p-nitrobenzyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo [3,2,0]hept-2-en-6-yl]-α-(1-hydroxyethylidene)acetate | 61875-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-nitrobenzyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo [3,2,0]hept-2-en-6-yl]-α-(1-hydroxyethylidene)acetate
• 英文别名: p-Nitrobenzyl alpha-[3-phenoxymethyl-7-oxo4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(1-hydroxyethylidene)acetate；(4-nitrophenyl)methyl 3-hydroxy-2-[7-oxo-3-(phenoxymethyl)-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]but-2-enoate
• CAS: 61875-03-4
• 化学式: C₂₂H₁₉N₃O₇S
• 分子量: 469.475
• InChiKey: JPYXUNNVYFMVJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo [3,2,0]hept-2-en-6-yl]-α-(1-hydroxyethylidene)acetate 、 二苯基次膦酰氯 在 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 diphenyl 1-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-1-(p-nitrobenzyloxycarbonyl)-prop-1-en-2-yl phosphate
  参考文献：
  名称：

  Preparation of 3-substituted cephalosporins

  摘要：

  描述了一种制备式（IX）的烯胺的过程：其中R.sup.2是羧酸保护基，R.sup.3是羧酸衍生酰基的残基，R.sup.5和R.sup.6是相同或不同的C.sub.1-4烷基或C.sub.7-10芳基烷基；或者与相邻的氮原子一起形成含有4至8个碳原子和可选地从氧和氮中选择的进一步杂原子的杂环环的异构体；通过将式（XII）的化合物与式HNR.sup.5 R.sup.6的胺反应，其中式（XII）的反应物是通过将适当的烯醇衍生物与磷试剂反应制备的。式（IX）的烯胺在3-羟基头孢菌素的制备中很有用。

  公开号：

  US04301280A1

文献信息

• Cyclization to form cephem ring and intermediates therefor
  申请人：Shionogi & Co., Ltd.

  公开号：US04160085A1

  公开（公告）日：1979-07-03

  Intermediates represented by the following formulas are useful for synthesizing 3-hydroxy-3-cephem compounds ##STR1## wherein A and B each is a hydrogen or amino substituent; R is a hydrogen or thiol substituent; Hal is a halogen; X is a hydroxy or carboxy protecting group; the broken line between A and R shows that when R and B are hydrogens, and A is a carboxylic acyl, the substituents can be combined to form an azetidinothiazoline bicyclic ring; and the enamine derivatives thereof. One embodiment provides for cyclizing a compound of the formula: ##STR2## wherein A, B, X and Hal are as defined above, which comprises treating the said compound with an acid, base, or solvent if required in the presence of a catalyzer to give a compound represented by following formula ##STR3## In a further embodiment a compound represented by the following formula ##STR4## wherein A, B, R and X are as defined above, is prepared by a process which comprises treating an enamine of a compound represented by following formula ##STR5## wherein A, B, R, X, Hal and broken line are as defined above, with a disubstituted amino containing from 2 to 20 carbon atoms, with the action of an aqueous acid.

  以下式子代表的中间体在合成3-羟基-3-头孢烷化合物时非常有用：##STR1## 其中A和B均为氢或氨基取代基；R为氢或硫醇取代基；Hal为卤素；X为羟基或羧基保护基；A和R之间的断裂线表示当R和B为氢，A为羧酸酰基时，取代基可以结合形成氮杂环硫唑双环环；以及其烯胺衍生物。一种实施例提供了将以下式子的化合物环化：##STR2## 其中A、B、X和Hal如上所定义，包括在催化剂存在下，用酸、碱或必要的溶剂处理所述化合物，以给出以下式子所代表的化合物：##STR3## 在另一种实施例中，通过将以下式子所代表的烯胺与含有2至20个碳原子的二取代氨基化合物在水酸的作用下处理，制备出以下式子所代表的化合物：##STR4## 其中A、B、R和X如上所定义。
• Cyclization to form cephem ring and azetidinone intermediates therefor
  申请人：Shionogi & Co., Ltd.

  公开号：US04440683A1

  公开（公告）日：1984-04-03

  An intermediate represented by following formula for synthesizing 3-hydroxy-3-cephem compounds. ##STR1## wherein A and B each is a hydrogen or amine substituent; R is a hydrogen or thiol substituent; Nal is a halogen; X is a hydroxy or carboxy protecting group; the broken line between A and R shows that when R and B are hydrogens, and A is a carboxylic acyl, the substituents can be combined to form an azetidimethiazoline bicyclic ring; and the enamine derivatives thereof.

  以下公式代表合成3-羟基-3-头孢菌素类化合物的中间体。其中A和B分别为氢或胺基取代基；R为氢或硫醇取代基；Nal为卤素；X为羟基或羧基保护基；A和R之间的断线表示当R和B为氢，A为羧酸酰基时，取代基可以组合形成一种氮杂环庚烷-噻唑啉二环环。以及其烯胺衍生物。
• Certain 7-oxo-4-thio-2,6-diazabicyclo-3,2,0-hept-2-ene compounds
  申请人：Shionogi & Co., Ltd.

  公开号：US04079181A1

  公开（公告）日：1978-03-14

  An intermediate represented by following formula for synthesizing 3-hydroxy-3-cephem compounds. ##STR1## wherein A and B each is a hydrogen or amino substituent; R is a hydrogen or thiol substituent; Hal is a halogen; X is a hydroxy or carboxy protecting group; the broken line between A and R shows that when R and B are hydrogens, and A is a carboxylic acyl, the substituents can be combined to form an azetidinothiazoline bicyclic ring; and the enamine derivatives thereof.

  以下是用于合成3-羟基-3-头孢菌素化合物的中间体，其表示为以下公式：##STR1## 其中A和B均为氢或氨基取代基；R为氢或硫醇取代基；Hal为卤素；X为羟基或羧基保护基；A和R之间的断线表示当R和B为氢，A为羧酸酰基时，取代基可以结合形成氮杂环己硫噻唑双环环；以及其烯胺衍生物。
• Cyclization process to form cephem ring
  申请人：Shionogi & Co., Ltd.

  公开号：US04346218A1

  公开（公告）日：1982-08-24

  An intermediate represented by following formula for synthesizing 3-hydroxy-3-cephem compounds ##STR1## wherein A and B each is a hydrogen or amino substituent; R is a hydrogen or thiol substituent; Hal is a halogen; X is a hydroxy or carboxy protecting group; the broken line between A and R shows that when R and B are hydrogens, and A is a carboxylic acyl, the substituents can be combined to form an azetidinothiazoline bicyclic ring; and the enamine derivatives thereof.

  以下公式代表合成3-羟基-3-头孢烷化合物的中间体：##STR1## 其中，A和B分别是氢或氨基取代基；R是氢或硫醇取代基；Hal是卤素；X是羟基或羧基保护基；A和R之间的断裂线表示当R和B为氢，A为羧酸酰基时，取代基可以结合形成氮杂环硫杂环双环；以及其烯胺衍生物。
• Preparation of 3-substituted cephalosporins
  申请人：Lilly Industries Limited

  公开号：US04301280A1

  公开（公告）日：1981-11-17

  There is described a process for preparing an enamine of formula (IX): ##STR1## where R.sup.2 is a carboxylic acid protecting group and R.sup.3 is the residue of a carboxylic acid derived acyl group and where R.sup.5 and R.sup.6 are the same or different C.sub.1-4 alkyl or C.sub.7-10 aralkyl groups; or taken together with the adjacent nitrogen atom form a heterocyclic ring containing from 4 to 8 carbon atoms and optionally a further heteroatom selected from oxygen and nitrogen; by reacting a compound of formula (XII): ##STR2## with an amine of formula HNR.sup.5 R.sup.6, the reactant of formula (XII) being prepared by reaction of an appropriate enol derivative with a phosphorus reagent. The enamines of formula (IX) are useful in the preparation of 3-hydroxycephalosporins.

  描述了一种制备式（IX）的烯胺的过程：其中R.sup.2是羧酸保护基，R.sup.3是羧酸衍生酰基的残基，R.sup.5和R.sup.6是相同或不同的C.sub.1-4烷基或C.sub.7-10芳基烷基；或者与相邻的氮原子一起形成含有4至8个碳原子和可选地从氧和氮中选择的进一步杂原子的杂环环的异构体；通过将式（XII）的化合物与式HNR.sup.5 R.sup.6的胺反应，其中式（XII）的反应物是通过将适当的烯醇衍生物与磷试剂反应制备的。式（IX）的烯胺在3-羟基头孢菌素的制备中很有用。