4(S)-4-<(1R)-(1-hydroxymethyl)ethyl>azetidin-2-one | 130609-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4(S)-4-<(1R)-(1-hydroxymethyl)ethyl>azetidin-2-one
• 英文别名: (4R)-<(R)-1-(hydroxymethyl)ethyl>azetidine-2-one；(4R)-4-[(2R)-1-hydroxypropan-2-yl]azetidin-2-one
• CAS: 130609-06-2
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: BWMRFFJBRCEWGR-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4(S)-4-<(1R)-(1-hydroxymethyl)ethyl>azetidin-2-one 、 2,2-二甲氧基丙烷 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (5R,6R)-2,2,5-Trimethyl-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one
  参考文献：
  名称：

  A simple route to the key intermediate of 1β-methylthienamycin

  摘要：

  A short and straightforward synthetic strategy towards the key intermediate 2 of 1-beta-methylthienamycin has been described.

  DOI：

  10.1016/s0957-4166(00)80047-6
• 作为产物：
  描述：

  (R,E)-ethyl 5-(tert-butyldimethylsilyl)oxy-4-methyl-2-pentenoate 在 palladium on activated charcoal 盐酸 、 三甲基氯硅烷 、 叔丁基氯化镁 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 60.0h， 生成 4(S)-4-<(1R)-(1-hydroxymethyl)ethyl>azetidin-2-one
  参考文献：
  名称：

  A simple route to the key intermediate of 1β-methylthienamycin

  摘要：

  A short and straightforward synthetic strategy towards the key intermediate 2 of 1-beta-methylthienamycin has been described.

  DOI：

  10.1016/s0957-4166(00)80047-6

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。
• Chelation controlled aldol additions of the enolsilane derived from tert-butyl thioacetate : a stereosetective approach to 1β-methylthienamycin
  作者：Cesare Gennari、Pier Giorgio Cozzi

  DOI：10.1016/s0040-4020(01)81455-1

  日期：1988.1

  The tert-butyldimethylenolsilane derived from tert-butyl thioacetate is a useful reagent for highly stereoselective chelation-controlled additions to chiral α-alkoxy and α-methyl-β-alkoxy aldehydes where the corresponding acetate fails. The aldol product deriving from the TiCl4 mediated addition to α-methyl-β-alkoxy aldehyde 5 was elaborated In high yield to give the bicyclic β-lactam 11, an Intermediate

  衍生自硫代乙酸叔丁酯的叔丁基二甲基烯醇硅烷是用于手性α-烷氧基和α-甲基-β-烷氧基醛类（其中相应的乙酸酯失效）的高度立体选择性螯合控制加成的有用试剂。高产率地制备了由TiCl 4介导的加成至α-甲基-β-烷氧基醛5的醛醇产物，得到双环β-内酰胺11，其为制备1β-甲基噻吩霉素的中间体。TiCl 4介导的缩合过程中与醛5的部分消旋化有关的问题尚未完全解决。
• Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Pier Giorgio Cozzi

  DOI：10.1021/jo00041a019

  日期：1992.7

  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.
• Shirai, Masashi; Nishiwaki, Tarozaemon, Journal of Chemical Research, Miniprint, 1990, # 9, p. 2018 - 2031
  作者：Shirai, Masashi、Nishiwaki, Tarozaemon

  DOI：——

  日期：——
• A simple route to the key intermediate of 1β-methylthienamycin
  作者：A V Rama Rao、M K Gurjar、B Ashok

  DOI：10.1016/s0957-4166(00)80047-6

  日期：1991.1

  A short and straightforward synthetic strategy towards the key intermediate 2 of 1-beta-methylthienamycin has been described.