N-tosyl-4-oxoproline methyl ester | 16217-10-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-tosyl-4-oxoproline methyl ester
• 英文别名: 4-Oxo-N-p-toluolsulfonyl-l-prolinmethylester；N-Tosyl-4-oxo-L-prolin-methylester；4-Oxo-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylicacid methyl ester；methyl (2S)-1-(4-methylphenyl)sulfonyl-4-oxopyrrolidine-2-carboxylate
• CAS: 16217-10-0
• 化学式: C₁₃H₁₅NO₅S
• 分子量: 297.332
• InChiKey: JMCBIKYQULEIOX-LBPRGKRZSA-N

物化性质

• 沸点：
  455.0±55.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-tosyl-4-oxoproline methyl ester 在 sodium cyanoborohydride 作用下， 生成 (2S,4S)-4-(Hydroxy-methyl-amino)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Spin labeled hydroxyproline analogues

  摘要：

  The synthesis and properties of both epimers of 4-(N-hydroxyamino)-N-tosyl-L-proline methyl ester and derivatives thereof are reported. In the presence of air, the compounds bearing a free N-hydroxyamino group oxidized in solution to give the corresponding aminoxyl free radicals, EPR spectra of which were recorded. None of these compounds showed any interesting biological activity as such, but they constitute potential synthetic building blocks towards spin labeled glycopeptide or oligopeptide analogues. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00083-x
• 作为产物：
  描述：

  methyl (2S,4R)-4-hydroxy-1-tosylpyrrolidine-2-carboxylate 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以95%的产率得到N-tosyl-4-oxoproline methyl ester
  参考文献：
  名称：

  Design, synthesis and evaluation of novel sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors

  摘要：

  A series of novel sulfonyl pyrrolidine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. Compounds 6a-d were more potent MMP-2 inhibitors than the positive control LY52. The structure-activity relationships were also briefly discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.027

文献信息

• Conversion of 4-Oxoproline Esters to 4-Substituted Pyrrole-2-carboxylic Acid Esters
  作者：Yasushi Arakawa、Naomi Yagi、Yukimi Arakawa、Ken-ichi Tanaka、Shigeyuki Yoshifuji

  DOI：10.1248/cpb.57.167

  日期：——

  The Grignard, Wittig, Tebbe, Horner–Emmons, and Reformatsky reactions of the 4-oxoproline esters gave the corresponding 4-alylated or 4-alkylidenated products, respectively. The products were properly treated with bases to cause aromatization, giving 4-substituted pyrrole-2-carboxylic acid esters such as methyl 4-methylpyrrole-2-carboxylate, which is a trail pheromone of Atta texana.

  4-氧代脯氨酸酯的格氏反应、维蒂希反应、特贝反应、霍纳-埃蒙斯反应和 Reformatsky 反应分别产生了相应的 4-酰化或 4-亚烷基化产物。这些产物经碱适当处理后会发生芳香化反应，产生 4-取代的吡咯-2-羧酸酯，如 4-甲基吡咯-2-羧酸甲酯，这是 Atta texana 的一种踪迹信息素。
• Design, synthesis and evaluation of novel sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors
  作者：Xian-Chao Cheng、Qiang Wang、Hao Fang、Wei Tang、Wen-Fang Xu

  DOI：10.1016/j.bmc.2008.04.027

  日期：2008.5

  A series of novel sulfonyl pyrrolidine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. Compounds 6a-d were more potent MMP-2 inhibitors than the positive control LY52. The structure-activity relationships were also briefly discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• Spin labeled hydroxyproline analogues
  作者：Jean M.J Tronchet、Chantal Jorand、Guido Zosimo-Landolfo、Michel Geoffroy

  DOI：10.1016/s0014-827x(99)00083-x

  日期：1999.9

  The synthesis and properties of both epimers of 4-(N-hydroxyamino)-N-tosyl-L-proline methyl ester and derivatives thereof are reported. In the presence of air, the compounds bearing a free N-hydroxyamino group oxidized in solution to give the corresponding aminoxyl free radicals, EPR spectra of which were recorded. None of these compounds showed any interesting biological activity as such, but they constitute potential synthetic building blocks towards spin labeled glycopeptide or oligopeptide analogues. (C) 1999 Elsevier Science S.A. All rights reserved.