methyl (2S,3S,4S)-3-(2-methoxy-2-oxoethyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylate | 126891-21-2

• 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: methyl (2S,3S,4S)-3-(2-methoxy-2-oxoethyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylate
• CAS: 126891-21-2
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: HTQDJDRSSZJPAJ-ZOWXZIJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4S)-3-(2-methoxy-2-oxoethyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylate 在 barium dihydroxide 作用下， 以60%的产率得到(2S,3S,4S)-3-(羧甲基)-4-(2-甲氧基苯基)吡咯烷-2-羧酸
  参考文献：
  名称：

  Synthesis of new acromelic acid congeners: novel neuroexcitatory amino acids acting on glutamate receptor

  摘要：

  A general synthetic method of acromelic acid congeners was developed. Various C4-substituents of this family was introduced by the substitution reaction of the corresponding tosylate with diaryl copper lithium. Phenyl derivative 11 showed comparable excitatory activity with kainic acid, and o-anisyl derivative 12 had most potent activity in this family.

  DOI：

  10.1016/s0040-4039(00)78802-2
• 作为产物：
  描述：

  L-羟基脯氨酸 在 palladium on activated charcoal 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 氢氧化钾 、 重铬酸吡啶 、 次氯酸叔丁酯 、 偶氮二异丁腈 、 dimethyl sulfide borane 、 四丁基氟化铵 、 氢气 、 三正丁基氢锡 、 N,N-二甲基苯胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 生成 methyl (2S,3S,4S)-3-(2-methoxy-2-oxoethyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of new acromelic acid congeners: novel neuroexcitatory amino acids acting on glutamate receptor

  摘要：

  A general synthetic method of acromelic acid congeners was developed. Various C4-substituents of this family was introduced by the substitution reaction of the corresponding tosylate with diaryl copper lithium. Phenyl derivative 11 showed comparable excitatory activity with kainic acid, and o-anisyl derivative 12 had most potent activity in this family.

  DOI：

  10.1016/s0040-4039(00)78802-2

文献信息

• An efficient synthesis of 4-aryl kainic acid analogs
  作者：Hiroshi Maeda、Natesan Selvakumar、George A. Kraus

  DOI：10.1016/s0040-4020(98)01101-6

  日期：1999.1

  A synthesis of 4-aryl kainic acid analogs was achieved using a highly stereoselective Michael addition reaction of dimethyl 2-oxoglutarate with a nitrostyrene. Nitro group reduction, deoxygenation and epimerization complete the synthetic route.

  使用2-氧代戊二酸二甲酯与硝基苯乙烯的高度立体选择性迈克尔加成反应实现了4-芳基海藻酸类似物的合成。硝基还原，脱氧和差向异构完成了合成路线。
• Simple analogs of acromelic acid, which are highly active agonists of kainate type neuroexcitant
  作者：Kimiko Hashimoto、Manabu Horikawa、Haruhisa Shirahama

  DOI：10.1016/s0040-4039(00)97239-3

  日期：1990.1
• A Direct Route to Biologically Active Kainic Acid Analogs
  作者：Hiroshi Maeda、George A. Kraus

  DOI：10.1021/jo962114s

  日期：1997.4.1
• Synthesis of new acromelic acid congeners: novel neuroexcitatory amino acids acting on glutamate receptor
  作者：Kimiko Hashimoto、Haruhisa Shirahama

  DOI：10.1016/s0040-4039(00)78802-2

  日期：1991.6

  A general synthetic method of acromelic acid congeners was developed. Various C4-substituents of this family was introduced by the substitution reaction of the corresponding tosylate with diaryl copper lithium. Phenyl derivative 11 showed comparable excitatory activity with kainic acid, and o-anisyl derivative 12 had most potent activity in this family.