ox-glycyl chloride | 61964-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ox-glycyl chloride
• 英文别名: 4,5-Diphenyl-2-oxo-4-oxazolin-3-yl-acetylchlorid；3(2H)-Oxazoleacetyl chloride, 2-oxo-4,5-diphenyl-；2-(2-oxo-4,5-diphenyl-1,3-oxazol-3-yl)acetyl chloride
• CAS: 61964-71-4
• 化学式: C₁₇H₁₂ClNO₃
• 分子量: 313.74
• InChiKey: FUUJJKKLRGGIKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ox-glycyl chloride 在 三氯化铁 、 戴斯-马丁氧化剂 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 6.33h， 生成 (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Enantioselective Total Syntheses of [6R,7R] and [6S,7S] Tricyclic β-Lactams

  摘要：

  The reaction of Ox-glycyl chloride with a chiral imine derived from the combination of D-(R)-glyceraldehyde acetonide and protected D-threonine afforded optically active, highly functionalized cis-substituted beta-lactams 11 and 12. These beta-lactams provide versatile intermediates for the syntheses of biologically important carbacephalosporins, isooxacephems, and other multicyclic beta-lactams. Desilylation and oxidation of 12 with Dess-Martin periodinane followed by intramolecular cyclization produced a novel tricyclic beta-lactam 17 and a 1-(hydroxymethyl)-O-2-isocephem 18 with [6R,7R] absolute configuration. Removal of the Ox protecting group and acylation of 17 in a one-pot reaction followed by saponification furnished the target salt 24. Alternatively, reaction of phthaloylglycyl chloride with the chiral imine derived from the combination of L-(S)-glyceraldehyde acetonide and protected D-threonine gave only one enantiomeric azetidinone 27 in high yield. Further manipulation of 27 provided a new tricyclic beta-lactam 39 with [6S,7S] absolute configuration which satisfies the stereochemistry typically required for antibacterial activity, This synthetic procedure provides a short, versatile and enantioselective method of preparing polycyclic beta-lactams. Biological testing of these tricyclic beta-lactams indicated that salt 39 has potential inhibitory activity against four typical strains of bacteria.

  DOI：

  10.1021/jo951651u
• 作为产物：
  描述：

  3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 ox-glycyl chloride
  参考文献：
  名称：

  Substituted azetidinones

  摘要：

  公开了用于制备具有抗菌活性的新型双环β-内酰胺青霉素类似物的替代氮杂环丙烷中间体。

  公开号：

  US04200572A1

文献信息

• 8-Oxo-4-thia-1-azabicyclo (4.2.0)-oct-2-ene derivatives
  申请人：SmithKline Corporation

  公开号：US04103086A1

  公开（公告）日：1978-07-25

  Novel bicyclic .beta.-lactams and intermediates useful in their preparation are disclosed. In particular, 7.beta.-acyl-amino- and 7.beta.-amino-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acids are prepared. The acylated compounds are antibacterial agents.

  披露了新型的双环β-内酰胺和其在制备中有用的中间体。特别是，制备了7β-酰氨基-和7β-氨基-8-氧代-4-噻-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸。这些酰化化合物是抗菌剂。
• Methods and intermediates for preparing cis-4-oxoazetidine intermediates
  申请人：SmithKline Corporation

  公开号：US04166816A1

  公开（公告）日：1979-09-04

  The stereospecific cycloaddition of nitrogen containing acetic acid halides or anhydrides with Schiff bases having a carbalkoxy group substituted on the methine carbon atom offers new intermediates and methods for preparing synthetic cephalosporin congeners having antibacterial activity.

  含有氮的醋酸卤化物或酐与在次甲基碳原子上带有羧烷氧基团的希夫碱进行立体特异性环加成反应，为合成具有抗菌活性的头孢菌素同类物提供了新的中间体和方法。
• Cis-4-oxoazetidine intermediates and methods of preparing them
  申请人：SmithKline Corporation

  公开号：US04072674A1

  公开（公告）日：1978-02-07

  The stereospecific cycloaddition of nitrogen containing acetic acid halides or anhydrides with Schiff bases having a carbalkoxy group substituted on the methine carbon atom offers new intermediates and methods for preparing synthetic cephalosporin congeners having antibacterial activity.

  含氮的醋酸卤化物或酐与在次甲基碳原子上带有羧烷氧基团的希夫碱进行立体特异性环加成，提供了新的中间体和方法，用于制备具有抗菌活性的合成头孢菌素同类物。
• Substituted azetidinones
  申请人：SmithKline Corporation

  公开号：US04200572A1

  公开（公告）日：1980-04-29

  Substituted azetidine intermediates for preparing novel bicyclic .beta.-lactam penicillin analogs which have antibacterial activity are disclosed.

  公开了用于制备具有抗菌活性的新型双环β-内酰胺青霉素类似物的替代氮杂环丙烷中间体。
• 7-Acylamino-8-oxo-3-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid
  申请人：SmithKline Corporation

  公开号：US04089956A1

  公开（公告）日：1978-05-16

  A new series of 7-acylamino-8-oxo-3-oxa-1-azabicyclo-[4.2.0]octane-2-carboxylic acid derivatives is described which compounds have antibacterial activity especially against certain Gram negative organisms.

  描述了一系列新的7-酰胺基-8-酮基-3-氧杂-1-氮杂双环[4.2.0]辛烷-2-羧酸衍生物，这些化合物具有抗细菌活性，特别针对某些革兰氏阴性微生物。