(4S,5R,6S(R))-3-(hydroxymethyl)-4-methyl-6-<1-<<(2-propenoxy)carbonyl>oxy>ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-enecarboxylic acid 2-propenyl ester | 118990-99-1

• 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: (4S,5R,6S(R))-3-(hydroxymethyl)-4-methyl-6-<1-<<(2-propenoxy)carbonyl>oxy>ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-enecarboxylic acid 2-propenyl ester
• 英文别名: allyl (1S,5R,6S)-6-[(1R)-1-(allyloxycarbonyloxy)ethyl]-2-hydroxymethyl-1-methyl-1-carbapen-2-em-3-carboxylate；allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-(allyloxycarbonyl)oxyethyl]-1-methylcarbapen-2-em-3-carboxylate；allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylate；allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-2-hydroxymethyl-1-methyl-carbapen-2-em-3-carboxylate；(4S,5R,6S(R))-3-(hydroxymethyl)-4-methyl-6-(1-{[(2-propenoxy)carbonyl]oxy}ethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-enecarboxylic acid 2-propenyl ester；prop-2-enyl (4S,5R,6S)-3-(hydroxymethyl)-4-methyl-7-oxo-6-[(1R)-1-prop-2-enoxycarbonyloxyethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 118990-99-1
• 化学式: C₁₈H₂₃NO₇
• 分子量: 365.383
• InChiKey: XXHRZPCLDXMDGU-OIMNJJJWSA-N

物化性质

• 沸点：
  527.4±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S(R))-3-(hydroxymethyl)-4-methyl-6-<1-<<(2-propenoxy)carbonyl>oxy>ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-enecarboxylic acid 2-propenyl ester 在 四(三苯基膦)钯 、 2-乙基-己酸稀土盐 、 potassium 2-ethylhexanoate 、 三苯基膦 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.0h， 以76%的产率得到<4S,5R,6S(R)>-6-(1-hydroxyethyl)-3-(hydroxymethyl)-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid potassium salt
  参考文献：
  名称：

  Dual-action penems and carbapenems

  摘要：

  Two new series of dual-action antibacterial agents were synthesized in which penems and carbapenems were linked at the 2'-position to quinolones through either an ester or a carbamate moiety. Potent, broad-spectrum antibacterial activity was observed for both classes of compounds, indicative of a dual-mode of action.

  DOI：

  10.1021/jm00088a019
• 作为产物：
  描述：

  prop-2-enyl 2-[(2R,3S)-2-[(2R)-4-hydroxy-3-oxobutan-2-yl]-4-oxo-3-[(1R)-1-prop-2-enoxycarbonyloxyethyl]azetidin-1-yl]-2-(triphenyl-lambda5-phosphanylidene)acetate 以76%的产率得到
  参考文献：
  名称：

  SCHMITT, SUSAN M.;SALZMANN, THOMAS N.;SHIH, DAVID H.;CHRISTENSEN, BURTON +, J. ANTIBIOTICS, 41,(1988) N 6, 780-787

  摘要：

  DOI：

文献信息

• Carbapenem antibacterial compounds, compositions containing such compounds and methods of treatment
  申请人：Merck & Co., Inc.

  公开号：US06346526B1

  公开（公告）日：2002-02-12

  Compounds of formula I: as well as pharmaceutically acceptable salts thereof useful as carbapenem antibacterial agents are disclosed wherein X is CH2 or C═O.

  公开了式I的化合物及其药学上可接受的盐，其作为碳青霉烯类抗菌剂有用，其中X为CH2或C═O。
• Carbapenem antibacterial compounds, compositions containing such compounds and method of treatment
  申请人：Merck & Co., Inc.

  公开号：US06294528B1

  公开（公告）日：2001-09-25

  Compounds of formula I: as well as pharmaceutically acceptable salts therefor and compositions useful as carbapenem antibacterial agents are disclosed.

  本发明公开了化学式I的化合物，以及其药学上可接受的盐和用作碳青霉烯抗菌剂的组合物。
• Crystalline carbapenem intermediate
  申请人：Aihara Kazuhiro

  公开号：US20070167620A1

  公开（公告）日：2007-07-19

  This invention relates to crystals of compounds of formula (I), wherein TBS represents t-butyldimethylsilyl, and Ph represents phenyl, or its salt or solvate. Compounds of formula (I) are synthesis intermediates of 2-substituted-1β-methyl carbapenem compounds useful as antimicrobial agents. The crystals of the present invention have excellent handleability and can realize the production of carbapenem compounds having excellent antimicrobial actibity in a simpler manner with improved yield and purity.

  本发明涉及式（I）化合物的晶体，其中TBS代表叔丁基二甲基硅基，Ph代表苯基，或其盐或溶剂合物。式（I）化合物是2-取代-1β-甲基头孢烯类化合物的合成中间体，可用作抗微生物剂。本发明的晶体具有优异的可操作性，可以更简单地实现生产具有优异抗微生物活性的头孢烯类化合物，同时提高产率和纯度。
• Carbapenem derivatives
  申请人：Meiji Seika Kabushiki Kaisha

  公开号：US05990101A1

  公开（公告）日：1999-11-23

  Novel carbapenem derivatives, represented by the following formula (I), having a substituted or unsubstituted imidazo[5,1-b]thiazolium-6-ylmethyl group at the 2-position are disclosed. The compounds represented by the formula (I) have potent antibacterial activity against a wide spectrum of bacteria from Gram-positive bacteria to Gram-negative bacteria including Pseudomonas aeruginosa and, in addition, have potent antibacterial activity against various .beta.-lactamase-producing bacteria and MRSA and are very stable against DHP-1. ##STR1##

  本发明揭示了一种具有以下式(I)的取代或未取代的咪唑[5,1-b]噻唑-6-基甲基基团的新型碳青霉烯衍生物。公式（I）代表的化合物对从革兰氏阳性菌到革兰氏阴性菌包括铜绿假单胞菌在内的广谱细菌具有强效的抗菌活性，此外，它们对各种β-内酰胺酶产生的细菌和MRSA具有强效的抗菌活性，并且对DHP-1非常稳定。 ##STR1##
• NOVEL CARBAPENEM DERIVATIVES
  申请人：MEIJI SEIKA KABUSHIKI KAISHA

  公开号：EP0760370A1

  公开（公告）日：1997-03-05

  Novel carbapenem derivatives, represented by the following formula (I), having a substituted or unsubstituted imidazo[5,1-b]thiazolium-6-ylmethyl group at the 2-position are disclosed. The compounds represented by the formula (I) have potent antibacterial activity against a wide spectrum of bacteria from Gram-positive bacteria to Gram-negative bacteria including Pseudomonas aeruginosa and, in addition, have potent antibacterial activity against various β-lactamase-producing bacteria and MRSA and are very stable against DHP-1.

  本发明公开了由下式(I)表示的新型碳青霉烯类衍生物，其 2-位具有取代或未取代的咪唑并[5,1-b]噻唑鎓-6-基甲基。由式（I）代表的化合物对从革兰氏阳性菌到革兰氏阴性菌（包括铜绿假单胞菌）在内的广谱细菌具有强效抗菌活性，此外，还对各种产β-内酰胺酶细菌和 MRSA 具有强效抗菌活性，并且对 DHP-1 非常稳定。