5-(anthracen-9-yl)-1H-tetrazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5-(anthracen-9-yl)-1H-tetrazole
• 英文别名: 5-(9-anthracenyl)-1H-tetrazole；5-(9-anthryl)-1H-tetrazole；5-(9-Anthryl)tetrazole；5-anthracen-9-yl-2H-tetrazole
• 化学式: C₁₅H₁₀N₄
• 分子量: 246.271
• InChiKey: XPGRCHBAGKBEAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(anthracen-9-yl)-1H-tetrazole 生成 2H-cyclopentafluorene
  参考文献：
  名称：

  Preparative Methodology and Pyrolytic Behavior of Anthrylmonocarbenes:  Synthesis and Chemistry of 1H-Cyclobuta[de]anthracene

  摘要：

  This study involves (1) the behavior of organolithium reagents (1-6), (2) development of efficient methods for preparing 9(7)- and 1(8)-[methoxy(trimethylsilyl)methyl] anthracenes and their analogues, (3) the intramolecular chemistry of the 9(9)- and 1(l0)-anthrylcarbenes generated by pyrolyses of 7 and 8, respectively, and (4) investigation of thermal behavior and bromination of the 1H-cyclobuta[de]anthracene (11) obtained from 9 or 10. alpha-Methoxy-9-anthrylmethyllithium (1), prepared from 9-(methoxymethyl)anthracene (14) and t-BuLi in TMEDA/Et2O/pentane, reacts at C-10 with D2O, chlorotrimethylsilane, dimethyl sulfate, benzoyl chloride, acetaldehyde, benzaldehyde, and acetone to give, after neutralization, 9,10-dihydro-9-(methoxymethylene)-10-substituted- anthracenes 15 and 21a-f. However, lithiation of 9-(thiomethoxymethyl)anthracene (25) with t-BuLi/TMEDA/Et2O/pentane occurs by an apparent radical-anion displacement process to give 9-anthrylmethyllithium (3), which then reacts with chlorotrimethylsilane to yield 9-(trimethylsilylmethyl)anthracene (28). Similarly, 28 is formed from 25 and from 9-(trimethylsilyloxymethyl)-anthracene (29) with lithium and then chlorotrimethylsilane. The electrophiles D2O, dimethyl sulfate, and benzaldehyde react with 3 at its methyl and its C-10 positions. [Methoxy(trimethylsilyl)methyl]arenes 40-42 and 7 are obtained by reactions of their aryllithium and arylmagnesium bromide precursors with bromo(methoxy)methyltrimethylsilane (39). 1-(Methoxymethyl)anthracene (45) is converted conveniently by t-BuLi and chlorotrimethylsilane to 8. Flash-vacuum pyrolyses of 7 and 8 yield 11 preparatively; 11 then thermolyzes to 2H-cyclopenta[jk]fluorene (46). Decomposition of 9-deuterio-10-[methoxy(trimethylsilyl)methyl]anthracene (55) at 650 degrees C/10(-3) mm results in 10(56)- and 1(57)-deuteriocyclobutanthracenes, thus revealing that the 10-deuterio-9-anthrylcarbene inserts to give 56 and also isomerizes extensively before yielding 57. Of note is that 56 isomerizes thermally by C-10-D movement to form 2-deuteriocyclopentafluorene 58, 57 rearranges by Clo-H movement to yield deuteriocyclopentafluorene 59, and 58 and 59 equilibrate 1,5-sigmatropically. Possible mechanisms for the isomerizations of 56 and 57 are outlined. Further, bromine adds rapidly to 11 to form 9,10-dibromo-9,10-dihydro-1H-cyclobuta[de]anthracene (94), which eliminates HBr on warming to yield 10-bromo-1H-cyclobuta[de]anthracene (95).

  DOI：

  10.1021/jo981105b
• 作为产物：
  描述：

  9-蒽甲醛 在 sodium azide 、 盐酸羟胺 作用下， 以 水 为溶剂， 反应 1.67h， 以81%的产率得到5-(anthracen-9-yl)-1H-tetrazole
  参考文献：
  名称：

  固定在超顺磁性Fe3O4 @ SiO2纳米粒子上的树枝状大分子包裹的Cu（Π）纳米粒子，作为新型可循环利用的催化剂，用于氮杂环的N-芳基化和5取代1H-四唑的绿色合成

  摘要：

  在这项研究中，通过多步合成法制备了固定在超顺磁性Fe 3 O 4 @SiO 2纳米颗粒上的树枝状聚合物包裹的Cu（Π）纳米颗粒。然后，通过多种技术对合成的复合材料进行全面表征，例如傅立叶变换红外（FT-IR）光谱，X射线衍射（XRD），动态光散射（DLS），紫外可见光谱，能量色散X射线分析（ EDX），热重分析（TGA）和振动样品磁力计（VSM）。从获得的信息

  DOI：

  10.1002/aoc.4300

文献信息

• A comparative study between heterogeneous stannous chloride loaded silica nanoparticles and a homogeneous stannous chloride catalyst in the synthesis of 5-substituted 1H-tetrazole
  作者：Arvind Kumar、Satyanand Kumar、Yugal Khajuria、Satish Kumar Awasthi

  DOI：10.1039/c6ra14352k

  日期：——

  Heterogeneous SnCl2–nano-SiO2 efficiently catalyzed 5-substituted 1H-tetrazole synthesis with excellent yield. The catalyst was characterized by using FT-IR, TGA, TEM, and EDX. It is widely applicable on aliphatic, aromatic, heteroaromatic and sterically hindered nitriles with five time recyclability. Being simple and an economically viable approach for the synthesis of SnCl2–nano-SiO2 are additional

  非均相的SnCl 2-纳米SiO 2有效地催化了5-取代的1 H-四唑的合成，并具有优异的收率。通过使用FT-IR，TGA，TEM和EDX对催化剂进行表征。它具有五次循环利用能力，可广泛应用于脂族，芳族，杂芳族和位阻腈。合成SnCl 2-纳米SiO 2的简单方法和经济可行的方法还有其他优点。
• Syntheses of 5-Substituted 1<i>H</i>-Tetrazoles Catalyzed by Reusable CoY Zeolite
  作者：Velladurai Rama、Kuppusamy Kanagaraj、Kasi Pitchumani

  DOI：10.1021/jo201261w

  日期：2011.11.4

  A simple and efficient route for the synthesis of 5-substituted 1H-tetrazoles catalyzed by CoY zeolite is reported. The salient features of this atom-economical, cost-effective, and high-yield cobalt-catalyzed protocol are aerobic conditions, lower reaction time, and milder reaction conditions without additives. Other advantages include experimental ease of manipulation, safer alternative to hazardous

  报道了一种由CoY沸石催化的5-取代的1 H-四唑合成简单有效的途径。这种原子经济，经济高效且高产率的钴催化方案的显着特征是有氧条件，较短的反应时间和无添加剂的较温和的反应条件。其他优点包括实验操作简便，危险，腐蚀性和污染性传统路易斯酸催化剂的更安全替代品，回收率和具有一致催化活性的可重复使用性。通过提出合适的机制使结果合理化。
• Indium-Mediated Cleavage of the Trityl Group from Protected 1H-Tetrazoles
  作者：Cherif Behloul、Miguel Yus、Kenza Bouchelouche、David Guijarro、Francisco Foubelo、Carmen Nájera

  DOI：10.1055/s-0034-1379933

  日期：——

  On treatment with indium metal in MeOH–THF, trityl groups undergo reductive removal from 1H-protected tetrazoles (including aliphatic, aromatic, and heteroaromatic substituents), affording the corresponding free tetrazoles in excellent yields, without any decomposition of the tetrazole ring or reduction of any other group.

  在 MeOH-THF 中用金属铟处理后，三苯甲基从 1H 保护的四唑（包括脂肪族、芳香族和杂芳香族取代基）中还原去除，以优异的产率提供相应的游离四唑，而四唑环没有任何分解或还原任何其他组。
• Zn/MeOH-Mediated Practical and Easy Detritylation of Protected 1-Trityltetrazoles
  作者：Cherif Behloul、Kenza Bouchelouche、Yasmine Hadji、Saadia Benseghir、David Guijarro、Carmen Nájera、Miguel Yus

  DOI：10.1055/s-0035-1561609

  日期：——

  Tsutomu Katsuki Abstract A practical and low-cost method for the detritylation of 1-titryltetrazoles using zinc and methanol is described. This procedure is versatile and efficient in the deprotection of several protected tetrazoles bearing aliphatic, aromatic, and heteroaromatic substituents, as well as some functional groups, without decomposition of the tetrazole ring. A practical and low-cost method for

  献给拉斐尔·乌松（RafaelUsón）教授和克己努（Tsutumu Katsuki） 抽象的 描述了一种实用且低成本的方法，该方法使用锌和甲醇对1-三甲基四氮唑进行三苯甲基脱氨。该方法在脱除几个带有脂族，芳族和杂芳族取代基以及某些官能团的受保护四唑的过程中是通用且有效的，而没有四唑环的分解。 描述了一种实用且低成本的方法，该方法使用锌和甲醇对1-三甲基四氮唑进行三苯甲基脱氨。该方法在脱除几个带有脂族，芳族和杂芳族取代基以及某些官能团的受保护四唑的过程中是通用且有效的，而没有四唑环的分解。
• Sustainable and recyclable magnetic nanocatalyst of 1,10-phenanthroline Pd(0) complex in green synthesis of biaryls and tetrazoles using arylboronic acids as versatile substrates
  作者：Nastaran Bagherzadeh、Ali Reza Sardarian、Hassan Eslahi

  DOI：10.1016/j.mcat.2021.111489

  日期：2021.3