2-氨基-2,6,6-三甲基双环[3.1.1]庚烷-3-羧酸 | 705948-99-8

• 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: 2-氨基-2,6,6-三甲基双环[3.1.1]庚烷-3-羧酸
• 中文别名: 二环[2.2.1]庚-5-烯-2-胺,3-(1-甲基乙基)-,(2-endo,3-exo)-(9CI)；丁腈，2-甲氧基-3-氧-(9CI)
• 英文名称: (1R,2R,3S,5R)-2-amino-2,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylic acid
• CAS: 705948-99-8
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: RVNVDAUGIAPWLP-RFOGZPIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (1R,2R,3S,5R)-2-aminopinane-3-carboxylate 在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 2-氨基-2,6,6-三甲基双环[3.1.1]庚烷-3-羧酸
  参考文献：
  名称：

  Derivatives of pinane amino acids as new anticonvulsants

  摘要：

  DOI：

  10.1134/s0012500808100029

文献信息

• Unusual Temperature-Induced Retention Behavior of Constrained β-Amino Acid Enantiomers on the Zwitterionic Chiral Stationary Phases ZWIX(+) and ZWIX(-)
  作者：István Ilisz、Zoltán Pataj、Zsanett Gecse、Zsolt Szakonyi、Ferenc Fülöp、Wolfgang Lindner、Antal Péter

  DOI：10.1002/chir.22333

  日期：2014.8

  The effects of temperature on the chiral recognition of cyclic β‐amino acid enantiomers on zwitterionic [Chiralpak ZWIX(+) and ZWIX(–)] chiral stationary phases were investigated. Experiments were performed at different mobile phase compositions and under 10°C column temperature increments in the temperature range 10–50°C. Apparent thermodynamic parameters and Tiso values were calculated from plots

  研究了温度对两性离子型[Chiralpak ZWIX（+）和ZWIX（-）]手性固定相上环状β-氨基酸对映体的手性识别的影响。实验是在不同的流动相组成下，在10°C的柱温下，在10–50°C的温度范围内进行的。根据ln k和lnα与1 / T的关系图计算了表观热力学参数和T iso值，分别。观察到异常的温度行为，尤其是在ZWIX（–）色谱柱上，在该色谱柱上使用包含25 mM三乙胺和50 mM甲酸作为流动相的MeOH / MeCN（50/50 v / v）导致了非线性Van't Hoff图并随着温度的升高而延长保留时间。在两根色谱柱上，均观察到了焓和熵驱动的分离。手性26：385–393，2014。©2014 Wiley Periodicals，Inc.
• Synthesis, Antimicrobial Evaluation, and Structure–Activity Relationship of α-Pinene Derivatives
  作者：Preeti Dhar、PuiYee Chan、Daniel T. Cohen、Fadi Khawam、Sarah Gibbons、Teresa Snyder-Leiby、Ellen Dickstein、Prashant Kumar Rai、Geeta Watal

  DOI：10.1021/jf403586t

  日期：2014.4.23

  Several (+)- and (-)-alpha-pinene derivatives were synthesized and evaluated for their antimicrobial activity toward Gram-positive bacteria Micrococcus luteus and Staphylococcus aureus, Gram-negative bacterium Escherichia coli, and the unicellular fungus Candida albicans using bioautographic assays. (+)-alpha-Pinene 1a showed modest activity against the test organisms, whereas (-)-alpha-pinene 1b showed no activity at the tested concentration. Of all the alpha-pinene derivatives evaluated, the beta-lactam derivatives (10a and 10b) were the most antimicrobial. The increase in the antimicrobial activity of 10a compared to la ranged from nearly 3.5-fold (C. albicans) to 43-fold (S. aureus). The mean +/- standard deviation for the zone of inhibition (mm) for 10a (C. albicans) was 31.9 +/- 4.3 and that for S. aureus was 51.1 +/- 2.9. Although (-)-alpha-pinene 1b was not active toward the test microorganisms, the corresponding beta-lactam 10b, amino ester 13b, and amino alcohol 14b showed antimicrobial activity toward the test microorganisms. The increase in the antimicrobial activity of lob compared to 1b ranged from 32-fold (S. aureus) to 73-fold (M. luteus). The mean +/- standard deviation for the zone of inhibition (mm) for 10b (S. aureus) was 32.0 +/- 0.60 and that for M. luteus was 73.2 +/- 0.30.