunziata

  DOI：10.1016/s0968-0896(02)00017-2

  日期：2002.6

  An efficient synthesis of a beta-lactam precursor of the serine protease, prostate-specific antigen inhibitor 1 has been accomplished. The synthesis relies on two completely stercoselective reactions that allow the introduction of the stereocenters at C-3 and C-4 of the azetidinone ring in a predictable manner. (C) 2002 Elsevier Science Ltd. All rights reserved.