(5-hydroxynaphtho[1,2-b]furan-3-yl)-phenylmethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (5-hydroxynaphtho[1,2-b]furan-3-yl)-phenylmethanone
• 英文别名: 3-benzoylnaphtho[1,2-b]furan-5-ol；(5-Hydroxynaphtho[1,2-b]furan-3-yl)(phenyl)methanone；(5-hydroxybenzo[g][1]benzofuran-3-yl)-phenylmethanone
• 化学式: C₁₉H₁₂O₃
• 分子量: 288.302
• InChiKey: AZPQSBNSJXEOHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-hydroxynaphtho[1,2-b]furan-3-yl)-phenylmethanone 、 1,1-双(4-甲氧基苯基)-2-丙炔-1-醇 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， 反应 4.0h， 以52.4%的产率得到(6,6-bis(4-methoxyphenyl)-6H-benzo[h]furo[3,2-f ]chromen-3-yl)(phenyl)-methanone
  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：

  3 - （二甲氨基）- 1 -苯基 -2-丙烯-1-酮 以 乙醇 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 (5-hydroxynaphtho[1,2-b]furan-3-yl)-phenylmethanone
  参考文献：
  名称：

  烯胺在杂环合成中的合成：3-苯胺基-1-取代-2-丙烯-1-酮的合成和化学反应性

  摘要：

  3-苯胺基烯酮3a，b由相应的3-二苯甲基-氨基丙烯酮制备。的反应性3A，3B报告朝向各种碳和氮亲核试剂，以及萘醌的。

  DOI：

  10.1002/jhet.5570420414

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.
• Enaminones in heterocyclic synthesis: Synthesis and chemical reactivity of 3-anilino-1-substituted-2-propene-1- one
  作者：Balkis Al-Saleh、Morsy Ahmed El-Apasery、Rasha Safwat Abdel-Aziz、Mohamed Hilmy Elnagdi

  DOI：10.1002/jhet.5570420414

  日期：2005.5

  The 3-anilinoenones 3a,b were prepared from the corresponding 3-dimemyl-aminopropenones. The reactivity of 3a,b towards a variety of carbon and nitrogen nucleophiles as well as naphthoquinones is reported.

  3-苯胺基烯酮3a，b由相应的3-二苯甲基-氨基丙烯酮制备。的反应性3A，3B报告朝向各种碳和氮亲核试剂，以及萘醌的。