1-azido-2-naphthaldehyde | 172033-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-azido-2-naphthaldehyde
• 英文别名: Formyl-1-naphthyl azide；1-azidonaphthalene-2-carbaldehyde
• CAS: 172033-87-3
• 化学式: C₁₁H₇N₃O
• 分子量: 197.196
• InChiKey: QJAZRYYYLWZRNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-azido-2-naphthaldehyde 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.5h， 生成 (1H-Benzo[g]indol-2-yl)-(4-methoxy-phenyl)-methanone
  参考文献：
  名称：

  Kar, Samiran; Lahiri, Saswati, Journal of the Indian Chemical Society, 1999, vol. 76, # 11-12, p. 607 - 610

  摘要：

  DOI：
• 作为产物：
  描述：

  1-硝基-2-萘醛 在 六甲基磷酰三胺 、 sodium azide 作用下， 以60 %的产率得到1-azido-2-naphthaldehyde
  参考文献：
  名称：

  通过两个串联 [3 + 2] 环加成事件获得的新型双三唑支架，包括未催化的室温叠氮化物-炔烃点击反应

  摘要：

  先前描述的 α-乙酰基-α-重氮甲磺酰胺用于与含叠氮化物的苯甲醛和丙炔胺的三组分反应。除了最初形成三唑核外，反应在室温下以未催化的方式进一步进行，并在分子内叠氮化物-炔烃点击反应后产生结构有趣的新型双三唑。

  DOI：

  10.3762/bjoc.18.175

文献信息

• A facile synthesis of 2H-indazoles under neat conditions and further transformation into aza-γ-carboline alkaloid analogues in a tandem one-pot fashion
  作者：Shinde Vidyacharan、A. Sagar、N. C. Chaitra、Duddu S. Sharada

  DOI：10.1039/c4ra06838f

  日期：——

  We have described a facile, microwave-assisted, catalyst-free and solvent-free approach to 2H-indazoles and further developed a robust tandem one-pot metal-free strategy for C–C bond formation at the C-3 position of 2H-indazoles leading to a unique class of aza-γ-carboline alkaloid analogues. This straightforward expedient synthesis constitutes an interesting alternative to the existing conventional transition metal catalyzed reactions.

  我们描述了一种简便的微波辅助、无催化剂和无溶剂的方法来合成2H-吲哚唑，并进一步开发了一种强健的串联一锅法金属自由策略，用于在2H-吲哚唑的C-3位形成C–C键，从而得到一种独特的氮杂γ-卡宾类生物碱类似物。这种直接的合成方法构成了现有传统过渡金属催化反应的一种有趣替代方案。
• [EN] ANTIVIRAL AGENTS AND USES THEREOF<br/>[FR] AGENTS ANTIVIRAUX ET LEURS UTILISATIONS
  申请人：UNIV GRIFFITH

  公开号：WO2021016670A1

  公开（公告）日：2021-02-04

  The present invention relates to a compound of formula (I), or a pharmaceutically acceptable salt thereof: Formula (I) In which R3 is selected from the group consisting of optionally substituted N-linked naphthotriazole, optionally substituted N-linked indazole, and certain N-linked triazoles. The present invention also relates to uses of the compounds in treating a disease, disorder or condition caused by viral infection, and pharmaceutical compositions comprising the compounds.

  本发明涉及一种化合物，其化学式为(I)，或其药学上可接受的盐：化学式(I) 其中R3选自可选择的取代N-连接的萘三唑、可选择的取代N-连接的吲唑和某些N-连接的三唑组成的群。本发明还涉及将该化合物用于治疗由病毒感染引起的疾病、疾病或病况的用途，以及包含该化合物的药物组合物。
• 1- and 3-Nitreno-2-naphthylcarbenes. A Combined Experimental and Computational Study
  作者：Hideo Tomioka、Norio Nakane、Jiro Tatsugi

  DOI：10.1246/bcsj.81.1629

  日期：2008.12.15

  The structures, energies, and thermal stabilities of E and Z isomers of a singlet, a triplet, and a quintet states of naphthalene bearing nitrene and carbene units on adjacent (1,2- and 3,2-) positions were examined by DFT methods. For both 1,2- and 3,2-isomers, singlet quinoidal diradicals were predicted to be the ground state with the corresponding triplet state lying slightly higher in energy. The quintet state of the 1,2-isomer was found to lie approximately 30 kcal mol−1 (1 kcal = 4.184 kJ) above the ground state, while that of the 3,2-isomer was predicted to lie only 9 kcal mol−1 above the ground state. This difference is discussed in terms of loss of energy due to aromaticity between the two isomers. Thermal stability of the ground state in terms of ring-opening and -closure reactions indicated that both isomers prefer to decay by the latter process forming naphtho[b]azetes. Attempts to generate and characterize the ground state quionoidal diradical by matrix IR spectroscopic methods in Ar at low temperature all resulted in the detection of the azete.

  通过 DFT 方法研究了在相邻（1,2- 和 3,2-）位置上含有腈和碳单元的萘的单线态、三线态和五线态的 E 和 Z 异构体的结构、能量和热稳定性。对于 1,2- 和 3,2- 异构体来说，单复数二价二叉态被预测为基态，相应的三重态能量稍高。研究发现，1,2-异构体的五重态比基态高出约 30 kcal mol-1（1 kcal = 4.184 kJ），而 3,2- 异构体的五重态仅比基态高出 9 kcal mol-1。我们将从这两种异构体之间的芳香性导致的能量损失的角度来讨论这种差异。基态在开环和闭环反应中的热稳定性表明，这两种异构体更倾向于通过后一过程衰变，形成萘并[b]氮杂环丁烷。尝试在低温下用矩阵红外光谱法在氩气中生成基态的类醌二极体并描述其特征，结果都检测到了氮杂环丁烷。
• A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction
  作者：Ksenia Malkova、Andrey Bubyrev、Vasilisa Krivovicheva、Dmitry Dar’in、Alexander Bunev、Mikhail Krasavin

  DOI：10.3762/bjoc.18.175

  日期：——

  described α-acetyl-α-diazomethanesulfonamide was employed in a three-component reaction with azide-containing benzaldehydes and propargylamines. Besides the initial formation of the triazole core, the reaction proceeded further, in uncatalyzed fashion at room temperature and yielded, after intramolecular azide–alkyne click reaction novel, structurally intriguing bistriazoles.

  先前描述的 α-乙酰基-α-重氮甲磺酰胺用于与含叠氮化物的苯甲醛和丙炔胺的三组分反应。除了最初形成三唑核外，反应在室温下以未催化的方式进一步进行，并在分子内叠氮化物-炔烃点击反应后产生结构有趣的新型双三唑。
• Oxidative Control of Photoinduced Cascade Electrocyclizations in Aromatic Azido Imines to Access Complex Fused Imidazoles or Pyrazoles
  作者：D. Sai Reddy、Ivan M. Novitskiy、Anastasia A. Beloglazkina、Andrei G. Kutateladze

  DOI：10.1021/acs.orglett.4c00361

  日期：2024.4.5

  Photoinduced cascade of two 6π-electron six- and five-center electrocyclizations in aromatic azido imines is oxidatively controlled to yield complex fused benzimidazoles or indazoles. Formation of benzimidazoles occurs via an unprecedented carbon-to-nitrogen o-iminoaryl 1,2-shift.

  芳香族叠氮亚胺中两个 6π 电子六中心和五中心电环化的光诱导级联受到氧化控制，产生复杂的稠合苯并咪唑或吲唑。苯并咪唑的形成是通过前所未有的碳氮邻亚氨基芳基 1,2-转变而发生的。