1-(Benzhydrylidene-amino)-cyclopent-3-ene-1,3-dicarboxylic acid 3-ethyl ester 1-methyl ester | 395073-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(Benzhydrylidene-amino)-cyclopent-3-ene-1,3-dicarboxylic acid 3-ethyl ester 1-methyl ester
• 英文别名: 3-O-ethyl 1-O-methyl 1-(benzhydrylideneamino)cyclopent-3-ene-1,3-dicarboxylate
• CAS: 395073-96-8
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: ABOLTXIAOBFMRE-UHFFFAOYSA-N

物化性质

• 沸点：
  478.5±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(Benzhydrylidene-amino)-cyclopent-3-ene-1,3-dicarboxylic acid 3-ethyl ester 1-methyl ester 在 盐酸 、 水 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 43.0h， 生成 (1RS,3SR)-3-ethyl 1-methyl 1-amino-3-benzylcyclopentane-1,3-dicarboxylate
  参考文献：
  名称：

  Synthesis and inhibitory activities at mGluRs of 3-alkylated and N-alkylated cyclopentyl-glutamate analogues

  摘要：

  The conformationally restricted glutamate analogues, 3-alkyl-1-amino-2-cyclopentene-1,3-dicarboxylates and N-alkylated analogues have been prepared in a regioselective and diastereoselective manner. From the biological studies of the 3-alkylated analogues, compound 13b was found to be the most potent antagonist (IC50 7.7 mu M) at mGluR2. Amongst the N-alkylated analogues, compound 20 was found to be a partial agonist (EC50 9.5 mu M) and as well as an antagonist (IC50 47 mu M) at mGluR2. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.054
• 作为产物：
  描述：

  2-丁炔酸乙酯 、 2-[(二苯基亚甲基)氨基]-2-丙酸甲酯 在 三丁基膦 作用下， 以 苯 为溶剂， 反应 24.0h， 以98%的产率得到1-(Benzhydrylidene-amino)-cyclopent-3-ene-1,3-dicarboxylic acid 3-ethyl ester 1-methyl ester
  参考文献：
  名称：

  Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues

  摘要：

  An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 muM) and mGlu2 (EC50 45 muM) receptors.

  DOI：

  10.1021/jo010864i

文献信息

• Synthesis and antagonist activities of 4-aryl-substituted conformationally restricted cyclopentenyl and cyclopentanyl-glutamate analogues
  作者：Alison T. Ung、Stephen G. Pyne、Uta Batenburg-Nguyen、Andrew S. Davis、Azlifa Sherif、François Bischoff、Anne S.J. Lesage

  DOI：10.1016/j.tet.2004.12.024

  日期：2005.2

  The conformationally restricted glutamate analogues, 4-aryl-1-amino-2-cyclopentene-1,3-dicarboxylates and their cyclopentane analogues have been prepared in a diastereoselective manner. Biological studies of 12a and 12b indicates that both compounds are modest antagonists at mGluR2. (C) 2004 Elsevier Ltd. All rights reserved.