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trans-(3S,4S)-1(R)-(α-methylbenzyl)-3-amino-4-methyl-2-azetidinone | 141040-11-1

中文名称
——
中文别名
——
英文名称
trans-(3S,4S)-1(R)-(α-methylbenzyl)-3-amino-4-methyl-2-azetidinone
英文别名
——
trans-(3S,4S)-1(R)-(α-methylbenzyl)-3-amino-4-methyl-2-azetidinone化学式
CAS
141040-11-1
化学式
C12H16N2O
mdl
——
分子量
204.272
InChiKey
HGMVUOLYYKPMDH-YWVKMMECSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.31
  • 重原子数:
    15.0
  • 可旋转键数:
    2.0
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.42
  • 拓扑面积:
    46.33
  • 氢给体数:
    1.0
  • 氢受体数:
    2.0

反应信息

  • 作为产物:
    参考文献:
    名称:
    Enantioselective synthesis of 3-amino-2-azetidinones via the ester enolate - imine condensation
    摘要:
    Three approaches to the enantioselective synthesis of 3-amino-4-substituted-2-azetidinones by condensation of alpha-amino ester enolates with imines are described: (i) application of chiral ester derivatives of NN-diethylglycine; (ii) application of chiral N-(alpha-methylbenzyl)imines; and (iii) application of chiral imines derived from (2R)-2,3-O-isopropylideneglyceraldehyde. Zinc and aluminum enolates of (-)-menthyl- and (-)-bornyl NN-diethylglycine esters react with simple imines to selectively afford trans-3-(diethylamino)-2-azetidinones, but with a low chiral induction (ee 0-35%). However, reactions of the metal (Li, Zn, Al) ester enolates of (2,2,5,5-tetramethyl-1-aza-2,4-disilacyclopent-1-yl)acetic acid ethyl ester (1c) with N-(alpha-methylbenzyl)imines yield N-protected 3-amino-2-azetidinones in excellent yields and with very high diastereo- and enantioselectivities. The best results are obtained for the zinc-mediated reactions. For example, trans-(3R,4S)-1(R)-(alpha-methylbenzyl)-3-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)-4-[N-(R)-(alpha-methylbenzyl)imino]-2-azeti dineone (4a), a fully protected key intermediate (having the unnatural C-3 configuration) for the synthesis of known monobactam and bicyclic beta-lactam antibiotics, was synthesized in 91% yield with an ee of 91%. Application of chiral imines derived from acetaldehyde and propionaldehyde enable, depending on the solvent, the selective high yielding synthesis (de 60-99%; ee >95%) of any one of the four stereoisomers of 3-amino-4-alkyl-2-azetidinones, which are key intermediates for the synthesis of Aztreonam and related antibiotics. In Et2O, a weakly polar solvent, the trans isomers are formed, whereas the use of a polar THF/HMPA solvent mixture results in formation of the cis isomers. Reaction of the zinc enolate of 1c with the N-(4-methoxyphenyl)imine derivative 2i of (2R)-2,3-O-isopropylidene glyceraldehyde affords trans-(3R,4S)-3-amino-4-[(1'S)-1',2'-O-isopropylideneethyl]-2-azetidinone (10a) in excellent yield (de 86%; ee >98%), whereas reaction of the lithium enolate of 1c with the N-(trimethylsilyl)imine derivative 21 affords the cis-(3S,4S) isomer 10d (key intermediate for the synthesis of Carumonam) in good yield (de >90%; >90%). A rationale for the observed stereoselectivities in terms of highly ordered transition states is presented.
    DOI:
    10.1021/jo00040a034
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同类化合物

(6R,7R)-7-苯基乙酰胺基-3-[(Z)-2-(4-甲基噻唑-5-基)乙烯基]-3-头孢唑啉-4-羧酸二苯甲基酯 顺式-4-(2,2-二甲氧基乙基)-3-邻苯二甲酰-2-氮杂环丁酮 顺式-3-氨基-1-(2,4-二甲氧基苄基)-4-甲氧羰基-2-氮杂环丁酮 顺式-1-(对甲苯基)-3-苄氧基-4-(对茴香基)-氮杂环丁烷-2-酮 顺式-1,4-二苯基-3-(甲基苯基氨基)-2-氮杂环丁酮 青霉酰聚赖氨酸 青霉素钾 青霉素钠 青霉素酶液体 青霉素杂质F氢化物 青霉素杂质C 青霉素亚砜酯(GESO) 青霉素V二苄乙二胺 青霉素G衍生物 青霉素G甲酯 青霉素G甲酯 青霉素G-D7 青霉素 V 钠 阿那白滞素 阿莫西林钠 阿莫西林三水合物 阿莫西林 阿立必利D5 阿度西林 铜(2+)酞菁-29,30-二负离子-2-(二甲氨基)乙醇(1:1:1) 钾(2S,5R,6R)-6-[[2-[(E)-3-氯丁-2-烯基]巯基乙酰基]氨基]-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸酯 钠6-[[3-(2-氯-6-氟苯基)-5-甲基1,2-恶唑-4-羰基]氨基]-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸盐水合物 钠(6S,7R)-3-(羟基甲基)-7-甲氧基-8-氧代-7-[(2-噻吩基乙酰基)氨基]-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸酯 钠(6R,7R)-7-[[(2Z)-2-(2-氨基-1,3-噻唑-4-基)-2-甲氧基亚氨基乙酰基]氨基]-8-氧代-3-[(2S)-四氢呋喃-2-基]-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸酯 钠(2S,5R,6R)-6-[(2-叠氮基-2-苯基乙酰基)氨基]-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸盐 酞氨西林 赖氨酸氯尼辛 萘夫西林钠 萘夫西林钠 萘夫西林杂质 苯磺酸,2-[(2-羟基-1-萘基)偶氮]-5-甲基-,盐(2:1)钡 苯甘孢霉素亚砜 苯氧乙基青霉素钾 苯并[b]噻吩-3-羧酸,2-[3-氯-2-(4-硝基苯基)-4-羰基-1-吖丁啶基]-4,5,6,7-四氢-,乙基酯 苯唑西林钠 苯唑西林杂质1 舒巴坦杂质19 舒他西林 脱乙酰基戊二酰 7-氨基头孢烷酸 脱乙酰基头孢噻肟 肟莫南 羰苄西林苯酯钠 美罗培南钠盐 美罗培南 美洛培南