4-(4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)benzoic acid | 877154-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-(4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)benzoic acid
• 英文别名: 4-[(1R,2S,6R,7S)-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl]benzoic acid
• CAS: 877154-50-2
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: LDROEGNGJDUHCF-CUFDPUGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)benzoic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 4-(4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)benzoic acid chloride
  参考文献：
  名称：

  质子化氨基酸诱导的具有Monoaza-18-crown-6链坠的聚降冰片烯的单手螺旋

  摘要：

  与质子化的氨基酸络合后，获得附有monoaza-18-crown-6（7a）的单手螺旋聚降冰片烯。观察到的合作性是由军士士兵效应和多数规则所揭示的。当使用位阻氨基酸（如苯丙氨酸，异缬氨酸或脯氨酸），氨基酸的酯和氨基醇时，CD光谱中的Δε值会大大降低。质子化的铵离子可与冠醚部分形成配合物，而羧酸可与相邻的冠醚侧基形成氢键，导致侧基的单向取向，从而导致螺旋支架。相应的二聚体10具有与聚降冰片烯7a相同的全同立构立体化学质子化的丙氨酸处理后的行为类似，表现出双信号CD曲线。另一方面，在相同条件下，聚降冰片烯与monoaza-15-crown-5（7b）不会表现出任何CD反应。

  DOI：

  10.1021/ma1014726
• 作为产物：
  描述：

  4-(4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)benzaldehyde 在 氢氧化钾 、 sodium hydroxide 作用下， 反应 0.08h， 以75%的产率得到4-(4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)benzoic acid
  参考文献：
  名称：

  关于带有偶极侧基的聚降冰片烯的刚度。

  摘要：

  通过在钌卡宾络合物（Grubbs I）催化下的开环复分解聚合反应，合成了一系列在C-5,6位具有稠合偶极侧基的聚降冰片烯（PNBs）。光物理研究，EFISH测量和原子力显微镜图像已用于研究这些聚合物的结构和形态。这些结果表明聚合物可以采用刚性的棒状结构。对于聚合物的刚性，PNB中双键的存在似乎是必不可少的。不饱和侧基之间的相互作用可能导致相干排列，从而形成棒状结构。

  DOI：

  10.1002/chem.200500770

文献信息

• Coherently Aligned Porphyrin-Appended Polynorbornenes
  作者：Hsian-Wen Wang、Zhi-Chang Liu、Chih-Hsien Chen、Tsong-Shin Lim、Wunshain Fann、Chih-Gang Chao、Jian-Yuan Yu、Shern-Long Lee、Chun-hsien Chen、Shou-Ling Huang、Tien-Yau Luh

  DOI：10.1002/chem.200900195

  日期：2009.6.2

  You can append on me! Porphyrin‐appended polynorbornenes derived from 5,6‐endo‐fused N‐arylpyrrolidenonorbornenes have been shown to have coherently aligned pendant groups that exhibit exciton coupling and fluorescence quenching in the absorption and emission profiles (see figure).

  你可以加在我身上！卟啉所附聚降冰片烯5,6-从衍生内切-融合Ñ -arylpyrrolidenonorbornenes已经显示出具有相干对齐的侧基，在吸收和发射分布表现出激子耦合和荧光淬灭（参见图）。
• Unsymmetrical Polymeric Ladderphanes by Sequential Polymerization: A New Approach for the Template Synthesis of Polymers with Well-Defined Chain Length and Narrow Polydispersity
  作者：Yuan-Zhen Ke、Shern-Long Lee、Chun-hsien Chen、Tien-Yau Luh

  DOI：10.1002/asia.201000877

  日期：2011.7.4

  Nothing ROMP with that: Unsymmetrical double‐stranded ladderphanes are obtained by sequential ring‐opening metathesis polymerization and Glaser oxidation of norbornene appended with bisalkyne moieties. Hydrolysis of these ladderphanes gives substituted poly(m‐phenylene butadiynylene)s with narrow polymer dispersity index (PDI) and well‐controlled degree of polymerization.

  ROMP没什么：通过顺序开环易位聚合和降冰片烯与双炔烃部分连接的Glaser氧化获得不对称的双链梯形。这些ladderphanes的水解得到取代的聚（米亚苯基butadiynylene）■具有窄分散度聚合物指数（PDI）和聚合的良好控制的程度。
• Hydrogen-Bonding Induced Cooperative Effect on the Energy Transfer in Helical Polynorbornenes Appended with Porphyrin-Containing Amidic Alanine Linkers
  作者：Zhi-Chang Liu、Chih-Hsien Chen、Hsian-Wen Wang、Yen-Chin Huang、Ming-Jui Kao、Tsong-Shin Lim、Tien-Yau Luh

  DOI：10.1002/asia.200900567

  日期：2010.4.15

  Polynorbornenes appended with porphyrins containing a range of different linkers are synthesized. The use of bisamidic chiral alanine linkers between the pending porphyrins and the polymeric backbone has been shown to bring the adjacent porphyrin chromophores to more suitable orientation for exciton coupling owing to hydrogen bonding between the adjacent linkers. The hydrogen bonding between the adjacent

  合成了附有含一系列不同接头的卟啉的聚降冰片烯。已显示在未决的卟啉和聚合物骨架之间使用双酰胺手性丙氨酸连接基，由于相邻连接基之间的氢键作用，使相邻的卟啉生色团更适合于激子偶联。这些聚合物中相邻侧基之间的氢键可能引起协同效应，因此使这些聚合物具有单手螺旋结构。这种协同作用反映在无规共聚物中锌-卟啉和游离碱卟啉之间的FRET效率的提高上。
• Triple-Stranded Polymeric Ladderphanes
  作者：Kwang-Wei Yang、Jun Xu、Chih-Hsien Chen、Hsin-Hua Huang、Tony Jian-Yuan Yu、Tsong-Shin Lim、Chun-hsien Chen、Tien-Yau Luh

  DOI：10.1021/ma100550q

  日期：2010.6.22

  The first triple-stranded polymeric ladderphanes 6 with multilayer planar oligoaryl linkers having C-3 symmetry are synthesized by Grubbs I catalyst-mediated ring-opening metathesis of tris-norbornene derivatives 5. All linkers are coherently aligned perpendicular to the longitudinal axis of the polymer. Interactions between these linkers lead to fluorescence quenching or perturbation of frontier orbitals, resulting in shift of the emission maximum. These triple-stranded polymeric ladderphanes tend to self-assemble to form an ordered pattern as revealed by TMAFM.
• Polymeric Ladderphanes
  作者：Chih-Ming Chou、Shern-Long Lee、Chih-Hsien Chen、Akkattu Thankappan Biju、Hsian-Wen Wang、Yi-Lin Wu、Guo-Fu Zhang、Kuang-Wei Yang、Tsong-Shin Lim、Min-Jie Huang、Po-Yu Tsai、Kin-Chuan Lin、Shou-Ling Huang、Chun-hsien Chen、Tien-Yau Luh

  DOI：10.1021/ja9035362

  日期：2009.9.9

  A new class of polymers, which have a double-stranded polybinorbornene skeleton with multilayer planar oligoaryl linkers, defined as polymeric ladderphanes, are synthesized. The structures of these ladderphanes are determined by spectroscopic means. Photophysical studies and time-resolved fluorescence spectroscopic investigations reveal that there is a strong interaction between the chromophore linkers. Thus, Sorel band splitting in the absorption spectrum of the polymer with porphyrin linker (12e), significant fluorescence quenching with oligoaryl linkers (12b-d), and excimer emission with a terphenylene-diethynylene linker (12a) are characteristic photophysical properties of these polymers. Scanning tunneling microscopy shows that polymers 12b and d exhibit a ladder-like morphology and form a supramolecular assembly leading to a two-dimensional ordered array on a highly oriented pyrolytic graphite surface.