(1R)-2-乙酰氨基双环[2.2.1]庚-5-烯-2-羧酸 | 131053-13-9

• 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
• 中文名称: (1R)-2-乙酰氨基双环[2.2.1]庚-5-烯-2-羧酸
• 英文名称: 2-exo-Acetamidonorbornene-2-endo-carboxylic acid
• 英文别名: (1RS,2SR,4RS)-2-acetylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid；(1R,2S,4R)-2-acetamidobicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS: 131053-13-9；131102-02-8；131102-03-9；131177-83-8；133007-77-9；133007-78-0
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: CISYFNQLQVDBLT-WEDXCCLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-2-乙酰氨基双环[2.2.1]庚-5-烯-2-羧酸 在 三甲基铝 、 sodium methylate 作用下， 生成 2-exo-Acetamido-2-endo-methoxycarbonylmethylthionorbornene
  参考文献：
  名称：

  A two-step synthesis of 2-exo-substituted 2-endo-aminonorbornenes from 2-acetamidonorbornene-2-carboxylic acids

  摘要：

  2-exo-Substituted 2-endo-acetamidonorbornenes (3) were synthesized in a two-step procedure from 2-acetamidonorbornene-2-carboxylic acids (1, 1') with exceedingly high exo-selectives based on a new approach involving anodic decarboxylation followed by organoaluminum-promoted nucleophilic substitution on 2-endo-acetamido-2-exo-methoxynorbornene (2).

  DOI：

  10.1016/s0040-4020(01)87043-5
• 作为产物：
  描述：

  (-)-menthyl N-acetyl-α,β-dehydroalaninate 在 氢氧化钾 、 四氯化钛 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 (1R)-2-乙酰氨基双环[2.2.1]庚-5-烯-2-羧酸
  参考文献：
  名称：

  Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction

  摘要：

  DOI：

  10.1016/s0957-4166(00)86334-x

文献信息

• N-Fmoc-dehydroalanine: a versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids
  作者：Brendan A Burkett、Christina L.L Chai

  DOI：10.1016/s0040-4039(00)01113-8

  日期：2000.8

  The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed.

  描述了通过氧化/消除策略从S-保护的半胱氨酸开始的聚合物负载的N -Fmoc-脱氢丙氨酸的合成。与一系列二烯的环加成以适中的产率提供了一系列构象受限的氨基酸。讨论了这种方法在组合库中的潜在应用。
• 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.
• 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.
• CATIVIELA, CARLOS;LOPEZ, PILAR;MAYORAL, JOSE A., TETRAHEDRON:, 1,(1990) N, C. 61-64
  作者：CATIVIELA, CARLOS、LOPEZ, PILAR、MAYORAL, JOSE A.

  DOI：——

  日期：——
• A two-step synthesis of 2-exo-substituted 2-endo-aminonorbornenes from 2-acetamidonorbornene-2-carboxylic acids
  作者：Hiroyoshi Yamazaki、Hiroshi Horikawa、Takashi Nishitani、Tameo Iwasaki、Kimio Okamura、Tadamasa Date

  DOI：10.1016/s0040-4020(01)87043-5

  日期：1991.1

  2-exo-Substituted 2-endo-acetamidonorbornenes (3) were synthesized in a two-step procedure from 2-acetamidonorbornene-2-carboxylic acids (1, 1') with exceedingly high exo-selectives based on a new approach involving anodic decarboxylation followed by organoaluminum-promoted nucleophilic substitution on 2-endo-acetamido-2-exo-methoxynorbornene (2).