2,6-divinylnaphthalene | 35738-16-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-divinylnaphthalene
• 英文别名: 2,6-Divinylnaphthalin；2,6-Bis(ethenyl)naphthalene
• CAS: 35738-16-0
• 化学式: C₁₄H₁₂
• 分子量: 180.249
• InChiKey: JAZQIRAEJMLXFV-UHFFFAOYSA-N

物化性质

• 沸点：
  315.9±12.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  2,6-divinylnaphthalene 以 苯 为溶剂， 反应 6.0h， 以20%的产率得到<2.2>(2,6)-Naphthalenophane
  参考文献：
  名称：

  [2.2]Naphthalenophanes from intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes

  摘要：

  syn-[2.2]Naphthalenophanes were obtained exclusively in reasonable yields from the intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes. The position of the vinyl group and the type of vinyl substituent affected the isomer ratio of the products. The structures of naphthalenophanes were elucidated by H-1-NMR spectroscopy including COSY and NOESY experiments. Among the divinylnaphthalenes examined, 1,4-, 1,5-, and 1,6-ones did not give the desired naphthalenophanes. By taking advantage of the effect of the substituents on the photoreaction, we could obtain [2.2]-(1,5)naphthalenophane derivatives from 1,5-bis(beta-carbethoxyethenyl)naphthalene and 1,5-bis(beta-phenylethenyl)naphthalene, but we could not obtain the 1,4-isomers, probably because they are highly strained. Although a mixture of two different divinylnaphthalenes was irradiated, only homo-adducts were obtained; no cross adducts were detected.

  DOI：

  10.1021/jo00078a016
• 作为产物：
  描述：

  2,6-萘二羧酸 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 甲基三苯基溴化膦 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 为溶剂， 生成 2,6-divinylnaphthalene
  参考文献：
  名称：

  一种新型供体-π-受体卤色2,6-二苯乙烯基萘发色团：合成、光物理性质和DFT研究

  摘要：

  在这项研究中，一种新的2,6-二苯乙烯基萘[2-((4-(( E )-2-(6-(( E )-2,4-双(甲磺酰基)苯乙烯基)萘-2-基)乙烯基) )苯基)(乙基)氨基)1-乙醇;以Heck化学为主要反应成功合成了ASDSN ]。 ASDSN化合物是一种供体-π-受体(D-π-A)共轭体系，其中氨基作为给电子基团，磺酰基作为吸电子基团。在一些不同溶剂中， ASDSN的紫外-可见吸收在 403–417 nm 范围内观察到，具有高摩尔消光系数 ( ε = 15 300–56 200 M −1 cm −1 )。这种新型荧光2,6-二苯乙烯基萘化合物在可见光谱（557 nm）的黄色区域发射光，斯托克斯位移为5930 cm -1 。 ASDSN是一种 pH 响应性荧光化合物，在中性形式下显示黄色荧光，在质子化形式下显示蓝色荧光。在 pH = 3.0 时观察到发色团的白光发射 (WLE)。 ASDSN

  DOI：

  10.1039/d0ra08508a

文献信息

• Structure-performance correlations of cross-linked boronic acid polymers as adsorbents for recovery of fructose from glucose–fructose mixtures
  作者：Guido Schroer、Jeff Deischter、Tobias Zensen、Jan Kraus、Ann-Christin Pöppler、Long Qi、Susannah Scott、Irina Delidovich

  DOI：10.1039/c9gc03151k

  日期：——

  This article addresses the utilization of cross-linked phenylboronic-acid polymers for fructose separation from glucose–fructose mixtures focusing particularly on structure-sorption relationships.

  本文讨论了交联苯硼酸聚合物在葡萄糖-果糖混合物中分离果糖的利用，特别关注结构-吸附关系。
• A Highly Efficient Synthesis of a Naphthalenoid Histamine-3 Antagonist
  作者：Yi-Yin Ku、Tim Grieme、Yu-Ming Pu、Ashok V. Bhatia

  DOI：10.1002/adsc.200900162

  日期：2009.8

  chemical steps and a salt formation step in 36% overall yield from 6-bromo-2-naphthalenol 9. The key features are a regioselective Suzuki coupling protocol for selective vinylation of 12 with potassium vinyltrifluoroborate in high yield (92%) with excellent regioselectivity (90:2) and a base-catalyzed hydroamination reaction of 11 in an anti-Markovnikov fashion under mild reaction conditions. An optimized

  有效的和选择性的组胺3受体拮抗剂1A的高效合成是通过四个化学步骤和成盐步骤完成的，其中6-溴-2-萘酚9的总收率为36％。主要特征是区域选择性Suzuki偶联方案，可高产率（92：9）以优异的区域选择性（90：2）选择性地用乙烯基三氟硼酸钾选择性乙烯基化12，并在温和反应下以反马尔科夫尼可夫的方式进行11的碱催化加氢胺化反应情况。优化的铜催化交叉偶联反应用于掺入哒嗪酮4。
• Blank, Norman E.; Haenel, Matthias W., Chemische Berichte, 1981, vol. 114, # 4, p. 1520 - 1530
  作者：Blank, Norman E.、Haenel, Matthias W.

  DOI：——

  日期：——
• [2.2]Naphthalenophanes from intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes
  作者：Motoharu Takeuchi、Takeshi Tuihiji、J. Nishimura

  DOI：10.1021/jo00078a016

  日期：1993.12

  syn-[2.2]Naphthalenophanes were obtained exclusively in reasonable yields from the intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes. The position of the vinyl group and the type of vinyl substituent affected the isomer ratio of the products. The structures of naphthalenophanes were elucidated by H-1-NMR spectroscopy including COSY and NOESY experiments. Among the divinylnaphthalenes examined, 1,4-, 1,5-, and 1,6-ones did not give the desired naphthalenophanes. By taking advantage of the effect of the substituents on the photoreaction, we could obtain [2.2]-(1,5)naphthalenophane derivatives from 1,5-bis(beta-carbethoxyethenyl)naphthalene and 1,5-bis(beta-phenylethenyl)naphthalene, but we could not obtain the 1,4-isomers, probably because they are highly strained. Although a mixture of two different divinylnaphthalenes was irradiated, only homo-adducts were obtained; no cross adducts were detected.
• A novel donor–π–acceptor halochromic 2,6-distyrylnaphthalene chromophore: synthesis, photophysical properties and DFT studies
  作者：Farhad Panahi、Ali Mahmoodi、Sajjad Ghodrati、Fazlolah Eshghi

  DOI：10.1039/d0ra08508a

  日期：——

  In this study a new 2,6-distyryl naphthalene [2-((4-((E)-2-(6-((E)-2,4-bis(methylsulfonyl)styryl)naphthalen-2-yl)vinyl)phenyl)(ethyl)amino)ethan-1-ol; ASDSN] was synthesized successfully using Heck chemistry as the main reaction. The ASDSN compound is a donor–pi–acceptor (D–π–A) conjugated system with amino as electron donating and sulfonyl as electron withdrawing groups. The UV-vis absorption of ASDSN

  在这项研究中，一种新的2,6-二苯乙烯基萘[2-((4-(( E )-2-(6-(( E )-2,4-双(甲磺酰基)苯乙烯基)萘-2-基)乙烯基) )苯基)(乙基)氨基)1-乙醇;以Heck化学为主要反应成功合成了ASDSN ]。 ASDSN化合物是一种供体-π-受体(D-π-A)共轭体系，其中氨基作为给电子基团，磺酰基作为吸电子基团。在一些不同溶剂中， ASDSN的紫外-可见吸收在 403–417 nm 范围内观察到，具有高摩尔消光系数 ( ε = 15 300–56 200 M −1 cm −1 )。这种新型荧光2,6-二苯乙烯基萘化合物在可见光谱（557 nm）的黄色区域发射光，斯托克斯位移为5930 cm -1 。 ASDSN是一种 pH 响应性荧光化合物，在中性形式下显示黄色荧光，在质子化形式下显示蓝色荧光。在 pH = 3.0 时观察到发色团的白光发射 (WLE)。 ASDSN