2,6-Bis(4-methylphenyl)-1,6-heptadiene | 157367-55-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,6-Bis(4-methylphenyl)-1,6-heptadiene
• 英文别名: 4,4'-(hepta-1,6-diene-2,6-diyl)bis(methylbenzene)；1,6-Heptadiene, 2,6-bis(4-methylphenyl)-；1-methyl-4-[6-(4-methylphenyl)hepta-1,6-dien-2-yl]benzene
• CAS: 157367-55-0
• 化学式: C₂₁H₂₄
• 分子量: 276.422
• InChiKey: CFOREVYVYGHGPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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-Bis(4-methylphenyl)-1,6-heptadiene 在 2,4,6-triphenylpyrylium tetrafluoroborate 、 氧气 、 iron(II) bromide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.33h， 生成 1,5-di-p-tolylpentane-1,5-dione
  参考文献：
  名称：

  Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: direct evidence for nucleophilic O-1,2-aryl shifts

  摘要：

  1,5-Diaryt-6.7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph. 1e: Ar=p-MeC6H4. 1d: Ar=pMeOC(6)H(4)) were prepared by a modified method of photo-electron transfer oxygenation. and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(Il)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products. 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00166-1
• 作为产物：
  描述：

  戊二酰基二氯 在 正丁基锂 、 三氯化铝 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,6-Bis(4-methylphenyl)-1,6-heptadiene
  参考文献：
  名称：

  Griesbeck, Axel G.; Sadlek, Oliver; Polborn, Kurt, Liebigs Annalen, 1996, # 4, p. 545 - 549

  摘要：

  DOI：

文献信息

• Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes
  作者：Sheng Zhang、Deepika Bedi、Lu Cheng、Daniel K. Unruh、Guigen Li、Michael Findlater

  DOI：10.1021/jacs.0c02101

  日期：2020.5.13

  Stereoselective synthesis of trisubstituted alkenes is a long-standing challenge in organic chemistry, due to the small energy differences between E and Z isomers of trisubstituted alkenes (compared with 1,2-disubstituted alkenes). Transition metal-catalyzed isomerization of 1,1-disubstituted alkene can serve as an alternative approach to trisubsti-tuted alkenes, but it remains underdeveloped owing

  三取代烯烃的立体选择性合成是有机化学中长期存在的挑战，因为三取代烯烃的 E 和 Z 异构体之间的能量差异很小（与 1,2-二取代烯烃相比）。1,1-二取代烯烃的过渡金属催化异构化可以作为三取代烯烃的替代方法，但由于与反应效率和立体选择性有关的问题，它仍然不发达。在这里，我们展示了一种新型钴催化剂可以克服这些挑战，为获得广泛的三取代烯烃提供有效和立体选择性的途径。该协议与单烯和二烯兼容，并表现出良好的官能团耐受性和可扩展性。而且，它已被证明是构建有机发光体和氘代三取代烯烃的有用工具。对该机制的初步研究表明，该反应涉及钴氢化物途径。该反应的高立体选择性归因于 π-π 堆积效应和底物和催化剂之间的空间位阻。
• Electron-transfer induced intramolecular [2 + 2] cyloaddition of 2,6-diarylhepta-1,6-dienes
  作者：Yasutake Takahashi、Osamu Okitsu、Masatoshi Ando、Tsutomu Miyashi

  DOI：10.1016/s0040-4039(00)76711-6

  日期：1994.6

  Intramolecular [2 + 2] cycloaddition of 2,6-diaryl-1.6-heptadienes 1a-c to bicycloheptanes 2 can be induced by electron-transfer photosensitization with 9,10-dicyanoanthracene. A stepwise mechanism involving cyclic 1,4-cation radical 3 has been proposed based on the trapping experiments.
• Takahashi Yasutake, Okitsu Osamu, Ando Masatoshi, Miyashi Tsutomu, Tetrahedron Lett, 35 (1994) N 23, S 3953- 3956
  作者：Takahashi Yasutake, Okitsu Osamu, Ando Masatoshi, Miyashi Tsutomu

  DOI：——

  日期：——
• Griesbeck, Axel G.; Sadlek, Oliver; Polborn, Kurt, Liebigs Annalen, 1996, # 4, p. 545 - 549
  作者：Griesbeck, Axel G.、Sadlek, Oliver、Polborn, Kurt

  DOI：——

  日期：——
• Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: direct evidence for nucleophilic O-1,2-aryl shifts
  作者：Masaki Kamata、Motoko Ohta、Ken-ichi Komatsu、Hye-Sook Kim、Yusuke Wataya

  DOI：10.1016/s0040-4039(02)00166-1

  日期：2002.3

  1,5-Diaryt-6.7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph. 1e: Ar=p-MeC6H4. 1d: Ar=pMeOC(6)H(4)) were prepared by a modified method of photo-electron transfer oxygenation. and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(Il)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products. 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.