2,3-dihydroxy-1-nitrosonaphthalene | 145097-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dihydroxy-1-nitrosonaphthalene
• 英文别名: 1-nitozo-2,3-dihydroxynaphthalene；1-Nitroso-2,3-naphthalenediol；1-nitrosonaphthalene-2,3-diol
• CAS: 145097-43-4
• 化学式: C₁₀H₇NO₃
• 分子量: 189.17
• InChiKey: UQULNQPIVBWYMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dihydroxy-1-nitrosonaphthalene 在 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,1,3-trimethyl-5'-(1,4,7,10-tetraoxa-13-aza-13-cyclopentadecyl)pentylcarboxy-3'H-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]
  参考文献：
  名称：

  含冠的螺恶嗪和螺吡喃

  摘要：

  开发了在两个不同位置（5' 和 9'）包含 aza-15-crown-5 片段的新型螺萘并恶嗪的合成方法。这些化合物的光谱和光化学性质表明，两种竞争性络合过程与碱土金属或稀土金属阳离子的效率和选择性不同。金属阳离子相对于染料的部花青形式的供体氧原子占据冠醚腔中的最佳位置，因此与分子间相互作用的情况相比，可以更强烈地影响其光谱和光化学性质。

  DOI：

  10.1007/bf02494754
• 作为产物：
  描述：

  2,3-二羟基萘 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 2,3-dihydroxy-1-nitrosonaphthalene
  参考文献：
  名称：

  The molecular design, synthesis and photochromic properties of spirooxazines containing a permanent azo (hydrazone) chromophore

  摘要：

  A range of molecular modelling techniques has been applied to predict optimized geometrical conformations and energies of the ring-closed oxazine form and ring-opened merocyanine forms of three azospirooxazines. A comparison of the relative stabilities of the possible isomers of the merocyanines was carried out by applying molecular mechanics (augmented MM2), while the prediction of the potential for photochromic behaviour was made by comparison of the heats of formation calculated by AMI. Synthetic routes were explored and as a result two azospirooxazines were isolated, one of which showed interesting and unusual photochromic behaviour. The instability of this compound towards purification by chromatography was investigated. The decomposition product was isolated and characterized with the aid of single crystal x-ray crystallography. The correlation between predicted and observed photochromic behaviour is discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.02.017

文献信息

• Crown-containing spirooxazines and spiropyrans
  作者：O. A. Fedorova、S. P. Gromov、Yu. P. Strokach、Yu. V. Pershina、S. A. Sergeev、V. A. Barachevskii、G. Pepe、A. Samat、R. Guglielmetti、M. A. Alfimov

  DOI：10.1007/bf02494754

  日期：1999.10

  Methods for the synthesis of new spironaphthooxazines containing an aza-15-crown-5 fragment in two different positions (5′ and 9′) were developed. The spectral and photochemical properties of these compounds suggest that two competitive complexation processes occur with alkaline-earth or rare-earth metal cations differing in efficiency and selectivity. A metal cation occupies the optimum position in

  开发了在两个不同位置（5' 和 9'）包含 aza-15-crown-5 片段的新型螺萘并恶嗪的合成方法。这些化合物的光谱和光化学性质表明，两种竞争性络合过程与碱土金属或稀土金属阳离子的效率和选择性不同。金属阳离子相对于染料的部花青形式的供体氧原子占据冠醚腔中的最佳位置，因此与分子间相互作用的情况相比，可以更强烈地影响其光谱和光化学性质。
• Highly efficient green synthesis of the photochromic spironaphthoxazines using an eco-friendly choline hydroxide catalyst
  作者：Shailesh N. Vajekar、Ganapati S. Shankarling

  DOI：10.1080/00397911.2019.1694690

  日期：2020.2.1

  Abstract A greener route for the synthesis of the photochromic spironaphthoxazines employing a highly efficient, biodegradable and recyclable choline hydroxide catalyst in an aqueous medium has been described. This methodology offers diverse advantages such as mild reaction conditions, short reaction time (1 h), excellent yields (up to 91%), and operational simplicity that make it a useful and attractive

  摘要描述了一种在水性介质中使用高效、可生物降解和可回收的氢氧化胆碱催化剂合成光致变色螺萘恶嗪的绿色途径。该方法具有多种优势，例如反应条件温和、反应时间短（1 小时）、优异的产率（高达 91%）和操作简单，使其成为合成螺萘恶嗪的有用且有吸引力的选择。氢氧化胆碱显示出优异的催化性能，直至五次循环均未显着降低活性。通过1H NMR谱和熔点推断合成的螺萘恶嗪的结构。图形概要
• JPH04208289A
  申请人：——

  公开号：JPH04208289A

  公开（公告）日：1992-07-29
• MECHANOCHROMIC COATING COMPOSITION
  申请人：Chopra Anu

  公开号：US20130269445A1

  公开（公告）日：2013-10-17

  A mechanochromic coating composition is disclosed comprising a polymeric network incorporating a plurality of ring-opening mechanophores each bound at two positions thereof within said polymeric network.
• POLYMER COMPOSITIONS CONTAINING MECHANOCHROMIC POLYMERS
  申请人：PPG INDUSTRIES OHIO, INC.

  公开号：US20130274412A1

  公开（公告）日：2013-10-17

  The present invention relates to a polymer composition that includes a polymer having at least one polymer segment represented by the following Formula (I), With reference to Formula (I): M independently for each w is a residue of a monomer; φ is a residue of a mechanochromic compound having at least two reactive groups that are each independently bonded to one monomer residue M; w, independently for each z, is an integer of at least 1; and z is an integer of at least 2. The mechanochromic compound is selected from at least one of the following, (a) a spirooxazine compound represented by the following Formula (II), and (b) an indenonaphthopyran represented by the following Formula (III),