3,3-bis(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-enone | 1616843-59-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3,3-bis(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-enone
• 英文别名: 1,1-bis(4-methoxyphenyl)-3-(4-methylphenyl)prop-2-enone
• CAS: 1616843-59-4
• 化学式: C₂₄H₂₂O₃
• 分子量: 358.437
• InChiKey: IFJCZZKPAPWIDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4,4'-二甲氧基二苯甲酮 、 4-甲苯基乙炔 在 正丁基锂 、 4-甲基苯磺酸吡啶 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 6.5h， 生成 3,3-bis(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-enone
  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

• The first structural and spectroscopic characterisation of a ring-opened form of a 2H-naphtho[1,2-b]pyran: a novel photomerocyanine
  作者：Stuart Aiken、Kathryn Booth、Christopher D. Gabbutt、B. Mark Heron、Craig R. Rice、Azzam Charaf-Eddin、Denis Jacquemin

  DOI：10.1039/c4cc03435j

  日期：——

  Heating 4-methoxy-1-naphthol with a 1,1-diarylprop-2-yn-1-ol gave the 2,2-diaryl-6-methoxy-2H-naphtho[1,2-b]pyran together with the novel merocyanine, (E)-2-[3',3'-bis(aryl)allylidene]-4-methoxynaphthalen-1(2H)-one. Brief UV-irradiation of the pyran favoured the formation of the (Z)-merocyanine with longer irradiation and/or acidic conditions favouring the (E)-isomer.

  将4-甲氧基-1-萘酚与1,1-二芳基丙-2-yn-1-醇加热，得到2,2-二芳基-6-甲氧基-2H-萘并[1,2-b]吡喃和新型色菁，（E）-2- [3'，3'-双（芳基）亚烷基] -4-甲氧基萘-1（2H）-一个。吡喃的短时紫外线辐照有利于形成具有更长辐照和/或酸性条件（有利于（E）-异构体）的（Z）-花青。