N-(tert-Butoxycarbonyl)-4-methylidene-L-glutamic acid | 175088-92-3

• 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-(tert-Butoxycarbonyl)-4-methylidene-L-glutamic acid
• 英文别名: (4S)-2-methylidene-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid
• CAS: 175088-92-3
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: SMUGUEYZXFUXTD-ZETCQYMHSA-N

物化性质

• 沸点：
  499.4±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-Butoxycarbonyl)-4-methylidene-L-glutamic acid 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (S)-4-methylene glutamic 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：

  ethyl N-Boc-4-methylene-L-pyroglutamate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-(tert-Butoxycarbonyl)-4-methylidene-L-glutamic 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

文献信息

• Process for synthesizing L--methylene glutamic acid and analogs
  申请人：——

  公开号：US20040106826A1

  公开（公告）日：2004-06-03

  A process for synthesizing substantially enantiomerically pure L-amino acids, particularly L- -methylene glutamic acid, and esters and salts thereof. The process includes the derivatization of (2S)-pyroglutamic acid, and the decyclization of the resulting derivative to form the desired end product.

  一种合成基本对映纯L-氨基酸的方法，特别是L- -亚甲基谷氨酸及其酯和盐的方法。该方法包括对(2S)-吡咯烷酸进行衍生化，以及对所得衍生物进行去环化反应，形成所需的最终产物。
• PROCESS FOR SYNTHESIZING L-Y-METHYLENE GLUTAMIC ACID AND ANALOGS
  申请人：BIONUMERIK PHARMACEUTICALS, INC.

  公开号：EP1554235A2

  公开（公告）日：2005-07-20
• EP1554235A4
  申请人：——

  公开号：EP1554235A4

  公开（公告）日：2007-04-04
• US6977311B2
  申请人：——

  公开号：US6977311B2

  公开（公告）日：2005-12-20
• [EN] PROCESS FOR SYNTHESIZING L-Y-METHYLENE GLUTAMIC ACID AND ANALOGS<br/>[FR] PROCEDE POUR SYNTHETISER UN ACIDE GLUTAMIQUE DE L-Y-METHYLENE ET ANALOGUES
  申请人：BIONUMERIK PHARMACEUTICALS INC

  公开号：WO2004039314A2

  公开（公告）日：2004-05-13

  A process for synthesizing substantially enantiomerically pure L-amino acids, particularly L- -methylene glutamic acid, and esters and salts thereof. The process includes the derivatization of (2S)-pyroglutamic acid, and the decyclization of the resulting derivative to form the desired end product.