1-(4-methoxyphenyl)-4-(4'-nitrophenyl)-1,3-butadiene | 51079-92-6

• 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: 1-(4-methoxyphenyl)-4-(4'-nitrophenyl)-1,3-butadiene
• 英文别名: 1-(4-nitrophenyl)-4-(4-methoxyphenyl)-1,3-butadiene；4'-methoxy-4''-nitro-1,4-diphenyl-1,3-butadiene；1-Methoxy-4-[4-(4-nitrophenyl)buta-1,3-dien-1-yl]benzene；1-[4-(4-methoxyphenyl)buta-1,3-dienyl]-4-nitrobenzene
• CAS: 51079-92-6
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: FKRMOZCOCAOFKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-4-(4'-nitrophenyl)-1,3-butadiene 在 palladium on activated charcoal 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以70%的产率得到1-(4-methoxyphenyl)-4-(4'-aminophenyl)butane
  参考文献：
  名称：

  Correspondence between Molecular Functionality and Crystal Structures. Supramolecular Chemistry of a Family of Homologated Aminophenols

  摘要：

  The crystal structures and packing features of a family of 13 aminophenols, or supraminols, are analyzed and correlated. These compounds are divided into three groups: (a) compounds 1-5 with methylene spacers of the general type HO-C6H4-(CH2)(n)-C6H4-NH2 (n = 1 to 5) and both OH and NH2 in a para position; (b) compounds 1 a, 2a, 2b, 2c, and 3a in which one or more of the methylene linkers in 1 to 3 are exchanged with an S-atom; and (c) compounds 2d, 1b, and 6a prepared with considerations of crystal engineering and where the crystal structures may be anticipated on the basis of structures 1-5, 1 a, 2a, 2b, 2c, and 3a. These 13 aminols can be described in terms of three major supramolecular synthons based on hydrogen bonding between OH and NH2 groups: the tetrameric loop or square motif, the infinite N(H)O chain, and the beta-As sheet. These three synthons are not completely independent of each other but interrelate, with the structures tending toward the more stable beta-As sheet in some cases. Compounds 1-5 show an alternation in melting points, and compounds with n = even exhibit systematically higher melting points compared to those with n = odd. The alternating melting points are reflected in, and explained by, the alternation in the crystal structures. The n = odd structures tend toward the beta-As sheet as n increases and can be considered as a variable series whereas for n = even, the beta-As sheet is invariably formed constituting a fixed series. Substitution of a methylene group by an isosteric S-atom may causes a change in the crystal structure. These observations are rationalized in terms of geometrical and chemical effects of the functional groups. This study shows that even for compounds with complex crystal structures the packing may be reasonably anticipated provided a sufficient number of examples are available.

  DOI：

  10.1021/ja037227p
• 作为产物：
  描述：

  在 三聚氯氰 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以82%的产率得到1-(4-methoxyphenyl)-4-(4'-nitrophenyl)-1,3-butadiene
  参考文献：
  名称：

  Cyanuric chloride–dimethylformamide mediated cleavage of cyclopropylcarbinols-synthesis of phenolic antioxidant and construction of a new vinylcyclopropane skeleton

  摘要：

  DOI：

  10.1016/j.tetlet.2014.07.053

文献信息

• Nonlinear optical properties of diaromatic stilbene, butadiene and thiophene derivatives
  作者：Esa Kukkonen、Elmeri Lahtinen、Pasi Myllyperkiö、Matti Haukka、Jari Konu

  DOI：10.1039/d1nj00456e

  日期：——

  2-chloro-3,4-dimethoxy-4′-nitrostilbene derivative 1a to afford two polymorphs of tetra-aryl cyclobutane 4. The stilbene congeners 2-chloro-3,4-dimethoxy-4′-nitrostilbene (1a·non-centro), 5-bromo-2-hydroxy-3-nitro-4′-nitrostilbene (1b) and 4-dimethylamino-4′-nitrostilbene (1e), as well as 4′-fluoro-4′′-nitro-1,4-diphenyl-1,3-butadiene (2a) present the ideal, non-centrosymmetric arrangement of the chromophores

  通过霍纳-沃兹沃思-埃蒙斯方法制备了一系列高极性二苯乙烯（1a-e），二苯基丁二烯（2a-c）和苯基乙烯基噻吩（3a-c）衍生物，目的是生产新型有效的材料用于二次谐波（SHG）在固态。化合物1-3的单晶X射线结构显示了广泛的多态性和2-氯-3,4-二甲氧基-4'-亚硝基二苯乙烯衍生物1a的特殊光二聚化，从而得到了四芳基环丁烷4的两个多晶型物。二苯乙烯同类物2-氯-3,4-二甲氧基-4'-硝基nitro（1a ·非中心），5-溴-2-羟基-3-硝基-4'-硝基sti（1b）和4-二甲基氨基-4'-亚硝基苯乙烯（1e）以及4'-氟-4''-硝基-1,4-二苯基-1,3-丁二烯（2a）是理想的非中心对称排列非线性光学（NLO）活性的发色团的结构。化合物1b和2a的二次谐波产生强度相对较低（分别为尿素参照的0.04和0.18倍），而二苯乙烯多晶型物1a ·非中心的NLO活性超过尿素的32倍。此外，
• One-Pot Synthesis of 1,4-Diarylnaphthalenes via a Wittig-Horner Reaction/[4+2] Cycloaddition/Dehydrogenation Sequence
  作者：Yanguang Wang、Zhengbo Chen、Wangge Shou

  DOI：10.1055/s-0028-1083356

  日期：2009.4

  A one-pot synthesis of 1,4-diarylnaphthalenes from cinnamaldehydes, dimethyl benzylphosphonates, and benzenediazonium-2-carboxylate is described. The tandem process involves the Wittig-Horner reaction of the cinnamaldehyde with the benzylphosphonate, [4+2] cycloaddition of the thus-formed diene with benzyne, and subsequent dehydrogenation. The procedure is general and efficient and the substrates are

  描述了由肉桂醛，二甲基苄基膦酸酯和苯重氮-2-羧酸酯一锅法合成1,4-二芳基萘。串联过程涉及肉桂醛与苄基膦酸酯的Wittig-Horner反应，由此形成的二烯与苯炔的[4 + 2]环加成以及随后的脱氢。该过程是通用且有效的，并且衬底容易获得。 二苯基萘-串联反应-Wittig-Horner反应-环加成反应-苯并
• Influence of imidazolium ionic liquids on fluorescence of push-pull diphenylbutadienes
  作者：Anuji K. Vasu、Jagadish Katla、Naved I. Malek、Sriram Kanvah

  DOI：10.1016/j.jphotochem.2016.01.015

  日期：2016.5

  in ethanol. Excitation dependent emission studies of fluorophores in ionic liquids show distinct emission signals due to the locally excited and the charge transfer states revealing the existence of two species. Time resolved experiments show single exponential decay in organic solvents and bi-exponential decay in ionic liquids media,an indication of interaction of fluorophores with different microenvironments

  已经合成了一系列供体-受体取代的二苯基丁二烯，并研究了它们在有机溶剂和咪唑鎓离子液体介质中的荧光性质。取代的二苯丁二烯由于分子内电荷转移，在极性溶剂和离子液体中显示出显着的溶剂变色发光。有趣的是，含有甲氧基供体和硝基受体的二苯基丁二烯在乙醇中表现出激发依赖性的发射行为。离子液体中荧光团的激发依赖性发射研究表明，由于局部激发，电荷转移状态揭示了两种物质的存在，从而产生了不同的发射信号。时间分辨实验表明，有机溶剂中的单指数衰减和离子液体介质中的双指数衰减，
• Correspondence between Molecular Functionality and Crystal Structures. Supramolecular Chemistry of a Family of Homologated Aminophenols
  作者：Venu R. Vangala、Balakrishna R. Bhogala、Archan Dey、Gautam R. Desiraju、Charlotte K. Broder、Philip S. Smith、Raju Mondal、Judith A. K. Howard、Chick C. Wilson

  DOI：10.1021/ja037227p

  日期：2003.11.1

  The crystal structures and packing features of a family of 13 aminophenols, or supraminols, are analyzed and correlated. These compounds are divided into three groups: (a) compounds 1-5 with methylene spacers of the general type HO-C6H4-(CH2)(n)-C6H4-NH2 (n = 1 to 5) and both OH and NH2 in a para position; (b) compounds 1 a, 2a, 2b, 2c, and 3a in which one or more of the methylene linkers in 1 to 3 are exchanged with an S-atom; and (c) compounds 2d, 1b, and 6a prepared with considerations of crystal engineering and where the crystal structures may be anticipated on the basis of structures 1-5, 1 a, 2a, 2b, 2c, and 3a. These 13 aminols can be described in terms of three major supramolecular synthons based on hydrogen bonding between OH and NH2 groups: the tetrameric loop or square motif, the infinite N(H)O chain, and the beta-As sheet. These three synthons are not completely independent of each other but interrelate, with the structures tending toward the more stable beta-As sheet in some cases. Compounds 1-5 show an alternation in melting points, and compounds with n = even exhibit systematically higher melting points compared to those with n = odd. The alternating melting points are reflected in, and explained by, the alternation in the crystal structures. The n = odd structures tend toward the beta-As sheet as n increases and can be considered as a variable series whereas for n = even, the beta-As sheet is invariably formed constituting a fixed series. Substitution of a methylene group by an isosteric S-atom may causes a change in the crystal structure. These observations are rationalized in terms of geometrical and chemical effects of the functional groups. This study shows that even for compounds with complex crystal structures the packing may be reasonably anticipated provided a sufficient number of examples are available.
• Cyanuric chloride–dimethylformamide mediated cleavage of cyclopropylcarbinols-synthesis of phenolic antioxidant and construction of a new vinylcyclopropane skeleton
  作者：Sagar Khan、Sanchita Roy、Rimi Roy、Avishek Ghatak、Amit Pramanik、Sanjay Bhar

  DOI：10.1016/j.tetlet.2014.07.053

  日期：2014.9