3-methacryloxymethyl-O-(N,N-dimethylcarbamoyl)-5-nitrosalicylaldehyde | 132221-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methacryloxymethyl-O-(N,N-dimethylcarbamoyl)-5-nitrosalicylaldehyde
• 英文别名: 3-methacryloxymethyl-2-O-(N,N-dimethylthiocarbamoyl)-5-nitrosalicylaldehyde；[2-(Dimethylcarbamothioyloxy)-3-formyl-5-nitrophenyl]methyl 2-methylprop-2-enoate
• CAS: 132221-47-7
• 化学式: C₁₅H₁₆N₂O₆S
• 分子量: 352.368
• InChiKey: HQSNQEOGYXHVAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-methacryloxymethyl-O-(N,N-dimethylcarbamoyl)-5-nitrosalicylaldehyde 在 sodium hydroxide 作用下， 以 甲醇 、 甲苯 、 丁酮 为溶剂， 生成 8-methacryloxymethyl-6-nitro-1',3',3'-trimethylspiro[2H-1-benzothiopyran-2,2'-indoline]
  参考文献：
  名称：

  Synthesis and Metastable Structure of New Photochromic Spiroindolinobenzothiopyrans

  摘要：

  我们制备出了具有甲基丙烯酰氧基甲基的光致变色螺吲哚啉基苯并噻喃，并根据光谱数据证明其彩色形式是一种齐聚物结构。

  DOI：

  10.1246/cl.1991.209
• 作为产物：
  描述：

  3-氯甲基-5-硝基水杨醛 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 3-methacryloxymethyl-O-(N,N-dimethylcarbamoyl)-5-nitrosalicylaldehyde
  参考文献：
  名称：

  Synthesis and Metastable Structure of New Photochromic Spiroindolinobenzothiopyrans

  摘要：

  我们制备出了具有甲基丙烯酰氧基甲基的光致变色螺吲哚啉基苯并噻喃，并根据光谱数据证明其彩色形式是一种齐聚物结构。

  DOI：

  10.1246/cl.1991.209

文献信息

• Synthesis and Metastable Structure of New Photochromic Spiroindolinobenzothiopyrans
  作者：Masafumi Hirano、Akira Miyashita、Hiroyuki Nohira

  DOI：10.1246/cl.1991.209

  日期：1991.2

  Photochromic spiroindolinobenzothiopyrans having a methacryloxymethyl group have been prepared and their colored forms were demonstrated to be a zwitterionic structure on the basis of the spectroscopic data.

  我们制备出了具有甲基丙烯酰氧基甲基的光致变色螺吲哚啉基苯并噻喃，并根据光谱数据证明其彩色形式是一种齐聚物结构。
• Crystal and Solution Structures of Photochromic Spirobenzothiopyran. First Full Characterization of the Meta-Stable Colored Species
  作者：Masafumi Hirano、Kohtaro Osakada、Hiroyuki Nohira、Akira Miyashita

  DOI：10.1021/jo011011t

  日期：2002.1.1

  Full elucidation for stable, colorless, and meta-stable colored structures of a new spirobenzothiopyran has been achieved both in the solid state and in a solution. 1',3',3'-Trimethyl-6-nitrospiro[(2H)-1-benzothiopyran-2,2'-indolinel with an ester group as a substituent at the 8-position of 1-sp shows photochromism. The blue-green colored species resulted from UV irradiation (365 nm) in one minute and spontaneously bleaches within one minute in acetone and methanol at 27 degreesC. UV exposure (365 nm) of 1-sp in methanol for 3 h at room temperature results in the growth of deep blue needlelike single crystals of the open form of spirobenzothiopyran, photomerocyanine 1-pmc, whose structures in the solid state and in solution were obtained unambiguously. The X-ray structural analysis of 1-pmc revealed the molecular structure of the zwitterionic photomerocyanine with s-trans,s-trans conformation. 1-pmc is soluble to polar solvents and thermally returns to 1-sp. In the DMSO solution, 1-pmc is found to return slowly to 1-sp (1-pmc gave only 18% of 1-sp for 30 min at 22 degreesC). The detailed NMR studies in DMSO-d(6) including COSY and NOE techniques as well as isotope labeling of the compound showed the structure with s-trans,s-cis conformation in a solution.