triptycene-9-carboxaldehyde | 1469-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: triptycene-9-carboxaldehyde
• 英文别名: triptycene-9-carbaldehyde；9-(formyl)triptycene；10H-9,10-o-benzeno-anthracene-9-carbaldehyde；10H-9,10-o-Benzeno-anthracen-9-carbaldehyd；Pentacyclo[6.6.6.0(2,7).0(9,14).0(15,20)]icosa-2,4,6,9,11,13,15,17,19-nonaene-1-carbaldehyde；pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene-1-carbaldehyde
• CAS: 1469-54-1
• 化学式: C₂₁H₁₄O
• 分子量: 282.342
• InChiKey: YCUJEHWKRVARJN-UHFFFAOYSA-N

物化性质

• 熔点：
  243-247 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  412.4±44.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  triptycene-9-carboxaldehyde 在 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.75h， 生成 9-ethynyltriptycene
  参考文献：
  名称：

  Molecular Spur Gears Comprising Triptycene Rotators and Bibenzimidazole-Based Stators

  摘要：

  Dynamic gearing of molecular spur gears, the most common type of mechanical gear, is elucidated. Molecular design and conformational analysis show that derivatives of 4,4-bis(triptycen-9-ylethynyl)bibenzimidazole represent suitable constructs to investigate gearing behavior of collateral triptycene (Tp) groups. To test this design, DFT calculations (B97-D/Def2-TZVP) were employed and the results suggest that these molecules undergo geared rotation preferentially to gear slippage. Synthesis of derivatives was carried out, providing a series of molecular spur gears, including the first desymmetrized spur gear molecules, which were subsequently subjected to stereochemical analysis.

  DOI：

  10.1021/ja2063346
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 triptycene-9-carboxaldehyde
  参考文献：
  名称：

  Triptycene 1-Carboxylic Acid and Related Compounds. The Decomposition of Ditriptoyl Peroxide

  摘要：

  DOI：

  10.1021/ja01633a047

文献信息

• Design, Synthesis and Biochemical Evaluation of Novel Ethanoanthracenes and Related Compounds to Target Burkitt’s Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、James P. McKeown、John E. O’Brien、Brendan Twamley、Darren Fayne、D. Clive Williams、Mary J. Meegan

  DOI：10.3390/ph13010016

  日期：——

  Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG-75. Structural modifications were achieved by Diels-Alder

  淋巴瘤（淋巴系统癌）占全世界恶性疾病的12％。伯基特氏淋巴瘤（BL）是非霍奇金淋巴瘤的一种罕见形式，其癌症始于免疫B细胞。我们报告了9,10-dihydro-9,10-ethanananthracene基化合物与抗抑郁药Maprotiline对BL细胞系MUTU-1和DG-75结构相关的化合物的合成和抗增殖活性的初步研究。通过使9-（2-硝基乙烯基）蒽核心与许多亲二烯体包括马来酸酐，马来酰亚胺，丙烯腈和苯炔的狄尔斯-阿尔德反应进行结构修饰。在BL细胞系EBV- MUTU-1和EBV + DG-75（耐化学性）中评估了这些化合物的抗增殖活性。最有效的化合物13j，15、16a，16b，16c，图16d和19a显示的相对于BL细胞系EBV- MUTU-1的IC50值在0.17–0.38μM范围内，相对于耐化学性BL细胞系EBV + DG-75的IC50值在0.45–0.78μM范围内。化合物1
• Synthesis and Structures of 9-Triptycylallene Derivatives
  作者：Gaku Yamamoto、Yuriko Kobayashi、Kasumi Ono、Emiko Yano、Mao Minoura、Yasuhiro Mazaki

  DOI：10.1246/bcsj.79.1293

  日期：2006.8

  9-Triptycylallene (1) was synthesized by LiAlH 4 reduction of l-(9-triptycyl)-2-propynyl methanesulfonate (7), and three 3-substituted derivatives of 1 were also obtained by reacting compound 7 with appropriate metal reagents. LiAlH 4 reduction of 1,3-di(9-triptycyl)-2-propynyl methanesulfonate (10) gave 1,3-di(9-triptycyl)propyne (12). The molecular structures of some of the allenes and of the propyne were

  9-Triptycylallene (1) 通过LiAlH 4 还原1-(9-triptycyl)-2-propynyl methanesulfonate (7) 合成，化合物7 与适当的金属试剂反应也得到1 的三个3-取代衍生物。1,3-二(9-三苯甲基)-2-丙炔基甲磺酸酯(10)的LiAlH 4 还原得到1,3-二(9-三苯甲基)丙炔(12)。一些丙二烯和丙炔的分子结构是通过 X 射线晶体学确定的。同样，丙二烯和一些相关化合物通过核磁共振光谱进行了表征。
• Synthesis and reactions of a monosubstituted dithiirane 1-oxide, 3-(9-triptycyl)dithiirane 1-oxide
  作者：Akihiko Ishii、Tetsuhiko Kawai、Mariko Noji、Juzo Nakayama

  DOI：10.1016/j.tet.2005.05.017

  日期：2005.7

  A 3-monosubstituted dithiirane 1-oxide, 3-(9-triptycyl)dithiirane 1-oxide, was prepared for the first time, by the reaction of (9-triptycyl)diazomethane and S8O. The dithiirane 1-oxide was obtained as cis- and trans-isomers, and the structure of the trans-isomer was verified by X-ray crystallography. The cis-isomer isomerized gradually to the trans-isomer in solution. The divalent sulfur atom of the

  通过（9-三苯甲基）重氮甲烷与S 8 O的反应，首次制备了3-单取代的二噻烷1-氧化物，3-（9-三苯甲基）二硫烷1-氧化物。作为顺式和反式异构体，通过X射线晶体学证实了反式异构体的结构。该顺式异构体逐渐异构化成反式在溶液中异构体。在用三苯基膦处理时，除去了顺式-和反式-二硫杂环丁烷1-氧化物的二价硫原子，分别得到了相应的Z-和E-亚砜。反式的反应（Ph 3 P）2 Pt（C 2 H 4）生成的二硫代环烷一氧化物提供了（磺基-硫代巯基）Pt II配合物，Lawesson试剂生成了1,3,4,2-三硫代磷烷和1,2 ，4,5,3-四硫代磷烷衍生物。
• Spectroscopic studies on effects of triptycyl group on structures and reactivities of triplet arylcarbenes
  作者：Hideo Tomioka、Junichi Nakajima、Hidehiko Mizuno、Eiji Iiba、Katsuyuki Hirai

  DOI：10.1139/cjc-77-5-6-1066

  日期：——

  A series of triplet 9-triptycyl(aryl)carbenes, where aryl groups are phenyl, 1- and 2-naphthyl, and 9-anthryl, is generated by photolysis of the corresponding diazomethanes and observed directly by spectroscopic means. Their structures are characterized by electron spin resonance (ESR) spectroscopy in a 2-methyltetrahydrofuran matrix at 77 K, and the reactivities are investigated by laser flash photolysis

  一系列三线态 9-三苯乙烯基（芳基）卡宾，其中芳基是苯基、1-和 2-萘基以及 9-蒽基，通过相应重氮甲烷的光解产生并通过光谱方法直接观察。它们的结构通过 77 K 下 2-甲基四氢呋喃基质中的电子自旋共振 (ESR) 光谱表征，并且在室温下在脱气苯溶液中通过激光闪光光解研究反应性。将数据与带有一系列取代基（即氢、苯基、萘基和蒽基）的其他芳基卡宾的数据进行比较，揭示了三线态芳基卡宾的结构和反应性之间的有趣关系。
• Thermolysis and photolysis of 1-substituted triptycenes. Divergent fragmentation pathways of the triptycyl skeleton
  作者：Hideo Tomioka、Junichi Nakajima

  DOI：10.1039/p19960000563

  日期：——

  Generation of radical 7 in solution, however, did not result in a similar ring-opening reaction. Irradiation of compounds 1, on the other hand, afforded norcaradienes 3 almost exclusively, obviously as a result of di-π-methane rearrangement. No products resulting from a carbene species proposed to be involved in the di-π-methane reaction of triptycenes were detected. Thermolysis of compounds 3 gave not

  在气相中在600°C / 10 –4 mmHg下热解1-苄基三苯并la不会引起任何明显的分解，但在苄基亚甲基（1b–d）上带有各种取代基（X）的化合物1的类似热解进行得很顺利。分解得到8-苄基苯[ a乙炔基2.解释了该反应的过程，是通过C-X键的均相溶解，然后在所得的苄基7中裂解三苯甲基基团，但是在溶液中生成自由基7并不会导致类似的开环反应。另一方面，辐照化合物1几乎仅提供了正二十碳三烯3，这显然是由于二π甲烷重排的结果。没有发现由提议与三联体的二-π-甲烷反应有关的卡宾物种产生的产物。化合物3的热分解不仅得到化合物2，而且还发现了苯并[ a ]乙炔4和苯并[ a ]茚并[1,2,3- cd ] azulene 5，其组成对取代基（X）和取代基X均敏感。热分解温度。