methyl (1S,2R,4S)-2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate | 139237-37-9

• 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 (1S,2R,4S)-2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate
• 英文别名: methyl (1S,2R,4S)-2-acetamidobicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 139237-37-9
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: RUTMULAEKSLWQD-IQJOONFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,4S)-2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 以87%的产率得到(1R,2R,4S)-methyl 1-acetylaminocyclopentane-1,2,4-tricarboxylate
  参考文献：
  名称：

  1-Aminocyclopentane-1,2,4-tricarboxylic acids screening on glutamatergic and serotonergic systems

  摘要：

  Enantiopure constrained 1-aminocyclopentane-1,2,4-tricarboxylic acids containing the glutamic acid skeleton were prepared as two diastereomers characterized by having the carboxylic groups in position two and four cis-oriented to each other and trans with respect to 1-carboxylic group and all cis-oriented carboxylic groups, respectively. A biochemical screening of activity of the above amino acids was investigated on glutamate and 5-HT receptors to find a possible metabotropic agonist, acting on the serotoninergic system. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.004
• 作为产物：
  描述：

  甲醇 、 (1S,2R,4S)-2-acetylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 在 氯化亚砜 作用下， 反应 20.0h， 以85%的产率得到methyl (1S,2R,4S)-2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate
  参考文献：
  名称：

  1-Aminocyclopentane-1,2,4-tricarboxylic acids screening on glutamatergic and serotonergic systems

  摘要：

  Enantiopure constrained 1-aminocyclopentane-1,2,4-tricarboxylic acids containing the glutamic acid skeleton were prepared as two diastereomers characterized by having the carboxylic groups in position two and four cis-oriented to each other and trans with respect to 1-carboxylic group and all cis-oriented carboxylic groups, respectively. A biochemical screening of activity of the above amino acids was investigated on glutamate and 5-HT receptors to find a possible metabotropic agonist, acting on the serotoninergic system. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.004

文献信息

• Asymmetric synthesis of 2-exo-aminonorbornane-2-endo-carboxylic acid derivatives
  作者：Carlos Cativiela、Pilar López、José A. Mayoral

  DOI：10.1016/s0957-4166(00)82170-9

  日期：1991.1

  The Diels-Alder reaction of cyclopentadiene with N-acetyl-alpha,beta-didehydroalaninate of (-)-cis-3-hydroxy isobornyl neopentyl ether yields the corresponding 2-endo(exo)-acetamido-5-norbornene-2-exo(endo)-carboxylates with total diastereofacial selectivity and with a preference for the cycloadduct with the ester group placed at the endo position. So this dienophile is complementary with the previously described (-)-menthyl N-acetyl-alpha,beta-didehydroalaninate for the asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids, since with the latter dienophile exo cycloadducts are preferably obtained with a high diastereofacial selectivity.
• Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction
  作者：Carlos Cativiela、Pilar López、José A. Mayoral

  DOI：10.1016/s0957-4166(00)80027-0

  日期：1991.1

  The reaction between methyl N-acetyl-alpha,beta-didehydroalaninate and cyclopentadiene in the presence of several chiral Lewis acids is studied and the results obtained are compared with those described for the reactions of the same diene with chiral N-acetyl-alpha,beta-didehydroalaninates. In the presence of the titanium complex 24d methyl (1R, 2R, 4R) 2-acetamido-5-norbornen-2-carboxylate is preferably obtained. Thus, the reaction between methyl N-acetyl-alpha,beta-didehydroalaninate and cyclopentadiene is a good method for the synthesis of (1S, 2R, 4R) 2-aminonorbornane-2-carboxylic acid.
• 1-Aminocyclopentane-1,2,4-tricarboxylic acids screening on glutamatergic and serotonergic systems
  作者：Maria Luisa Gelmi、Francesco Caputo、Francesca Clerici、Sara Pellegrino、Gino Giannaccini、Laura Betti、Laura Fabbrini、Lara Schmid、Lionella Palego、Antonio Lucacchini

  DOI：10.1016/j.bmc.2007.09.004

  日期：2007.12

  Enantiopure constrained 1-aminocyclopentane-1,2,4-tricarboxylic acids containing the glutamic acid skeleton were prepared as two diastereomers characterized by having the carboxylic groups in position two and four cis-oriented to each other and trans with respect to 1-carboxylic group and all cis-oriented carboxylic groups, respectively. A biochemical screening of activity of the above amino acids was investigated on glutamate and 5-HT receptors to find a possible metabotropic agonist, acting on the serotoninergic system. (c) 2007 Elsevier Ltd. All rights reserved.