(6S,5R)-1-aza-3-oxa-2,2,5-trimethylbicyclo<4.2.0>octan-8-one | 75521-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (6S,5R)-1-aza-3-oxa-2,2,5-trimethylbicyclo<4.2.0>octan-8-one
• 英文别名: (5R,6S)-2,2,5-trimethyl-3-oxa-1-azabicyclo[4.2.0]octan-8-one
• CAS: 75521-16-3
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: ZPHNUVCZAJNBRN-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6S,5R)-1-aza-3-oxa-2,2,5-trimethylbicyclo<4.2.0>octan-8-one 生成 (5R,6S,7S)-7-[(1R)-1-hydroxyethyl]-2,2,5-trimethyl-3-oxa-1-azabicyclo[4.2.0]octan-8-one
  参考文献：
  名称：

  CHRISTENSEN, B. G.;SHIH, D. H.

  摘要：

  DOI：
• 作为产物：
  描述：

  (6S)-1-aza-3-oxa-2,2-dimethyl-4-methylenebicyclo<4.2.0>octan-8-one 在 镍 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 4.0h， 以90%的产率得到(6S,5R)-1-aza-3-oxa-2,2,5-trimethylbicyclo<4.2.0>octan-8-one
  参考文献：
  名称：

  立体控制1β-甲基硫霉素关键中间体的方法

  摘要：

  已经描述了用于1β-甲基硫代霉素的高级中间体（2）的两种立体控制方法。

  DOI：

  10.1016/s0040-4039(00)94390-9

文献信息

• 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。
• Synthetic carbapenem antibiotics II. Stereoisomers of 7-hydroxyethyl-2,2,5-trimethyl-3-oxa-1-azabicyclo[4.2.O]octan-8-one
  作者：David H. Shih、Judith A. Fayter、L.D. Cama、Burton G. Christensen、Jordan Hirshfield

  DOI：10.1016/s0040-4039(00)89153-4

  日期：1985.1

  The titled compounds are key synthetic intermediates in the structure-activity relationship studies of novel 1-methyl carbapenem antibiotics. Preparation and structural determination of these stereoisomers by x-ray crystallography and proton NMR spectroscopy are reported.

  标题化合物是新型1-甲基碳青霉烯抗生素的结构-活性关系研究中的关键合成中间体。报道了通过X射线晶体学和质子NMR光谱法制备和立体确定这些立体异构体。
• Shirai, Masashi; Nishiwaki, Tarozaemon, Journal of Chemical Research, Miniprint, 1990, # 9, p. 2018 - 2031
  作者：Shirai, Masashi、Nishiwaki, Tarozaemon

  DOI：——

  日期：——
• 1β-Methylthienamycin: Some stereocontrolled approaches towards the key intermediate
  作者：Mukund K Gurjar、Manjunath N Bhanu、Vivek B Khare、Ashok Bhandari、Madhusudhan N Deshmukh、A V Rama Rao

  DOI：10.1016/s0040-4020(01)96165-4

  日期：1991.8

  Two stereocontrolled approaches towards a precursor of 1 beta-methyl-thienamycin, have been accomplished by involving stereospecific hydrogenation of 13 and stereoselective hydroboration oxidation of 9. The latter compounds were obtained from the easily accessible chiral building block 7. The hydroboration-oxidation approach was extended to 18 in which the optically active 1R- (1-hydroxy ethyl) side-chain was incorporated. The highly stereoselective hydroboration-oxidation reaction of 9 is explained by considering Houk's models.
• 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.