3,3-Bis(4-methoxyphenyl)[3H]naphtho[2,1-b]pyran | 28656-26-0

• 物质功能分类: 化学试剂 - 有机试剂 - 肼
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3,3-Bis(4-methoxyphenyl)[3H]naphtho[2,1-b]pyran
• 英文别名: 3,3-Bis(4-methoxyphenyl)benzo[f]chromene
• CAS: 28656-26-0
• 化学式: C₂₇H₂₂O₃
• 分子量: 394.47
• InChiKey: RPETUZOFZUKMCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-Bis(4-methoxyphenyl)[3H]naphtho[2,1-b]pyran 在 18-冠醚-6 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 9.0h， 以80%的产率得到2-(bis(4-methoxyphenyl)methyl)naphtho[2,1-b]furan
  参考文献：
  名称：

  钯和相转移催化促进的Pyran系统的碱介导的环收缩。

  摘要：

  描述了对模型3H-萘并[2,1-b]吡喃的环收缩的研究，以阐明和优化萘并吡喃的环收缩。据报道，有两种有效的碱介导的方案以通常良好的产率获得多个萘并呋喃，萘并呋喃和苯并稠合的吲哚。此外，提出了一种通过铃木偶联环收缩方法选择性制备（杂）芳基取代的萘呋喃的方案。据报道，另一种方案允许在溴取代的萘并吡喃上进行铃木交叉偶联反应而无环收缩副反应。

  DOI：

  10.1021/acs.joc.9b02901
• 作为产物：
  描述：

  4,4'-二甲氧基二苯甲酮 在 aluminum oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 5.75h， 生成 3,3-Bis(4-methoxyphenyl)[3H]naphtho[2,1-b]pyran
  参考文献：
  名称：

  光致变色萘并吡喃的合成观察

  摘要：

  1-萘酚与 1,1-diarylprop-2-yn-1-ols 5a,b 在氧化铝催化下通过两种途径反应得到光致变色的萘并 [1,2-b] 吡喃 6a,b 和丙烯酰-enenaphthalenones 7a,b，一类新的部花青染料的代表。使用 2-methyl-1-naphthol，可抑制光致变色；唯一的产品是部花青 7c,d。2-萘酚与 5a,b 的环缩合反应效率更高，得到萘并 [2, 1 b] 吡喃 14a,b。1-溴-或1-（4-甲氧基苯基）-2-萘酚不会抑制吡喃的形成；与 5a,b 的反应仅导致 C-1 取代基的排出。在 1-甲基-2-萘酚与 5a 反应生成苯并 [e] 茚满酮 17 的过程中出现了另一种途径，其组成由 X 射线晶体学确定。1,3的反应，3-三芳基丙炔醇19a、b与1-萘酚一起提供萘并吡喃20和部花青21，而异构吡喃23由2-萘酚有效地产生。部花青 7a 和 21a

  DOI：

  10.1002/ejoc.200390176

文献信息

• Synthesis and Photochromism of Novel Pyridyl-Substituted Naphthopyrans
  作者：Orlando D. C. C. de Azevedo、Paul I. P. Elliott、Christopher D. Gabbutt、B. Mark Heron、Kyle J. Lord、Christopher Pullen

  DOI：10.1021/acs.joc.0c01296

  日期：2020.8.21

  Multitarget synthetic strategies to access novel photochromic 3H-naphtho[2,1-b]pyrans decorated with pyridyl units are described. The new pyridyl-substituted 3H-naphtho[2,1-b]pyrans display good photochromic properties with reversible generation of photomerocyanines, which exhibit mainly orange/red hues. Photochromic parameters including photocolorability and persistence of color vary tremendously

  描述了多目标合成策略，以访问新型的吡啶基单元修饰的光致变色3 H-萘[ 2,1- b ]吡喃。新的吡啶基取代的3 H-萘[ 2,1 - b ]吡喃具有良好的光致变色特性，可逆生成的光金属花青素主要表现为橙色/红色。光致变色参数（包括光致变色性和颜色的持久性）在萘并吡喃核的结构修饰上有很大差异。
• Tuning the color switching of naphthopyrans via the control of polymeric architectures
  作者：Wilasinee Sriprom、Marjorie Néel、Christopher D. Gabbutt、B. Mark Heron、Sébastien Perrier

  DOI：10.1039/b617865k

  日期：——

  A range of polymerisable photochromic naphthopyrans were prepared via the synthesis of an acrylate moiety on either the naphthalene ring (R) and/or the di-aryl (Ar) rings on the 3-position of the naphthopyran. The monomers obtained (NA) were copolymerised with methyl methacrylate (MMA) and methyl acrylate (MA) by the RAFT (reversible addition fragmentation chain transfer) process in order to control the structure of the polymeric chains and accurately control the number of photochromic molecules per chain. Films were prepared with the synthesized photochromic polymers and their photochromic properties were assessed. We found that the fading rate of the photochromic dye was slower in a matrix of PMMA (higher Tg) than in a matrix of PMA (lower Tg). By producing block copolymers of PMMA-b-poly(MA-co-NA), the fading rate was increased, and the production of PS-b-poly(MA-co-NA) further enhanced the speed of switching, as phase separation occurred between the poly(MA-co-NA) block and the PS block. This study presents an example of tuning the photochromic properties of a dye via variation of the architecture of its polymeric support.

  一系列可聚合的光致变色萘吡喃通过在萘环（R）和/或二芳基（Ar）环的3位上合成丙烯酸酯基团来制备。获得的单体（NA）通过RAFT（可逆加成断裂链转移）过程与甲基丙烯酸甲酯（MMA）和丙烯酸甲酯（MA）共聚，以控制聚合物链的结构并精确控制每条链上的光致变色分子数量。制备了合成的光致变色聚合物薄膜并评估了它们的光致变色性能。我们发现，光致变色染料在PMMA（高Tg）基质中的褪色速率比在PMA（低Tg）基质中慢。通过制备PMMA-b-聚（MA-co-NA）嵌段共聚物，褪色速率增加，而制备PS-b-聚（MA-co-NA）进一步提高了开关速度，因为聚（MA-co-NA）嵌段和PS嵌段之间发生了相分离。这项研究展示了一个通过改变染料聚合物支撑结构的实例来调谐光致变色性能。
• Photochromic naphthopyran compounds
  申请人：Pilkington PLC

  公开号：US05623005A1

  公开（公告）日：1997-04-22

  A naphthopyran compound of general formula (I) ##STR1## wherein R.sub.1 represents a group of the formula --NR.sub.2 R.sub.3 wherein each of R.sub.2 and R.sub.3, which may be the same or different, independently represents an alkyl group, or a carbocyclic or heterocyclic group, or R.sub.2 and R.sub.3 taken together with the nitrogen atom to which they are attached represent a heterocyclic ring having one or more hetero atoms and which may optionally carry at least one substituent selected from alkyl, aryl, or heteroaryl groups; each of R.sub.4 and R.sub.5, which may be the same or different, independently represents an alkyl, alkenyl, carbocyclic or heterocyclic group, or R.sub.4 and R.sub.5 taken together with the carbon atom to which they are attached form a carboxylcyclic ring or a heterocyclic ring; and R.sub.6 represents a hydrogen atom or a substituent selected from alkyl, alkoxy, aryl, aryloxy, heteroaryl, halogen, a group of formula R.sub.1 as defined above, azo, imino, amide, carboxylate, ester, cyano, trifluoromethyl or nitro, and in addition R.sub.6 may represent a carbocyclic or heterocyclic ring fused to ring A. The naphthopyran compounds of the invention are useful as photochromic materials in lenses, e.g. sunglasses, and photochromic transparencies for cars and aircraft. The invention also provides, as new intermediate compounds, amine-substituted chloro-naphthols and amine-substituted naphthols.

  通用式(I)的萘吡喃化合物##STR1##其中R.sub.1代表式--NR.sub.2 R.sub.3的基团，其中R.sub.2和R.sub.3分别表示独立的烷基基团，或者是碳环或杂环基团，或者R.sub.2和R.sub.3与它们连接的氮原子一起表示具有一个或多个杂原子的杂环环，可以选择地携带来自烷基、芳基或杂芳基团中至少一个取代基；R.sub.4和R.sub.5，可以相同也可以不同，分别表示独立的烷基、烯基、碳环或杂环基团，或者R.sub.4和R.sub.5与它们连接的碳原子一起形成一个羧环或杂环环；R.sub.6表示氢原子或者从烷基、烷氧基、芳基、芳氧基、杂芳基、卤素、上述所定义的R.sub.1的基团、偶氮、亚胺、酰胺、羧酸酯、酯、氰基、三氟甲基或硝基中选择的取代基，并且此外R.sub.6可以表示与环A融合的碳环或杂环环。本发明的萘吡喃化合物可用作镜片中的光致变色材料，例如太阳镜，以及汽车和飞机的光致变色透明材料。本发明还提供了作为新中间体化合物的胺取代氯萘酚和胺取代萘酚。
• Facile One-Pot Synthesis of Photochromic Pyrans
  作者：Weili Zhao、Erick M. Carreira

  DOI：10.1021/ol035599x

  日期：2003.10.1

  [reaction: see text]. Photochromic pyrans, including [3H]naphtho[2,1-b]pyrans, [2H]naphtho[1,2-b]pyrans, indeno-fused naphtho[1,2-b]pyrans, and heteroannulated pyrans, were synthesized in excellent yields through a facile one-pot procedure by reaction of propargyl alcohol and naphthol or phenol derivatives in the presence of 5 mol % PPTS and 2 equiv of (MeO)3CH. Symmetrical and nonsymmetrical bispyrans

  [反应：请参见文字]。合成了包括[3H]萘[2,1-b]吡喃，[2H]萘[1,2-b]吡喃，茚并稠合的萘[1,2-b]吡喃和异环吡喃的光致变色吡喃。在5 mol％PPTS和2当量（MeO）3CH存在下，通过炔丙醇与萘酚或苯酚衍生物反应，通过简便的一锅法获得优异的收率。对称和非对称双吡喃也可以使用该方案制备。
• Photochromic compounds
  申请人：Pilkington PLC

  公开号：US05520853A1

  公开（公告）日：1996-05-28

  A naphthopyran compound of general formula (I) ##STR1## wherein R.sub.1 represents an alkyl group or an aryl group; each of R.sub.4 and R.sub.5, which may be the same or different, independently represents an alkyl, alkenyl, carbocyclic or heterocyclic group, or R.sub.4 and R.sub.5 taken together with the carbon atom to which they are attached form a carbocyclic ring or a heterocyclic ring; and R.sub.6 represents a hydrogen atom or a substituent selected from alkyl, alkoxy, aryl, aryloxy, heteroaryl, halogen, amino, substituted amino, azo, imino, amide, carboxylate, ester, cyano, trifluromethyl or nitro, and in addition R.sub.6 may represent a carbocyciic or heterocyclic ring fused to ring A. The naphthopyran compounds of the invention are useful as photochromic materials in lenses, e.g. sunglasses, and photochromic transparencies for cars and aircraft.

  通用公式（I）的萘吡喃化合物##STR1##其中R.sub.1代表烷基或芳基；R.sub.4和R.sub.5中的每一个，可以相同也可以不同，独立地代表烷基、烯基、碳环或杂环基，或者R.sub.4和R.sub.5与它们连接的碳原子一起形成碳环或杂环；R.sub.6代表氢原子或从烷基、烷氧基、芳基、芳氧基、杂芳基、卤素、氨基、取代氨基、偶氮基、亚胺基、酰胺基、羧酸酯、酯基、氰基、三氟甲基或硝基中选择的取代基，此外R.sub.6还可以表示与环A融合的碳环或杂环。本发明的萘吡喃化合物可用作镜片中的光致变色材料，例如太阳镜，以及汽车和飞机的光致变色透明材料。