1,3-bis(4-vinylnaphthyl)propane, (VN-C3-VN) | 79541-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-bis(4-vinylnaphthyl)propane, (VN-C3-VN)
• 英文别名: 1,3-bis(4-vinylnaphthyl)propane；1-ethenyl-4-[3-(4-ethenylnaphthalen-1-yl)propyl]naphthalene
• CAS: 79541-70-1
• 化学式: C₂₇H₂₄
• 分子量: 348.488
• InChiKey: HYHMZFFFLUMJBE-UHFFFAOYSA-N

物化性质

• 沸点：
  533.4±30.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1,3-bis(4-vinylnaphthyl)propane, (VN-C3-VN) 以 苯 为溶剂， 反应 9.0h， 以35.1%的产率得到Hexacyclo[15.6.2.26,13.02,5.07,12.018,23]heptacosa-1(24),6(27),7,9,11,13(26),17(25),18,20,22-decaene
  参考文献：
  名称：

  苯乙烯衍生物对环烷的有效分子内 2 + 2 光环加成

  摘要：

  通过苯乙烯的光环二聚形成 1,2-二苯基环丁烷对苯乙烯浓度有相反的要求：具有短寿命活性物质的第一个二聚步骤需要高浓度的苯乙烯，而第二个环化步骤需要稀释条件以避免分子间副反应。为了通过将反应物限制为单个分子来克服这种单体浓度效应，在光照射下处理 ..cap α..,omega-双（乙烯基芳基）烷烃，这成功地提供了具有顺式双取代环丁烷环的环芳烃。总结了结果。

  DOI：

  10.1021/ja00251a053
• 作为产物：
  描述：

  cis,exo-1,2-ethano-syn-<2.3>naphthalenophane 在 三甲基苯基硅烷 作用下， 以 硝基苯-d5 为溶剂， 生成 1,3-bis(4-vinylnaphthyl)propane, (VN-C3-VN)
  参考文献：
  名称：

  Effects of the Linkage Length and Substituents on the Photocycloaddition of Bis(vinylnaphthyl)alkanes toward Naphthalenophanes

  摘要：

  Many naphtalenophanes, including a dicarbomethoxy-substituted one, a di-4-pyridyl-substituted one, and a bis(trimethylsilyl)-substituted one, were synthesized by applying intramolecular [2+2] photocycloaddition of α,ω-bis(1-vinylnaphthyl) alkanes. The effect of the linkage and substituents at the α and/or β positions of the vinyl groups was investigated concerning this photocycloaddition. From the results of the investigation, the limitation and scope of the photocycloaddition toward naphthalenophanes has been established.In addition to this preparative study, an anomalous transannular photoproduct, which was formed from cis, exo-1,2-ethano-syn-[2.3](1,4)naphthalenophane and analyzed by X-ray crystallography, was found to undergo thermal cycloreversion through diene and tetraene intermediates. The kinetics of this reversion were studied. Moreover, some obtained naphthalenophanes showed an interesting tendency to form 1 : 1 mixed crystals with small flat-shaped recrystallization solvents having donor substituents. This nature is also briefly reported.

  DOI：

  10.1246/bcsj.66.598

文献信息

• Intramolecular [2+2] Photocycloaddition. 5. Synthetic Methods toward [2.<i>n</i>]-, [3.<i>n</i>]-, and [4.<i>n</i>]Naphthalenophane Skeletons by Using α,ω-Bis(vinylnaphthyl)alkanes
  作者：Jun Nishimura、Motoharu Takeuchi、Hideo Takahashi、Eiji Ueda、Yasuhiro Matsuda、Akira Oku

  DOI：10.1246/bcsj.62.3161

  日期：1989.10

  [2+2] Photocycloaddition, cationic cyclocodimerization, and reductive ring enlargement were developed for the syntheses of [2.n]-, [3.n]-, and [4.n]naphthalenophanes, respectively, from α,ω-bis(vinylnaphthyl)alkanes as a single starting material. Using the exclusive syn selectivity of the former two methods, the room required for the intraannular naphthalene-ring rotation in the ring system is determined.

  以α,ω-双（乙烯基萘基）烷烃为单一起始原料，开发了[2+2]光环加成法、阳离子环化法和还原扩环法，分别用于合成[2.n]-、[3.n]-和[4.n]-萘烷。利用前两种方法独有的合成选择性，确定了环系统中环内萘环旋转所需的空间。
• Cationic cyclocodimerization. 2. Syntheses of [3.3](1,4)naphthalenophane and [3.3]paracyclo(1,4)naphthalenophane derivatives
  作者：Jun Nishimura、Tomohisa Okuda、Yoshihiko Mukai、Hidetoshi Hashiba、Akira Oku

  DOI：10.1016/s0040-4039(01)80195-7

  日期：——

  1,3-bis(4-vinylnaphthyl)propane and 1-(4-vinylnaphthyl)-3-(-vinylphenyl)propane, were cyclocodimerized with indene to afford indenyl-substituted [3.3](1,4)naphthalenophanes and [3.3]paracyclo(1,4)naphthalenophanes.

  1,3-双（4-乙烯基萘基）丙烷和1-（4-乙烯基萘基）-3-（-乙烯基苯基）丙烷与茚进行环二聚，得到茚基取代的[3.3]（1,4）萘甲酚和[3.3]对环（1,4）萘酚
• Cationic cyclocodimerization. 3. Syntheses of [3.3]paracyclo(1,4)naphthalenophane and [3.3](1,4)naphthalenophane derivatives. Stereoselectivity governed by the structures of .alpha.-naphthylmethylcarbenium ion and 1-vinylnaphthyl moiety
  作者：Jun Nishimura、Noriyuki Yamada、Tomohisa Okuda、Yoshihiko Mukai、Hidetoshi Hashiba、Akira Oku

  DOI：10.1021/jo00206a023

  日期：1985.3
• Nishimura Jun, Takeuchi Motoharu, Koike Masayuki, Sakamura Hideki, Yamash+, Bull. Chem. Soc. Jap., 66 (1993) N 2, S 598-606
  作者：Nishimura Jun, Takeuchi Motoharu, Koike Masayuki, Sakamura Hideki, Yamash+

  DOI：——

  日期：——
• NISHIMURA, JUN;OKUDA, TOMOHISA;MUKAI, YOSHIHIKO;HASHIBA, HIDETOSHI;OKU, A+, TETRAHEDRON LETT., 1984, 25, N 14, 1495-1498
  作者：NISHIMURA, JUN、OKUDA, TOMOHISA、MUKAI, YOSHIHIKO、HASHIBA, HIDETOSHI、OKU, A+

  DOI：——

  日期：——