(2R,3R) 1-(1'-p-nitrobenzyloxycarbonyl-2'-methyl-prop-1'-enyl)-2-[(5'-methyl-isoxazol-3'-yl)aminosulfinyl]-3-phthalimido-4-oxo-azetidine | 153785-08-1

• 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: (2R,3R) 1-(1'-p-nitrobenzyloxycarbonyl-2'-methyl-prop-1'-enyl)-2-[(5'-methyl-isoxazol-3'-yl)aminosulfinyl]-3-phthalimido-4-oxo-azetidine
• 英文别名: (4-nitrophenyl)methyl 2-[(2R,3R)-3-(1,3-dioxoisoindol-2-yl)-2-[(5-methyl-1,2-oxazol-3-yl)sulfinamoyl]-4-oxoazetidin-1-yl]-3-methylbut-2-enoate
• CAS: 153785-08-1
• 化学式: C₂₇H₂₃N₅O₉S
• 分子量: 593.574
• InChiKey: GRAQDJDGNFJUIT-FTOJYCGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  204
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,3R) 1-(1'-p-nitrobenzyloxycarbonyl-2'-methyl-prop-1'-enyl)-2-[(5'-methyl-isoxazol-3'-yl)aminosulfinyl]-3-phthalimido-4-oxo-azetidine 在 palladium on activated charcoal 甲酸 、 氢气 、 双氧水 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、253.31 kPa 条件下， 反应 1.0h， 生成 2-[(6R,7R)-2-Isopropylidene-4-(5-methyl-isoxazol-3-yl)-3,5,5,8-tetraoxo-5λ⁶-thia-1,4-diaza-bicyclo[4.2.0]oct-7-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  New functionalized monocyclic beta-lactams suitable precursors for anhydro 2-azacephams

  摘要：

  The anhydro 2-azacephams 9 were prepared starting from penicillanate sulphoxides 1 via 4-aminosulphinyl-2-oxoazetidines 3 and 4 and 4-aminosulphonyl-2-oxoazetidines 6 and 8. New functionalized monocyclic beta-lactams 5 and 7 were also produced as precursors for other beta-lactam species.

  DOI：

  10.1016/s0040-4020(01)80182-4
• 作为产物：
  描述：

  (R)-2-[(2R,3R)-2-Chlorosulfinyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid 4-nitro-benzyl ester 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 (2R,3R) 1-(1'-p-nitrobenzyloxycarbonyl-2'-methyl-prop-1'-enyl)-2-[(5'-methyl-isoxazol-3'-yl)aminosulfinyl]-3-phthalimido-4-oxo-azetidine
  参考文献：
  名称：

  New functionalized monocyclic beta-lactams suitable precursors for anhydro 2-azacephams

  摘要：

  The anhydro 2-azacephams 9 were prepared starting from penicillanate sulphoxides 1 via 4-aminosulphinyl-2-oxoazetidines 3 and 4 and 4-aminosulphonyl-2-oxoazetidines 6 and 8. New functionalized monocyclic beta-lactams 5 and 7 were also produced as precursors for other beta-lactam species.

  DOI：

  10.1016/s0040-4020(01)80182-4

文献信息

• Amides of 4-oxo-azetidine-2-sulfonic acids and salts thereof, processes
  申请人：PLIVA and PLIVA Handels GmbH

  公开号：US05466686A1

  公开（公告）日：1995-11-14

  The invention relates to the novel 4-oxo-azetidine-2-sulfonic acid amides and their salts of the formula I ##STR1## wherein the radicals have the meanings: R.sup.1 =hydrogen, halogen; R.sup.2 =hydrogen, halogen, NH.sub.2, C.sub.6 H.sub.5 CH.sub.2 CONH, C.sub.6 H.sub.5 OCH.sub.2 CONH, phthalimido, o-MeNHCOC.sub.6 H.sub.4 CONH, isoxazolylcarbonylamino; R.sup.3 =hydrogen, Me.sub.2 C.dbd.C--COOMe, H.sub.2 C.dbd.C(Me)--CH--COOMe, Me.sub.2 C.dbd.C--COOCH.sub.2 C.sub.6 H.sub.5, H.sub.2 C.dbd.C(Me)CH--COOCH.sub.2 C.sub.6 H.sub.4 NO.sub.2 -p, Me.sub.2 C.dbd.C--COOCH.sub.2 C.sub.6 H.sub.4 NO.sub.2 -p, Me.sub.2 C.dbd.C--COOCH.sub.2 C.sub.6 H.sub.4 Me-m, H.sub.2 C.dbd.C(Me)--CH--COOCH.sub.2 C.sub.6 H.sub.4 Me-m, Me.sub.2 C.dbd.C--COOH; R.sup.4 =hydrogen or sodium and R.sup.5 =hydrogen, alkyl, benzyl or heterocycle, i.e. isoxazole or pyrazole etc. The invention also relates to the procedure for the preparation thereof and the use thereof as intermediates in the synthesis of beta-lactam analogs or as active components for the preparations of the drugs for antimicrobial therapy.

  本发明涉及新型的4-氧代-氮杂环丁烷-2-磺酸酰胺及其盐，其化学式为I：##STR1## 其中基团的含义为：R1=氢、卤素；R2=氢、卤素、NH2、C6H5CH2CONH、C6H5OCH2CONH、邻苯二甲酰亚胺、o-MeNHCOC6H4CONH、异噁唑基甲酰胺基；R3=氢、Me2C=CH-COOMe、H2C=C(Me)-CH-COOMe、Me2C=CH-COOCH2C6H5、H2C=C(Me)CH-COOCH2C6H4NO2-p、Me2C=CH-COOCH2C6H4NO2-p、Me2C=CH-COOCH2C6H4Me-m、H2C=C(Me)-CH-COOCH2C6H4Me-m、Me2C=CH-COOH；R4=氢或钠；R5=氢、烷基、苯甲基或杂环，即异噁唑或吡唑等。本发明还涉及其制备方法以及用作β-内酰胺类似物的合成中间体或用于制备抗微生物治疗药物的活性成分。
• US5466686A
  申请人：——

  公开号：US5466686A

  公开（公告）日：1995-11-14