Diphenylmethyl (7S,6R)-7-(phenoxyacetamido)-3-ethyl-3-cephem-4-carboxylate | 130516-10-8

• 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: Diphenylmethyl (7S,6R)-7-(phenoxyacetamido)-3-ethyl-3-cephem-4-carboxylate
• 英文别名: diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-ethylceph-3-em-4-carboxylate；benzhydryl (6R,7R)-3-ethyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 130516-10-8
• 化学式: C₃₀H₂₈N₂O₅S
• 分子量: 528.629
• InChiKey: HCGDAOJKMLSEID-VAVYLYDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  diphenylmethyl 3-hydroxy-2-<(3R,4R)-2-oxo-3-(phenoxyacetylamino)-4-(p-tolylsulfonylthio)-1-azetidinyl>-2-butenoate 在 copper(l) iodide 、 TEA 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.58h， 生成 Diphenylmethyl (7S,6R)-7-(phenoxyacetamido)-3-ethyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  A Novel Approach to Cephalosporins From Allenylazetidinones: A New Cyclization Strategy via Tandem Cuprate Addition-Sulfenylation

  摘要：

  An efficient approach to the synthesis of 3-substituted cephems bearing carbon-based substituents of choice at the C(3) position from inexpensive penicillins is described. The strategy involves the synthesis of an allenylazetidinone from penicillin sulfoxide followed by the addition of an organocuprate at low temperature. Organocuprates undergo 1,4-conjugate addition at the central allenic carbon of the allenylazetidinone to form a carbon-carbon bond which is followed by ring closure via an intramolecular sulfenylation reaction. The chemistry has been applied to the synthesis of a variety of 3-substituted cephems bearing substituents such as alkyl, cycloalkyl, aryl, alkenyl, and allyl. Precursors to the synthesis of important antibiotics, i.e., Cefadroxil, Cefixime, and Cefzil, are also available from this novel approach. The methodology is not limited to carbon-based 3-substituted cephems, but provides access to some 3-norcephalosporins as well.

  DOI：

  10.1021/jo00096a045

文献信息

• Nucleophilic substitution of 3-fluorosulfonyloxy cephalosporins with organocuprates
  作者：Gregory P. Roth、Scott A. Peterson、Joydeep Kant

  DOI：10.1016/s0040-4039(00)79294-x

  日期：1993.11

  3-Fluorosulfonyloxy cephems readily undergo addition-elimination reactions with organocuprates derived from the corresponding Grignard reagents. This chemistry presents an efficient, cost effective process for the preparation of 3-substituted cephems.

  3-氟磺酰氧基头孢烷容易与衍生自相应格氏试剂的有机铜酸盐进行加成消除反应。这种化学方法提供了一种高效，经济的方法来制备3-取代的头孢烯。
• Reactions of organocuprates with vinyl-triflates and related cephems: A novel approach to 3-substituted cephalosporins
  作者：Joydeep Kant、Chester Sapino、Stephen R. Baker

  DOI：10.1016/s0040-4039(00)97404-5

  日期：1990.1

  Vinyl-triflates and related 3-substituted cephems readily undergo addition-elimination reactions with a variety of organocuprates to form new carbon-carbon bonds. This chemistry presents a novel approach to the synthesis of 3-alkyl, 3-aryl, and 3-alkenylcephalosporins.

  乙烯基三氟甲磺酸酯和相关的3-取代的头孢很容易与各种有机铜化合物进行加成消除反应，以形成新的碳-碳键。该化学方法提供了一种合成3-烷基，3-芳基和3-烯基头孢菌素的新颖方法。
• A synthetic approach to 3-substituted cephalosporins: carbon-carbon bond formation at C(3) of the cephem via organocuprate chemistry
  作者：Joydeep Kant

  DOI：10.1021/jo00060a054

  日期：1993.4

  An efficient approach to the synthesis of 3-substituted cephalosporins is described. 3-Trifloxycephems readily undergo addition-elimination reactions with a variety of organocuprates to form carbon-carbon bonds at the C(3) position of the cephem nucleus. The organocuprates derived from Grignard reagents and copper(I) bromide-dimethyl sulfide complex in THF functioned most effectively in the reaction and did not promote any concurrent DELTA3/DELTA2 isomerization (a problem commonly encountered in cephalosporin chemistry). The chemistry was applied to the synthesis of a variety of 3-substituted cephalosporins bearing carbon substituents including alkyl, cycloalkyl, aryl, alkenyl, and allyl. Precursors for the synthesis of the antibiotics Cefadroxil, Cefixime, and Cefzil are also available via this route.
• KANT, JOYDEEP;SAPINO, CHESTER (JR);BAKER, STEPHEN R., TETRAHEDRON LETT., 31,(1990) N4, C. 3389-3392
  作者：KANT, JOYDEEP、SAPINO, CHESTER (JR)、BAKER, STEPHEN R.

  DOI：——

  日期：——
• A Novel Approach to Cephalosporins From Allenylazetidinones: A New Cyclization Strategy via Tandem Cuprate Addition-Sulfenylation
  作者：Joydeep Kant、Jeanine A. Roth、Carl E. Fuller、Donald G. Walker、Daniel A. Benigni、Vittorio Farina

  DOI：10.1021/jo00096a045

  日期：1994.8

  An efficient approach to the synthesis of 3-substituted cephems bearing carbon-based substituents of choice at the C(3) position from inexpensive penicillins is described. The strategy involves the synthesis of an allenylazetidinone from penicillin sulfoxide followed by the addition of an organocuprate at low temperature. Organocuprates undergo 1,4-conjugate addition at the central allenic carbon of the allenylazetidinone to form a carbon-carbon bond which is followed by ring closure via an intramolecular sulfenylation reaction. The chemistry has been applied to the synthesis of a variety of 3-substituted cephems bearing substituents such as alkyl, cycloalkyl, aryl, alkenyl, and allyl. Precursors to the synthesis of important antibiotics, i.e., Cefadroxil, Cefixime, and Cefzil, are also available from this novel approach. The methodology is not limited to carbon-based 3-substituted cephems, but provides access to some 3-norcephalosporins as well.