(E,E)-4-methyl-4'-(4''-methylstyryl)stilbene | 58358-54-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E)-4-methyl-4'-(4''-methylstyryl)stilbene
• 英文别名: (E,E)-1,4-bis[p-methylstyryl]benzene；1,4-bis((E)-4-methylstyryl)benzene；1,4-bis[(E)-4-methylstyryl]benzene；1,4-Bis(4-methylstyryl)benzene；p-MSB；1,4-bis-(4-methyl-trans-styryl)-benzene；1,4-bis[(E)-2-(4-methylphenyl)ethenyl]benzene
• CAS: 58358-54-6
• 化学式: C₂₄H₂₂
• 分子量: 310.439
• InChiKey: BCASZEAAHJEDAL-PHEQNACWSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  471.9±40.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E,E)-4-methyl-4'-(4''-methylstyryl)stilbene 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 1.5h， 生成 (E,E)-1,4-bis[4-(acetylsulfanylmethyl)styryl]benzene
  参考文献：
  名称：

  Fabrication of Steady Junctions Consisting of α,ω-Bis(thioacetate) Oligo(p-phenylene vinylene)s in Nanogap Electrodes

  摘要：

  For obtaining molecular devices using metal-molecule-metal junctions, it is necessary to fabricate a steady conductive bridge-structure; that is stable chemical bonds need to be established from a single conductive molecule to two facing electrodes. In the present paper, we show that the steadiness of a conductive bridge-structure depends on the molecular structure of the bridge molecule for nanogap junctions using three types of modified oligo(phenylene vinylene)s (OPVs): alpha,omega-bis(thioacetate) oligo(phenylene vinylene) (OPV1), alpha,omega-bis(methylthioacetate) oligo(phenylene vinylene) (OPV2), and OPV2 consisting of ethoxy side chains (OPV3). We examined the change in resistance between the molecule-bridged junction and a bare junction in each of the experimental Au-OPV-Au junctions to confirm whether molecules formed steady bridges. Herein, the outcomes of whether molecules formed steady bridges were defined in terms of three types of result; successful, possible and failure. We define the ratio of the number of successful junctions to the total number of experimental junctions as successful rate. A 60% successful rate for OPV3 was higher than for the other two molecules whose successful rates were estimated to be similar to 10%. We propose that conjugated molecules consisting of methylthioacetate termini and short alkoxy side chains are well suited for fabricating a steady conductive bridge-structure between two facing electrodes.

  DOI：

  10.1021/ja062561h
• 作为产物：
  描述：

  1,4-bis[2-bromo-1-(4-methylphenyl)ethyl]benzene 以 二乙二醇 为溶剂， 反应 6.0h， 生成 (E,E)-4-methyl-4'-(4''-methylstyryl)stilbene
  参考文献：
  名称：

  Vartanyan, S. A.; Araratyan, E. A.; Tovmasyan, D. L., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 290 - 292

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Stereoselective Synthesis of (E)-Stilbenes via Organozinc Reagents and Carbonyl Compounds
  作者：Jin-Xian Wang、Kehu Wang、Lianbiao Zhao、Hongxia Li、Ying Fu、Yulai Hu

  DOI：10.1002/adsc.200606016

  日期：——

  In the presence of a catalytic amount of PdCl2(PPh3)2 and a silylating agent, organozinc halides reacted with carbonyl compounds to give the corresponding (E)-stilbenes in good to excellent yields under mild conditions. The reaction mechanism is briefly discussed.

  在催化量的PdCl 2（PPh 3）2和甲硅烷基化剂的存在下，有机锌卤化物与羰基化合物反应，在温和的条件下以良好或优异的收率得到相应的（E）-芪。简要讨论了反应机理。
• Ruthenium-Sulfonamide-Catalyzed Direct Dehydrative Condensation of Benzylic C–H Bonds with Aromatic Aldehydes
  作者：Shin Takemoto、Eri Shibata、Mitsuaki Nakajima、Yoshihiro Yumoto、Mayuko Shimamoto、Hiroyuki Matsuzaka

  DOI：10.1021/jacs.6b08863

  日期：2016.11.16

  The first catalytic dehydrative condensation of the benzylic C-H bonds of toluene and p-xylene with aromatic aldehydes is reported herein. This protocol provides highly atom-economical access to stilbene and p-distyrylbenzene derivatives, whereby water is the sole byproduct. The reaction is based on the deprotonation-functionalization of benzylic C-H bonds through η6-complexation of the arenes, which

  本文报道了甲苯和对二甲苯的苄基 CH 键与芳香醛的第一次催化脱水缩合。该协议提供了对二苯乙烯和对二苯乙烯基苯衍生物的高度原子经济访问，其中水是唯一的副产品。该反应基于通过芳烃的 η6-络合实现苄基 CH 键的去质子化功能化，这是首次使用催化量的过渡金属活化剂实现的。该方法成功的关键是使用磺酰胺阴离子作为催化剂组分，这似乎不仅有助于苄基 CH 键的去质子化，而且还有助于通过亲电子甲苯磺酸亚胺中间体形成 CC 键。
• Photochemical Behavior of Some p-Styrylstilbenes and Related Compounds: Spectral Properties and Photoisomerization in Solution and in Solid State
  作者：Zhu Fengqiang、Jiro Motoyoshiya、Junji Nakamura、Yoshinori Nishii、Hiromu Aoyama

  DOI：10.1562/2006-01-17-ra-780

  日期：——

  nzene and a 4,4'-distyrylstilbene were investigated in solution and in the solid state. Some notable features of the absorption and fluorescence spectra due to the structures and the phases (solution or solid) were observed, especially the Stokes shifts. Interesting photochemical behaviors in solution and in the solid state were also found. While the (E,Z)-4-styrylstilbenes undergo a one-way photoisomerization

  研究了三种4-苯乙烯基苯乙烯，4,4'-双（P-甲基苯乙烯基）苯和4,4'-二苯乙烯基苯乙烯的光谱性质和Z，E-光异构化状态。观察到由于结构和相（溶液或固体）而引起的吸收光谱和荧光光谱的一些显着特征，尤其是斯托克斯位移。还发现了溶液和固态中有趣的光化学行为。尽管（E，Z）-4-苯乙烯基苯甲酸酯在溶液中以几乎相同的速率发生单向光异构化为其E，E异构体，但其固态量子产率随着末端芳香环上取代基尺寸的增加而降低。另一方面，4,4'-双（β-甲基苯乙烯基）苯在溶液中经历相互的光异构化，但其E Z-异构体以单向方式异构化为固态的E，E-异构体。此外，发现（Z，E，Z）-4,4'-苯乙烯基苯乙烯通过溶液中的E，E，Z-异构体和结晶E经历单向光异构化为E，E，E-异构体，E，Z-异构体为固态的E，E，E-异构体。
• Bistable Photoswitching in the Film of Fluorescent Photochromic Polymer:  Enhanced Fluorescence Emission and Its High Contrast Switching
  作者：Seon-Jeong Lim、Byeong-Kwan An、Soo Young Park

  DOI：10.1021/ma0504163

  日期：2005.7.26
• Drefahl; Ploetner, Chemische Berichte, 1958, vol. 91, p. 1274,1277
  作者：Drefahl、Ploetner

  DOI：——

  日期：——

表征谱图