1,2-Cyclopropanedicarboxylic acid,3-[(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethoxy-2-oxoethyl]-,monoethyl ester, (1R,2R,3S)- | 836671-38-6

• 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: 1,2-Cyclopropanedicarboxylic acid,3-[(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethoxy-2-oxoethyl]-,monoethyl ester, (1R,2R,3S)-
• 英文别名: (1R,2R,3S)-3-((S)-tert-Butoxycarbonylamino-ethoxycarbonyl-methyl)-cyclopropane-1,2-dicarboxylic acid monoethyl ester
• CAS: 836671-38-6
• 化学式: C₁₆H₂₅NO₈
• 分子量: 359.376
• InChiKey: BKNCZOAJIBKCNM-ZDCRXTMVSA-N

物化性质

• 沸点：
  497.0±40.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  128.23
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,2-Cyclopropanedicarboxylic acid,3-[(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethoxy-2-oxoethyl]-,monoethyl ester, (1R,2R,3S)- 在 sodium borotritide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  (2S,1′S,2′R,3′R)-2(2′-Carboxy-3′-hydroxymethylcyclopropyl)glycine-[3H], a potent and selective radioligand for labeling group 2 and 3 metabotropic glutamate receptors

  摘要：

  We report herein the synthesis of the tritium labeled isotopomer of 1 and its use as a radioligand to label mGlu8 receptors in rat forebrain membranes as well as cloned human recombinant mGlu receptors. [H-3]-1 was synthesized by the NaBT4 reduction of an activated analog of 5. [H-3]-1 bound appreciably to recombinant human mGlu2, mGlu3 and mGlu8 receptors and to rat forebrain membranes and was displaced by L-glutamate and L-(+)-2 amino-4-phosphonobutyric acid. The results indicate that [H-3]-1 should be a useful ligand for the study of mGluR2, 3, and 8 receptors in cloned cell lines and possibly brain tissue. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.093
• 作为产物：
  描述：

  ethyl (2S,1'S,2'R,3'R)-N-(tert-butoxycarbonyl)-2-(2'-ethoxycarbonyl-3'-hydroxymethylcyclopropyl) glycinate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 为溶剂， 生成 ethyl 3-tert-butoxycarbonyl-4-oxo-3-azabicyclo[3.1.0]hexane-2,6-dicarboxylate 、 1,2-Cyclopropanedicarboxylic acid,3-[(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethoxy-2-oxoethyl]-,monoethyl ester, (1R,2R,3S)-
  参考文献：
  名称：

  (2S,1′S,2′R,3′R)-2(2′-Carboxy-3′-hydroxymethylcyclopropyl)glycine-[3H], a potent and selective radioligand for labeling group 2 and 3 metabotropic glutamate receptors

  摘要：

  We report herein the synthesis of the tritium labeled isotopomer of 1 and its use as a radioligand to label mGlu8 receptors in rat forebrain membranes as well as cloned human recombinant mGlu receptors. [H-3]-1 was synthesized by the NaBT4 reduction of an activated analog of 5. [H-3]-1 bound appreciably to recombinant human mGlu2, mGlu3 and mGlu8 receptors and to rat forebrain membranes and was displaced by L-glutamate and L-(+)-2 amino-4-phosphonobutyric acid. The results indicate that [H-3]-1 should be a useful ligand for the study of mGluR2, 3, and 8 receptors in cloned cell lines and possibly brain tissue. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.093