Ethyl (2S,E)-1-(tert-butoxycarbonyl)-4-ethylidenepyroglutamate | 169337-96-6

• 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: Ethyl (2S,E)-1-(tert-butoxycarbonyl)-4-ethylidenepyroglutamate
• 英文别名: 1-O-tert-butyl 2-O-ethyl (2S,4E)-4-ethylidene-5-oxopyrrolidine-1,2-dicarboxylate
• CAS: 169337-96-6
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: CTFMTEYVUTZBHA-ZKXNXJMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl (2S,E)-1-(tert-butoxycarbonyl)-4-ethylidenepyroglutamate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-2-tert-Butoxycarbonylamino-4-eth-(E)-ylidene-pentanedioic acid
  参考文献：
  名称：

  4-Alkylidenyl glutamic acids, potent and selective GluR5 agonists

  摘要：

  Twenty-four 4-alkylidene glutamic acids were synthesised and tested as potential subtype selective GluR5 and 6 ligands. It was found that a critical size of alkylidene group gave potent and selective GluR5 receptor agonists. LY339624 had K(i)s of 0.0326 and >100 mu M on GluR5 and 6 receptors, respectively. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00346-2
• 作为产物：
  描述：

  BOC-L-焦谷氨酸乙酯 在 甲基磺酰氯 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 Ethyl (2S,E)-1-(tert-butoxycarbonyl)-4-ethylidenepyroglutamate
  参考文献：
  名称：

  4-Alkylidenyl glutamic acids, potent and selective GluR5 agonists

  摘要：

  Twenty-four 4-alkylidene glutamic acids were synthesised and tested as potential subtype selective GluR5 and 6 ligands. It was found that a critical size of alkylidene group gave potent and selective GluR5 receptor agonists. LY339624 had K(i)s of 0.0326 and >100 mu M on GluR5 and 6 receptors, respectively. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00346-2

文献信息

• Synthesis of Enantiomerically Pure 4-Substituted Glutamic Acids and Prolines: General Aldol Reaction of Pyroglutamate Lactam Lithium Enolate Mediated by Et2O.cntdot.BF3
  作者：Jesus Ezquerra、Concepcion Pedregal、Belen Yruretagoyena、Almudena Rubio、M. Carmen Carreno、Ana Escribano、Jose Luis Garcia Ruano

  DOI：10.1021/jo00114a054

  日期：1995.5