N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并噻唑类
• 英文名称: N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide
• 英文别名: N-(5-hydroxybenzo[e][1,3]benzothiazol-2-yl)acetamide
• 化学式: C₁₃H₁₀N₂O₂S
• 分子量: 258.301
• InChiKey: AINVYAFODYRAER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  90.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-双(4-甲氧基苯基)-2-丙炔-1-醇 、 N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide 在 4-甲基苯磺酸吡啶 、 原甲酸三甲酯 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 、
  参考文献：
  名称：

  5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes

  摘要：

  3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2'-binaphthothiazole]-1,1'-diol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.043
• 作为产物：
  描述：

  2-氨基萘并o[1,2-d][1,3]噻唑-5-醇 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide
  参考文献：
  名称：

  5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes

  摘要：

  3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2'-binaphthothiazole]-1,1'-diol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.043

文献信息

• 5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes
  作者：Stuart Aiken、Ben Allsopp、Kathryn Booth、Christopher D. Gabbutt、B. Mark Heron、Craig R. Rice

  DOI：10.1016/j.tet.2014.10.043

  日期：2014.12

  3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2'-binaphthothiazole]-1,1'-diol. (C) 2014 Elsevier Ltd. All rights reserved.