(E)-1-(4-bromophenyl)-2-(2-naphthyl)ethylene | 53034-14-3

• 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)-1-(4-bromophenyl)-2-(2-naphthyl)ethylene
• 英文别名: (E)-1-(p-bromophenyl)-2-(2-naphthyl)ethylene；(E)-2-[2-(4-bromophenyl)ethenyl]naphthalene；2-[2-(4-bromophenyl)ethenyl]naphthalene；trans-2-(4-bromostyryl)naphthalene；(E)-2-(4-bromostyryl)naphthalene；2-(4-bromostyryl)-naphthalene；2-[(E)-2-(4-bromophenyl)ethenyl]naphthalene
• CAS: 53034-14-3
• 化学式: C₁₈H₁₃Br
• 分子量: 309.205
• InChiKey: ZUVMZPGQHZUIMR-AATRIKPKSA-N

物化性质

• 熔点：
  192 °C
• 沸点：
  435.8±20.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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)-1-(4-bromophenyl)-2-(2-naphthyl)ethylene 在 碘 作用下， 以 甲苯 为溶剂， 以88%的产率得到2-溴苯并(c)菲
  参考文献：
  名称：

  端环氟化的[6]螺内酯的制备及理化性质

  摘要：

  第一个外消旋稳定的lic烯衍生物在末端环上氟化1,2,3,4-四氟[6] hel烯（6）和1,2,3,4,13,14,15,15,16-八氟[6] ic烯（15）是通过Wittig反应合成的，然后是氧化光环化反应，其总收率为6的41％和15的76％。与未取代的[6]螺旋烯相比，氟化螺旋烯的电子结构变化反映在UV-vis吸收，荧光激发和发射光谱最大值的微小变化中。循环伏安法显示，随着氟化作用的增加，HOMO-LUMO间隙适度减少。四氟[6] hel烯的比旋光度6发现对映异构体比未取代的[6]螺旋烯低约25％。外消旋化阻挡层的理论研究表明，随着氟化作用的增加，向高能量的合理转变。氟化的增加也显着影响晶格中的分子间相互作用。观察到的CH···F相互作用导致在两个氟化螺旋烯的晶体结构中形成一维分子链。

  DOI：

  10.1021/acs.joc.8b02870
• 作为产物：
  描述：

  对溴溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.33h， 生成 (E)-1-(4-bromophenyl)-2-(2-naphthyl)ethylene
  参考文献：
  名称：

  Fluorescence Enhancement of trans-4-Aminostilbene by N-Phenyl Substitutions:  The “Amino Conjugation Effect”

  摘要：

  The synthesis, structure, and photochemical behavior of the trans isomers of 4-(N-phenylamino)stilbene (1c), 4-(A methyl-N-phenylamino)stilbene (1d), 4-(NN-diphenylamino)stilbene (le), and 4-(N-(2,6dimethylphenyl)amino)stilbene (1f) are reported and compared to that of 4-aminostilbene (1a) and 4-N,N-dimethylaminostilbene (1b). Results for the corresponding 3-styrylpyridine (2) and 2-styrylnaphthalene analogues (3) are also included. The introduction of N-phenyl substituents to 4-aminostilbenes leads to a more planar ground-state geometry about the nitrogen atom, a red shift of the absorption and fluorescence spectra, and a less distorted structure with a larger charge-transfer character for the fluorescent excited state. Consequently, the N-phenyl derivatives 1c-e have low photoisomerization quantum yields and high fluorescence quantum yields at room temperature, in contrast to the behavior of la, 1b, and most unconstrained monosubstituted trans-stilbenes. The isomerization of 1c and 1d is a singlet-state process, whereas it is a triplet-state process for le, presumably due to a relatively higher singlet-state torsional barrier. The excited-state behavior of 1f resembles 1a and 1b instead of 1c-e as a consequence of the less planar amine geometry and weaker orbital interactions between the N-phenyl and the aminostilbene groups. Such an N-phenyl substituent effect is also found for 2 and 3 and thus appears to be general for stilbenoid systems. The nature of this effect can be described as an ''amino conjugation effect''.

  DOI：

  10.1021/ja016416+

文献信息

• Synthesis of stilbene analogues by one-pot oxidation-Wittig and oxidation-Wittig–Heck reaction
  作者：Akeel S. Saiyed、Krupa N. Patel、Bola V. Kamath、Ashutosh V. Bedekar

  DOI：10.1016/j.tetlet.2012.06.090

  日期：2012.8

  Synthesis of symmetrical (and unsymmetrical) stilbene derivatives is achieved by a combination of one-pot steps of Kornblum type oxidation of benzyl halide, its simultaneous in situ formation of phosphonium salt, and subsequently their Wittig reaction. In other variant it is oxidized to aldehyde, treated with ylide generated from phosphonium salt (CH3PPh3X) to give styrene, and subjected to Pd catalyzed

  对称（和不对称）二苯乙烯衍生物的合成是通过将一锅法的Kornblum型苄基卤化物氧化，同时同时原位形成phospho盐以及随后的Wittig反应相结合来实现的。在另一变体中，将其氧化成醛，用由salt盐（CH 3 PPh 3 X）产生的内鎓盐处理以得到苯乙烯，并与芳基卤化物进行Pd催化的Heck反应，以三步一锅法得到丁苯二酚。
• Direct Wittig Olefination of Alcohols
  作者：Qiang-Qiang Li、Zaher Shah、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.joc.7b02720

  日期：2018.1.5

  A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefination

  描述了在有氧条件下使用醇作为廉价且清洁的氧化剂，使用醇在碱性条件下使用无醇过渡醇取代烯烃的方法。与相应的醇相比，由于醛的挥发性和聚合和自氧化倾向，因此醛相对较难处理。维蒂希酸根易于氧化成醛，因此形成均烯烃化产物。首次通过同时原位生成乙叉和乙叉的策略，无需预先制备醛或乙叉醇就将醇直接转移到烯烃中。因此，实现了二醇的二/单可控烯烃化。这种合成实用的方法已用于克级合成的药物，如DMU-212和白藜芦醇。
• Palladium-catalyzed Mizoroki-Heck reactions in water using thermoresponsive polymer micelles
  作者：Noriyuki Suzuki、Taiga Takabe、Yoshiko Yamauchi、Shun Koyama、Rina Koike、Masahiro Rikukawa、Wei-Ting Liao、Wen-Sheng Peng、Fu-Yu Tsai

  DOI：10.1016/j.tet.2019.01.047

  日期：2019.3

  solution, enabling efficient extraction of the products from aqueous reaction mixture. In the presence of these copolymers, palladium complexes catalyzed the coupling reactions between aryl iodides and alkene compounds inside the hydrophobic micelle cores in water under relatively milder conditions. Extraction of the products from the aqueous solution of 2 or 9 was found to be efficient enough in comparison

  使用热响应性聚合物胶束在水中进行钯催化的Mizoroki-Heck反应。胶束是由热响应性嵌段共聚物生成的，该嵌段共聚物由聚（N-异丙基丙烯酰胺）（PNIPAAm）链段和亲水性链段组成，例如非离子聚（乙二醇）（PEG）（2）和阴离子聚（对苯乙烯磺酸钠）（PSSNa） ）（9）。这些共聚物在约200℃下显示出较低的临界溶液温度（LCST）行为。40–50°C，并显示出热刺激诱导的胶束形成和解离。共聚物在较高温度下在水溶液中形成胶束，在其中进行催化反应。在较低温度下，胶束解离形成澄清溶液，从而能够从水性反应混合物中高效提取产物。在这些共聚物的存在下，钯络合物在相对温和的条件下催化了疏水性胶束核心内的芳基碘化物与烯烃化合物之间的偶联反应。与常规的表面活性剂相比，发现从2或9的水溶液中提取产物是足够有效的。
• Catalytic Epoxidations with Pyridinebis(oxazoline)–Methyltrioxorhenium Complexes and Nitrogen‐Containing Catalyst Systems
  作者：Konstanze Kiersch、Yuehui Li、Kathrin Junge、Normen Szesni、Richard Fischer、Fritz E. Kühn、Matthias Beller

  DOI：10.1002/ejic.201200736

  日期：2012.12

  The epoxidation of olefins with methyltrioxorhenium (MTO) in the presence of various chiral oxazolines and pyridinebis(oxazoline) ligands as well as achiral N-ligands has been investigated. By applying 1-octene as a model system, reaction conditions were optimized, and high yields and good chemoselectivity (>90?

  已经研究了在各种手性恶唑啉和吡啶双（恶唑啉）配体以及非手性 N-配体存在下，烯烃与甲基三氧铼 (MTO) 的环氧化反应。以1-辛烯为模型体系，优化了反应条件，获得了高产率和良好的化学选择性（>90?
• Expeditious synthesis of helicenes using an improved protocol of photocyclodehydrogenation of stilbenes
  作者：Harish R. Talele、Anju R. Chaudhary、Parthiv R. Patel、Ashutosh V. Bedekar

  DOI：10.3998/ark.5550190.0012.902

  日期：——

  developed for photodehydrocyclization of stilbenes for the synthesis of phenanthrenes and helicenes. This procedure involves the use of THF as a scavenger of hydriodic acid produced during iodine mediated photodehydrocyclization. The use of THF is advantageous due to its higher boiling point, lower cost and easy availability as compared to propylene oxide. The method is applied to synthesize a number

  已开发出一种用于合成菲和螺旋烯的二苯乙烯光脱氢环化的改进程序。该过程涉及使用 THF 作为碘介导的光脱氢环化过程中产生的氢碘酸的清除剂。由于与环氧丙烷相比，THF的沸点更高、成本更低且易于获得，因此使用THF是有利的。该方法用于合成多种菲和螺旋。