1,4-Divinylnaphthalene | 92159-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-Divinylnaphthalene
• 英文别名: 1,4-Bis(ethenyl)naphthalene
• CAS: 92159-71-2
• 化学式: C₁₄H₁₂
• 分子量: 180.249
• InChiKey: VZORBIIKPJNHTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 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：

  (+)-(S)-2-(p-tolylsulfinyl)cyclohexa-2,5-diene-1,4-dione 、 1,4-Divinylnaphthalene 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 hexacyclo[16.8.0.02,11.03,8.012,17.021,26]hexacosa-1(18),2(11),3(8),5,9,12,14,16,19,21(26),23-undecaene-4,7,22,25-tetrone 、 hexacyclo[16.8.0.02,11.03,8.012,17.021,26]hexacosa-1(18),2(11),3(8),5,9,12,14,16,19,21(26),23-undecaene-4,7,22,25-tetrone
  参考文献：
  名称：

  Enantioselective Approach to Both Enantiomers of Helical Bisquinones

  摘要：

  DOI：

  10.1021/jo981919s
• 作为产物：
  描述：

  1-溴-4-(溴甲基)萘 在 四(三苯基膦)钯 sodium hydroxide 、 对叔丁基邻苯二酚 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 9.0h， 生成 1,4-Divinylnaphthalene
  参考文献：
  名称：

  Enantioselective Approach to Both Enantiomers of Helical Bisquinones

  摘要：

  DOI：

  10.1021/jo981919s

文献信息

• Tetrahydronaphthalene-1,4-dione and its Chromiumtricarbonyl Complex
  作者：Álvaro Enríquez García、E. Peter Kündig、Thierry Lomberget、Ryan Bragg、Cyril Poulard、Gerald Bernardinelli

  DOI：10.2533/chimia.2007.169

  日期：——

  The article gives a brief outline of the rediscovery of tetrahydronaphthalene-1,4-dione, a stable tautomer which has been known for over half a century but has not been applied in synthesis. Desymmetrization is readily achieved via enantioselective reduction. Synthetic potential apart, the dione and its chromiumtricarbonyl complex are of theoretical interest. Thus, whereas dihydroxynaphthalene requires quite harsh conditions and leads to a 1:1 mixture of the two tautomers, the chromiumtricarbonyl complex of dihydroxynaphthalene tautomerizes under very mild conditions to the tetrahydronaphthalene-1,4-dione complex. An earlier literature report showed that in trifluoroacetic acid, the dione tautomer is present exclusively. This has now been used to isolate multigram quantities of the compound.

  这篇文章简要介绍了四氢萘-1,4-二酮的重新发现，这是一种稳定的互变异构体，已知已有半个世纪，但尚未应用于合成。通过对映选择性还原，可以轻松实现非对称化。除了合成潜力外，这种二酮及其铬三羰基配合物也具有理论兴趣。因此，虽然二氢萘酚需要相当严酷的条件，并导致两种互变异构体的1:1混合物，但二氢萘酚的铬三羰基配合物在非常温和的条件下发生互变异构，形成四氢萘-1,4-二酮配合物。早期的文献报告表明，在三氟乙酸中，只存在二酮互变异构体。现在已经利用这一点来分离多克量的化合物。
• [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.
• Enantioselective Approach to Both Enantiomers of Helical Bisquinones
  作者：M. Carmen Carreño、Raquel Hernández-Sánchez、Jesús Mahugo、Antonio Urbano

  DOI：10.1021/jo981919s

  日期：1999.2.1