6,6-Dibromopenicillanic acid 1,1-dioxide methyl ester | 61657-19-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6,6-Dibromopenicillanic acid 1,1-dioxide methyl ester
• 英文别名: Methyl 6,6-Dibromopenicillanate S,S-Dioxide；methyl 6,6-dibromopenicillanate 1,1-dioxide；6,6-dibromo-1,1-dioxo-1λ⁶-penicillanic acid methyl ester；6,6-dibromopenicillanic acid methyl ester 1,1 dioxide；methyl 6,6-dibromo-1,1-dioxopenicillanate；methyl (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate；methyl (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 61657-19-0
• 化学式: C₉H₁₁Br₂NO₅S
• 分子量: 405.064
• InChiKey: FVRPVVPIFMHHQD-MHTLYPKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,6-Dibromopenicillanic acid 1,1-dioxide methyl ester 在 silver nitrate 作用下， 以 异丙醇 为溶剂， 以83%的产率得到methyl (2S,5R,6R)-6-bromo-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  Stereoselective Preparation of 6-b-Bromopenicillanic Acid Derivatives

  摘要：

  A new stereoselective method for the preparation of 6-beta-bromopenicillanates is described. It comprises the reaction of 6,6-dibromopenicillanates with silver nitrate in 2-propanol.

  DOI：

  10.3987/com-94-6898
• 作为产物：
  描述：

  6,6-二溴青霉烷酸 在 potassium permanganate 、 碳酸氢钠 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 6,6-Dibromopenicillanic acid 1,1-dioxide methyl ester
  参考文献：
  名称：

  Studies on 6-halo- and 6,6-dihalopenicillins: the rearrangement of methyl 6,6-dibromopenicillanate to 1,4-thiazepine

  摘要：

  DOI：

  10.1021/jo00356a020

文献信息

• 2-Oxoazetidines, methods for their preparation, and their use
  申请人：Sanraku Incorporation

  公开号：US04855421A1

  公开（公告）日：1989-08-08

  The invention relates to new 2-oxoazetidines having the formulas ##STR1## where R.sub.1 stands for a lower fluoroalkyl or an optionally protected lower hydroxyalkyl group; R.sub.2 for chlorine, bromine, iodine, fluorine, an ##STR2## group in which n is 0, 1 or 2 and R.sub.5 is a lower alkyl, lower alkenyl, an optionally substituted benzyl group, optionally substituted phenyl group, a --CH.sub.2 COX group in which X means a lower alkyl, lower alkoxy or the amino group, or a ##STR3## group in which Y and Z are the same or different and in each case stand for oxygen, nitrogen or sulphur and R.sub.6 stands for a lower alkyl, lower alkoxy, lower alkylthio, lower dialkylamino, an aryl, aryloxy or arylthio group, or for a group having the formula ##STR4## where W stands for --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or C.sub.6 H.sub.4 ; R.sub.3 stands for bromine, chlorine, iodine, SeC.sub.6 H.sub.5 or SC.sub.6 H.sub.5 ; and R.sub.4 stands for hydrogen, a group having the formula ##STR5## in which R.sub.7 is a lower alkyl, an optionally substituted benzyl or an optionally substituted benzohydryl group; or they represent a protecting group, with the proviso that in compounds of formula Ia R.sub.2 does not stand for SCH.sub.3 when R.sub.1 means hydroxyethyl, R.sub.3 means bromine and R.sub.4 means the group of formula IIa, as well as to methods for their preparation and to their use.

  本发明涉及具有以下式子的新型2-氧代吡嗪：##STR1##其中，R.sub.1代表较低的氟代烷基或可选的保护较低的羟基烷基；R.sub.2代表氯、溴、碘、氟、##STR2##其中n为0、1或2，R.sub.5为较低的烷基、较低的烯基、可选地取代的苄基、可选地取代的苯基、--CH.sub.2 COX基，其中X表示较低的烷基、较低的烷氧基或氨基，或者##STR3##其中Y和Z相同或不同，分别代表氧、氮或硫，R.sub.6代表较低的烷基、较低的烷氧基、较低的烷硫基、较低的二烷基氨基、芳基、芳氧基或芳硫基，或者代表具有以下式子的基团##STR4##其中W代表--CH.sub.2 CH.sub.2 --、--CH.dbd.CH--或C.sub.6 H.sub.4；R.sub.3代表溴、氯、碘、SeC.sub.6 H.sub.5或SC.sub.6 H.sub.5；R.sub.4代表氢、具有以下式子的基团##STR5##其中R.sub.7为较低的烷基、可选地取代的苄基或可选地取代的苯甲酰基基团；或它们代表保护基，但有条件地，在式Ia的化合物中，当R.sub.1代表羟乙基，R.sub.3代表溴，R.sub.4代表式IIa的基团时，R.sub.2不代表SCH.sub.3。本发明还涉及其制备方法和用途。
• Procedure for the preparation of dioxopenicillanic acid derivatives
  申请人：ASTUR PHARMA S.A.

  公开号：EP1041075B1

  公开（公告）日：2005-02-02
• Practical synthesis of (3S,4R)-3-[(R)-1-(tert-butyldimethylsiloxy)-ethyl]-4-(methylsulfonyl)-2-azetidinone from dibromopenicillanic acid S,S-dioxide: a penem synthon
  作者：George J. Quallich、Jon Bordner、Mark L. Elliott、Peter Morrissey、Robert A. Volkmann、Magdalena M. Wroblewska-Adams

  DOI：10.1021/jo00288a069

  日期：1990.1
• Stereoselectivity in 6-halopenicillanate grignard reactions
  作者：Bradley B. Brown、Robert A. Volkmann

  DOI：10.1016/s0040-4039(00)84308-7

  日期：1986.1
• TRANSFORMATION OF 6-HALOPENICILLANATES INTO 3-HALO-4-OXOAZETIDINE DERIVATIVES
  作者：Irena Lukić

  DOI：10.1080/00304949909458334

  日期：1999.6