(E)-2,2',4,4'-tetramethylstilbene | 51042-16-1

• 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)-2,2',4,4'-tetramethylstilbene
• 英文别名: 1-[(E)-2-(2,4-dimethylphenyl)ethenyl]-2,4-dimethylbenzene
• CAS: 51042-16-1
• 化学式: C₁₈H₂₀
• 分子量: 236.357
• InChiKey: UMACGPDMSYRKKG-MDZDMXLPSA-N

物化性质

• 熔点：
  107-109 °C
• 沸点：
  350.4±37.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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)-2,2',4,4'-tetramethylstilbene 在 碘 、 氧气 、 三氟乙酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 20.0h， 以71%的产率得到2,4-二甲基苯甲醛
  参考文献：
  名称：

  Photooxidative Cleavage of Aromatic Alkenes into Aldehydes Using Catalytic Iodine and Molecular Oxygen under Visible Light Irradiation

  摘要：

  We report a method for the photooxidative cleavage of aromatic alkenes to give aldehydes using molecular oxygen as the terminal oxidant, visible light, a catalytic amount of iodine and trifluoroacetic acid.

  DOI：

  10.1055/s-0033-1340735
• 作为产物：
  描述：

  2,4-二甲基苯甲醛 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以66%的产率得到(E)-2,2',4,4'-tetramethylstilbene
  参考文献：
  名称：

  Molecular structure and intramolecular motion of (E)-stilbenes in crystals. An interpretation of the unusually short ethylene bond

  摘要：

  Crystal structures of (E)-2,2'-dimethylstilbene (2), (E)-2,2',4,4'-tetramethylstilbene (3), (E)-2,2',5,5'-tetramethylstilbene (4), (E)-2,2',4,4',5,5'-hexamethylstilbene (5), and (E)-2,2',3,3-tetramethylstilbene (6) were determined at several temperatures by X-ray diffraction. Analyses of these results and also of those reported for (E)-stilbene (1) and its related compounds revealed that the X-ray structures of compounds having the (E)-stilbene skeleton commonly show an unusually short bond length for the ethylene bond and a strong temperature dependence for the molecular structure. No sign confirming these anomalies could be detected in solution by NMR or UV spectroscopy. It is concluded that the short ethylene bond in the X-ray structures of these compounds is an artifact caused by dynamic averaging originating from the torsional vibration of the C-Ph bonds, during which the movement of the benzene rings is restrained to be a minimum. The observed temperature dependence of the ethylene bond length and angles and of the torsion angles of the C-Ph bonds is ascribed to the slight energy difference between the conformers, which interconvert by the torsional vibration. It has also been revealed that the rotational vibration of the benzene rings around the normal axes through C1 and C1' is a characteristic motion of (E)-stilbenes in the crystalline state.

  DOI：

  10.1021/ja00029a037

文献信息

• A Novel Synthetic Approach to Biphenyls
  作者：Tong-Ing Ho、Cheng-Shein Shu、Ming-Kuo Yeh、Fa-Ching Chen

  DOI：10.1055/s-1987-28076

  日期：——

  Two novel biphenyls, 2,2′-bis(1-hydroxyethyl)-3,3′,5,5′-tetramethylbiphenyl (7) and 2,2′-bis(1-hydroxyethyl)-4,4′,6,6′-tetramethylbiphenyl (13) were synthesized through Wittig reaction, photochemical oxidative cyclization, and ozonolysis, using xylene and mesitylene as starting materials. The novel approach is applicable to both symmetrical and unsymmetrical biphenyls.

  两种新型的双联苯化合物，2,2'-双(1-羟乙基)-3,3',5,5'-四甲基双联苯（7）和2,2'-双(1-羟乙基)-4,4',6,6'-四甲基双联苯（13），通过Wittig反应、光化学氧化环合及臭氧分解，以二甲苯和间二甲苯为起始原料合成。该新颖方法是适用于对称和非对称双联苯合成的通用方法。
• Simple Ruthenium Precatalyst for the Synthesis of Stilbene Derivatives and Ring-Closing Metathesis in the Presence of Styrene Initiators
  作者：Cheikh Lo、Renan Cariou、Cédric Fischmeister、Pierre H. Dixneuf

  DOI：10.1002/adsc.200600493

  日期：2007.3.5

  The ruthenium complex RuCl2(p-cymene)(IMes) was found to be an efficient precatalyst, with styrene as an initiating species, for the alkene metathesis of various styrenes into symmetrical and unsymmetrical stilbene derivatives and for the ring-closing metathesis reaction of a sterically hindered olefin leading to a tetrasubstituted cycloolefin.

  钌络合物RuCl 2（p- cymene）（IMes）被发现是一种有效的预催化剂，以苯乙烯为起始物种，可用于将各种苯乙烯进行烯烃复分解为对称和不对称的1,2-二苯乙烯衍生物，以及用于开环的闭环复分解反应。导致四取代的环烯烃的位阻烯烃。
• Synthesis of Styrenes and <i>E‐</i>Stilbenes by Palladium‐Catalyzed Vinylation of Aryl Iodides with 1,2‐Dibromoethane
  作者：Guangfa Shi、Xiaotian Ma、Qiongqiong Zhu、Yanghui Zhang

  DOI：10.1002/adsc.202301146

  日期：2024.3.8

  The Pd-catalyzed vinylation reactions of aryl iodides using 1,2-dibromoethane is developed for the synthesis of styrenes and stilbenes. In these reactions, vinyl bromide is generated from 1,2-dibromoethane and then undergoes reductive cross-coupling with aryl iodides, affording styrene products. Under slightly modified reaction conditions, styrenes can continue reacting with vinyl bromide to form E-stilbenes

  使用 1,2-二溴乙烷的钯催化芳基碘化物乙烯基化反应被开发用于合成苯乙烯和茋。在这些反应中，溴乙烯由 1,2-二溴乙烷产生，然后与芳基碘进行还原交叉偶联，得到苯乙烯产物。在稍加修改的反应条件下，苯乙烯可以继续与溴乙烯反应生成E-二苯乙烯，这提供了二苯乙烯的一锅合成方法。醇，包括异丙醇和甲醇，在这些还原交叉偶联反应中用作还原剂。
• Elbs; Foerster, Journal fur praktische Chemie (Leipzig 1954), 1889, vol. <2> 39, p. 299
  作者：Elbs、Foerster

  DOI：——

  日期：——
• Hepp, Chemische Berichte, 1874, vol. 7, p. 1409
  作者：Hepp

  DOI：——

  日期：——