(1S,3S,5R,6R) 2,2-Dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide diphenylmethyl ester | 37591-67-6

• 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: (1S,3S,5R,6R) 2,2-Dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide diphenylmethyl ester
• 英文别名: Benzhydryl penicillin V sulfoxide, (S)-；benzhydryl (2S,4S,5R,6R)-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4λ4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 37591-67-6
• 化学式: C₂₉H₂₈N₂O₆S
• 分子量: 532.617
• InChiKey: LCRVLXSXMGVJHV-RNSLDFKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,3S,5R,6R) 2,2-Dimethyl-6-phenoxyacetamidopenam-3-carboxylic acid-1-oxide diphenylmethyl ester 以 1,4-二氧六环 、 二苯基甲基(6R-反式)-3-甲基-8-氧代-7-(苯氧基乙酰氨基)-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸酯 、 丙酮 为溶剂， 生成 二苯基甲基(6R-反式)-3-甲基-8-氧代-7-(苯氧基乙酰氨基)-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸酯
  参考文献：
  名称：

  Process for producing carbamoyl substituted penams and carbamoyl

  摘要：

  盼西林亚砜酯与异氰酸酯反应，生成相应的（取代）-2-氨基羧甲基青霉素，相应的（取代）-3-氨基羧甲氧头孢菌素或相应的3-甲基头孢菌素。这些产物的6-或7-侧链可以被裂解，得到相应的6-氨基（青霉素）或7-氨基（头孢菌素和头孢菌素）化合物，后者可以重新酰化，产生不同的6-酰基-2-氨基羧甲基青霉素，7-酰基-3-氨基羧甲氧头孢菌素和7-酰基-3-甲基头孢菌素。这些取代基团可以从（取代）-2-氨基羧甲氧青霉素或（取代）-3-氨基羧甲氧头孢菌素中去除，分别得到相应的游离2-氨基羧甲基青霉素或3-氨基羧甲氧头孢菌素。

  公开号：

  US04310459A1

文献信息

• 6-Amino penam derivatives
  申请人：Bristol-Myers Company

  公开号：US04407755A1

  公开（公告）日：1983-10-04

  Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcephem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. The substituent groups may be removed from the (substituted)-2-carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively.

  青霉素亚砜酯与异氰酸酯反应，可产生相应的（取代）-2-氨氧甲基青霉烯，相应的（取代）-3-氨氧甲基头孢菌素或相应的3-甲基头孢菌素。这些产物的6-或7-侧链可以裂解，从而得到相应的6-氨基（青霉烯）或7-氨基（头孢菌素和头孢菌素）化合物，后者可以重新酰化以产生不同的6-酰基-2-氨氧甲基青霉烯，7-酰基-3-氨氧甲基头孢菌素和7-酰基-3-甲基头孢菌素。取代基团可以从（取代）-2-氨氧甲基青霉烯或（取代）-3-氨氧甲基头孢菌素中去除，以得到相应的自由2-氨氧甲基青霉烯或3-氨氧甲基头孢菌素。
• Chemical process
  申请人：Bristol-Myers Company

  公开号：US04176131A1

  公开（公告）日：1979-11-27

  Optionally substituted silicon isocyanates are prepared by reacting a corresponding silicon halide with an alkali metal cyanate or an alkaline earth metal cyanate in an inert solvent having a dielectric constant below about 10, in the presence of a crown ether as a catalyst.

  可选取代硅异氰酸酯是通过在具有介电常数低于约10的惰性溶剂中，在王冠醚存在下，将相应的硅卤化物与碱金属氰酸盐或碱土金属氰酸盐反应制备的。
• 3-Carbamoyloxy-cepham-4-carboxylic acid derivatives
  申请人：Bristol-Myers Company

  公开号：US04426520A1

  公开（公告）日：1984-01-17

  Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcepem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. The substituent groups may be removed from the (substituted)-2-carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively.

  青霉素磺酰氧酯与异氰酸酯反应，得到相应的（取代）-2-氨氧甲基青霉烯、相应的（取代）-3-氨氧甲基头孢菌素或相应的3-甲基头孢烯。这些产物的6-或7-侧链可被裂解，以得到相应的6-氨基（青霉烯）或7-氨基（头孢菌素和头孢烯）化合物，后者可被重新酰化以产生不同的6-酰基-2-氨氧甲基青霉烯、7-酰基-3-氨氧甲基头孢菌素和7-酰基-3-甲基头孢烯。取代基团可以从（取代）-2-氨氧甲基青霉烯或（取代）-3-氨氧甲基头孢菌素中去除，以分别得到相应的自由2-氨氧甲基青霉烯或3-氨氧甲基头孢菌素。
• "3-Carbamoyloxy cephalosporins"
  申请人：Bristol-Myers Company

  公开号：US04518773A1

  公开（公告）日：1985-05-21

  Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcephem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. The substituent groups may be removed from the (substituted)-2-carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively.

  青霉素亚砜酯与异氰酸酯反应，生成相应的（取代）-2-氨氧甲基青霉烯，相应的（取代）-3-氨氧甲基头孢菌素或相应的3-甲基头孢菌素。这些产物的6-或7-侧链可被裂解，以得到相应的6-氨基（青霉烯）或7-氨基（头孢菌素和头孢菌素）化合物，后者可重新酰化以产生不同的6-酰基-2-氨氧甲基青霉烯，7-酰基-3-氨氧甲基头孢菌素和7-酰基-3-甲基头孢菌素。取代基可以从（取代）-2-氨氧甲基青霉烯或（取代）-3-氨氧甲基头孢菌素中除去，以分别得到相应的自由2-氨氧甲基青霉烯或3-氨氧甲基头孢菌素。
• 2-Carbamoyloxymethyl-penicillin derivatives
  申请人：Bristol-Myers Company

  公开号：US04322347A1

  公开（公告）日：1982-03-30

  Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcephem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. The substituent groups may be removed from the (substituted)-2-carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively.

  青霉素硫氧化物酯与异氰酸酯反应，可以产生相应的（取代）-2-氨氧甲基青霉烯，相应的（取代）-3-氨氧甲基头孢菌素或相应的3-甲基头孢菌素。这些产物的6-或7-侧链可以被裂解，以得到相应的6-氨基（青霉烯）或7-氨基（头孢菌素和头孢菌素）化合物，后者可以重新酰化以产生不同的6-酰基-2-氨氧甲基青霉烯，7-酰基-3-氨氧甲基头孢菌素和7-酰基-3-甲基头孢菌素。取代基可以从（取代）-2-氨氧甲基青霉烯或（取代）-3-氨氧甲基头孢菌素中去除，以分别得到相应的自由2-氨氧甲基青霉烯或3-氨氧甲基头孢菌素。