1-azido-6-naphthol | 56548-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-azido-6-naphthol
• 英文别名: 5-azido-2-naphthol；5-Azidonaphthalen-2-ol
• CAS: 56548-16-4
• 化学式: C₁₀H₇N₃O
• 分子量: 185.185
• InChiKey: HDORCDWHNYMTAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-azido-6-naphthol 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 以89%的产率得到5-azido-1-nitroso-2-naphthol
  参考文献：
  名称：

  Synthesis and spectroscopic characterization of red-shifted spironaphthoxazine based optical switch probes

  摘要：

  Spironaphthoxazine (NISO) is an efficient optical switch probe that has applications in high contrast detection of Forster resonance energy transfer (FRET) using optical lock-in detection (OLID). NISO exists in two distinct states, spiro (SP) and merocyanine (MC), that can be independently controlled by using alternate irradiation with near ultraviolet and visible light. Unfortunately, the SP-state of NISO has an absorption centered at 350 nm, which may lead to phototoxic effects when manipulating the probe within a living cell. To overcome this problem we introduce new, red-shifted amino-substituted NISO probes compared to NISO that undergo an efficient SP to MC transition in response to irradiation by using 405-nm light, which is less damaging to living cells. This study details the synthesis of amino-substituted NISO and their N-hydroxysuccinimide ester and maleimide derivatives and their use in generating covalent attached protein conjugates. This study also presents a characterization of the spectroscopic and optical switching properties of these red-shifted NISO probe in solution. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.084
• 作为产物：
  描述：

  5-氨基-2-萘酚 在 盐酸 、 sodium azide 、 sodium nitrite 作用下， 以55%的产率得到1-azido-6-naphthol
  参考文献：
  名称：

  8,9-二氢苯并[g]哒嗪并[4,5-b]吲哚-7,10（11H）-二酮的合成及化学发光活性

  摘要：

  取代的和未取代的萘胺被转化为相应的三唑衍生物，并通过光环化将其转化为1 H-苯并[ g ]吲哚-2,3-二羧酸二甲酯。二酯与水合肼的反应得到相应的8，9-二氢苯并[ g ]-哒嗪并[4，5 - b ]吲哚-7，10 （11H）-二酮（5）。发现化合物5之一具有与鲁米诺相似的化学发光活性。

  DOI：

  10.1002/jhet.5570380313

文献信息

• Synthesis and chemiluminescent activity of 8,9-dihydrobenzo[g] pyridazino[4,5-b]indole-7,10(11H)-diones
  作者：Masateru Kurumi、Kenji Sasaki、Hiroko Takata、Taiji Nakayama

  DOI：10.1002/jhet.5570380313

  日期：2001.5

  corresponding triazole derivatives, which were converted to dimethyl 1H-benz[g]indole-2,3-dicarboxylates by photocyclization. The reaction of the diesters with hydrazine hydrate gave the corresponding 8,9-dihydrobenzo[g]-pyridazino[4,5-b]indole-7,10(11H)-diones (5). One of compounds 5 was found to have chemiluminescent activity similar to luminol.

  取代的和未取代的萘胺被转化为相应的三唑衍生物，并通过光环化将其转化为1 H-苯并[ g ]吲哚-2,3-二羧酸二甲酯。二酯与水合肼的反应得到相应的8，9-二氢苯并[ g ]-哒嗪并[4，5 - b ]吲哚-7，10 （11H）-二酮（5）。发现化合物5之一具有与鲁米诺相似的化学发光活性。
• Synthesis and spectroscopic characterization of red-shifted spironaphthoxazine based optical switch probes
  作者：Chutima Petchprayoon、Gerard Marriott

  DOI：10.1016/j.tetlet.2010.10.084

  日期：2010.12

  Spironaphthoxazine (NISO) is an efficient optical switch probe that has applications in high contrast detection of Forster resonance energy transfer (FRET) using optical lock-in detection (OLID). NISO exists in two distinct states, spiro (SP) and merocyanine (MC), that can be independently controlled by using alternate irradiation with near ultraviolet and visible light. Unfortunately, the SP-state of NISO has an absorption centered at 350 nm, which may lead to phototoxic effects when manipulating the probe within a living cell. To overcome this problem we introduce new, red-shifted amino-substituted NISO probes compared to NISO that undergo an efficient SP to MC transition in response to irradiation by using 405-nm light, which is less damaging to living cells. This study details the synthesis of amino-substituted NISO and their N-hydroxysuccinimide ester and maleimide derivatives and their use in generating covalent attached protein conjugates. This study also presents a characterization of the spectroscopic and optical switching properties of these red-shifted NISO probe in solution. (C) 2010 Elsevier Ltd. All rights reserved.