(2R,3R)-3-amino-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine-2-sulfonic acid tetrabutylammonium salt | 180468-20-6

• 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: (2R,3R)-3-amino-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine-2-sulfonic acid tetrabutylammonium salt
• 英文别名: (2R,3R)-3-amino-1-(1-methoxy-3-methyl-1-oxobut-2-en-2-yl)-4-oxoazetidine-2-sulfonic acid
• CAS: 180468-20-6
• 化学式: C₉H₁₄N₂O₆S
• 分子量: 278.286
• InChiKey: FXQNDTLULYHQIY-SVGQVSJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-methylphenyl)-4-formylsydnone 、 (2R,3R)-3-amino-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine-2-sulfonic acid tetrabutylammonium salt 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2R,3S)-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxo-3-[(5-oxo-3-p-tolyl-[1,2,3]oxodiazolydin-4-yl-methylene)-amino]-azetidine-2-sulfonic acid
  参考文献：
  名称：

  顺式-3-氨基-4-氧-氮杂环丁烷-2-磺酸的区域选择性差向异构化和单环β-内酰胺的合成

  摘要：

  描述了一种将顺式-3-氨基-4-氧代-氮杂环丁烷-2-磺酸（3-AAA）区域选择性差向异构化成反式异构体的新方法。发现在席夫碱的形成过程中，顺式-3-AAA的C-3构型完全反转。Schiff碱的亚胺键在甲醇中的裂解导致以高收率生成反式-3-AAA。这里还描述了在氮杂环丁酮氮上具有氨基磺酸基团的新型顺式和反式单bactams的制备。

  DOI：

  10.1016/s0040-4020(00)00298-2
• 作为产物：
  描述：

  2-[(2R,3R)-2-Methoxysulfonyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-2-enoic acid methyl ester 反应 336.0h， 以57.3%的产率得到(2R,3R)-3-amino-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine-2-sulfonic acid tetrabutylammonium salt
  参考文献：
  名称：

  (2R,3R)-3-Ammonio-1-(1-methoxycarbonyl-2-methyl-1-propenyl)-4-oxoazetidine-2-sulfonate Monohydrate: a New Chiral β-Lactam Synthon

  摘要：

  The title compound, a novel monocyclic beta-lactam, was prepared and chemically characterized by IR and H-1 NMR spectroscopy and X-ray structure analysis. C9H14N2O6S.H2O exists as a zwitterion crystallized with a water molecule. The four-membered lactam ring is slightly puckered, the ammonio and sulfonate groups are cis, and the aliphatic substituent is trans to these polar groups. Hydrogen bonds link the zwitterions and the water molecules into spirals parallel to the b axis, forming a two-dimensional network with base vectors along (100) and (010).

  DOI：

  10.1107/s0108270195014077

文献信息

• Mandic, Zorica; Kovacevic, Mice, Croatica Chemica Acta, 1996, vol. 69, # 2, p. 661 - 667
  作者：Mandic, Zorica、Kovacevic, Mice

  DOI：——

  日期：——
• Regioselective Epimerisation of cis-3-Amino-4-oxo-azetidine-2-sulphonic acid and Synthesis of Monocyclic β-Lactams
  作者：Helena Cerić、Miće Kovačević、Marija Šindler-Kulyk

  DOI：10.1016/s0040-4020(00)00298-2

  日期：2000.6

  A novel procedure for the regioselective epimerisation of cis-3-amino-4-oxo-azetidine-2-sulphonic acid (3-AAA) into the trans-isomer is described. It was found that a complete inversion of C-3 configuration of the cis-3-AAA takes place during the formation of a Schiff base. The cleavage of the imine bond of the Schiff base in methanol resulted in the generation of trans-3-AAA in good yield. Here is

  描述了一种将顺式-3-氨基-4-氧代-氮杂环丁烷-2-磺酸（3-AAA）区域选择性差向异构化成反式异构体的新方法。发现在席夫碱的形成过程中，顺式-3-AAA的C-3构型完全反转。Schiff碱的亚胺键在甲醇中的裂解导致以高收率生成反式-3-AAA。这里还描述了在氮杂环丁酮氮上具有氨基磺酸基团的新型顺式和反式单bactams的制备。
• (2R,3R)-3-Ammonio-1-(1-methoxycarbonyl-2-methyl-1-propenyl)-4-oxoazetidine-2-sulfonate Monohydrate: a New Chiral β-Lactam Synthon
  作者：Z. Mandic、R. Kiralj、B. Kojic-Prodic、M. Kovacevic

  DOI：10.1107/s0108270195014077

  日期：1996.4.15

  The title compound, a novel monocyclic beta-lactam, was prepared and chemically characterized by IR and H-1 NMR spectroscopy and X-ray structure analysis. C9H14N2O6S.H2O exists as a zwitterion crystallized with a water molecule. The four-membered lactam ring is slightly puckered, the ammonio and sulfonate groups are cis, and the aliphatic substituent is trans to these polar groups. Hydrogen bonds link the zwitterions and the water molecules into spirals parallel to the b axis, forming a two-dimensional network with base vectors along (100) and (010).