6-Bromo-2-methoxymethyl-9-fluorenone Dimethyl Ketal | 157702-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 6-Bromo-2-methoxymethyl-9-fluorenone Dimethyl Ketal
• 英文别名: 6-Bromo-9,9-dimethoxy-2-(methoxymethyl)fluorene
• CAS: 157702-63-1
• 化学式: C₁₇H₁₇BrO₃
• 分子量: 349.224
• InChiKey: BECMFSHLOWKIMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Bromo-2-methoxymethyl-9-fluorenone Dimethyl Ketal 在 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.5h， 生成 [4S-(4α,5β,6β(S*))]-1-(2-amino-2-oxoethyl)-({6-[4-methyl-2-({[(4-nitrophenyl)methyl]oxy}carbonyl)-7-oxo-6-(1-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)-1-azabicyclo[3.2.0]hept-2-en-3-yl]-9-oxo-9H-fluoren-2-yl}methyl)-1,4-diazaniabicyclo[2.2.2]o...
  参考文献：
  名称：

  Practical Synthesis of Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Carbapenem L-742,728

  摘要：

  Ani-MRSA carbapenem, L-742,728, has been prepared in large quantity using, the Suzuki-Miyaura cross-coupling as the key reaction. Three approaches have been examined by varying the coupling reaction between carbapenem nucleus A and side chains B, BC, and BCD, wherein BCD represents the fully elaborated side chain. The coupling of A with BCD offers the advantage of convergence and requires fewer chemical steps after installation of the thermally unstable carbapenem skeleton. This key reaction highlights the versatility and efficiency of the Suzuki-Miyaura reaction. This approach offers a general method for the preparation of the 3-aryl carbapenems, which possess strong antibacterial activity against resistant strains.

  DOI：

  10.1021/jo980381n
• 作为产物：
  描述：

  3-bromo-7-methyl-9-fluorenone 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异庚腈 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 37.5h， 生成 6-Bromo-2-methoxymethyl-9-fluorenone Dimethyl Ketal
  参考文献：
  名称：

  Practical Synthesis of Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Carbapenem L-742,728

  摘要：

  Ani-MRSA carbapenem, L-742,728, has been prepared in large quantity using, the Suzuki-Miyaura cross-coupling as the key reaction. Three approaches have been examined by varying the coupling reaction between carbapenem nucleus A and side chains B, BC, and BCD, wherein BCD represents the fully elaborated side chain. The coupling of A with BCD offers the advantage of convergence and requires fewer chemical steps after installation of the thermally unstable carbapenem skeleton. This key reaction highlights the versatility and efficiency of the Suzuki-Miyaura reaction. This approach offers a general method for the preparation of the 3-aryl carbapenems, which possess strong antibacterial activity against resistant strains.

  DOI：

  10.1021/jo980381n

文献信息

• Boron containing intermediates useful in the preparation of carbapenems
  申请人：Merck & Co., Inc.

  公开号：US05338875A1

  公开（公告）日：1994-08-16

  The present invention is directed to intermediates of the following formula which are useful in the preparation of Carbapenem-antibiotics ##STR1##

  本发明涉及以下式的中间体，其在制备碳青霉烯类抗生素方面有用：##STR1##
• [EN] 1- beta -METHYL-CARBAPENEM, COMPOSITIONS CONTAINING SAME AND METHODS OF USE<br/>[FR] 1- beta -METHYLE-CARBAPENEM, COMPOSITIONS CONTENANT CE COMPOSE ET SES PROCEDES D'UTILISATION
  申请人：MERCK & CO., INC.

  公开号：WO1995021841A1

  公开（公告）日：1995-08-17

  (EN) A carbapenem antibiotic of formula (I) is disclosed. The variable (a) represents a counterion. Pharmaceutical compositions and methods of use are also disclosed.(FR) L'invention se rapporte à un antibiotique à base de carbapenem de la formule (I). La variable (a) représente un contre-ion. L'invention se rapporte également aux compositions pharmaceutiques et aux procédés d'utilisation de ce composé.

  一种化学式为(I)的碳青霉烯类抗生素被揭示。变量(a)代表一个反离子。还揭示了药物组成和使用方法。
• US5451579A
  申请人：——

  公开号：US5451579A

  公开（公告）日：1995-09-19
• [EN] 2-(FLUORENONYL)-CARBAPENEMS, COMPOSITIONS AND METHODS OF USE<br/>[FR] 2-(FLUORENONYL)-CARBAPENEMS, COMPOSITIONS ET PROCEDES D'UTILISATION
  申请人：MERCK & CO., INC.

  公开号：WO1997004770A1

  公开（公告）日：1997-02-13

  (EN) Carbapenems are disclosed in which the 2-position sidechain contains a fluorenone moiety that is substituted by a bis cationic group. The compounds are of general formula (I). The compounds are effective for treating methicillin resistant staphylococcus aureus (MRSA) and methicillin resistant coagulase negative staphylococcus (MRCNS). Pharmaceutical compositions and methods of treatment are also included.(FR) Cette invention concerne des carbapenems dans lesquels la chaîne latérale en position 2 contient une fraction fluorénone qui est substituée par un groupe bis cationique. Les composés sont représentés par la formule générale (I). Ces composés sont utiles pour traiter le staphylocoque doré résistant à la méthicilline et le staphylocoque négatif à la coagulase résistant à la méthicilline. Des compositions pharmaceutiques et des procédés de traitement sont également présentés.
• Practical Synthesis of Anti-Methicillin-Resistant <i>Staphylococcus</i> <i>Aureus</i> (MRSA) Carbapenem L-742,728
  作者：Nobuyoshi Yasuda、Mark A. Huffman、Guo-Jie Ho、Lyndon C. Xavier、Chunhua Yang、Khateeta M. Emerson、Fuh-Rong Tsay、Yulan Li、Michael H. Kress、Dale L. Rieger、Sandor Karady、Paul Sohar、Newton L. Abramson、Ann E. DeCamp、David J. Mathre、Alan W. Douglas、Ulf-H. Dolling、Edward J. J. Grabowski、Paul J. Reider

  DOI：10.1021/jo980381n

  日期：1998.8.1

  Ani-MRSA carbapenem, L-742,728, has been prepared in large quantity using, the Suzuki-Miyaura cross-coupling as the key reaction. Three approaches have been examined by varying the coupling reaction between carbapenem nucleus A and side chains B, BC, and BCD, wherein BCD represents the fully elaborated side chain. The coupling of A with BCD offers the advantage of convergence and requires fewer chemical steps after installation of the thermally unstable carbapenem skeleton. This key reaction highlights the versatility and efficiency of the Suzuki-Miyaura reaction. This approach offers a general method for the preparation of the 3-aryl carbapenems, which possess strong antibacterial activity against resistant strains.