1,2,3,4-tetraethyl-5-methylbenzene | 29344-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,3,4-tetraethyl-5-methylbenzene
• 英文别名: 1-Methyl-2,3,4,5-tetraaethylbenzol；Tetraethyltoluene
• CAS: 29344-64-7
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: MGCUGDIHZZBPNV-UHFFFAOYSA-N

物化性质

• 沸点：
  263.2±35.0 °C(Predicted)
• 密度：
  0.862±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,3,4,5-Tetraaethylbenzylchlorid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 1,2,3,4-tetraethyl-5-methylbenzene
  参考文献：
  名称：

  五甲基苯、五乙基苯和一些混合五烷基苯硝化得到的异常产物

  摘要：

  五甲基苯用发烟硝酸硝化，主要得到硝基五甲基苯和硝酸2,3,4,5-四甲基苄基酯的混合物。没有形成任何显着量的其他异构硝酸盐。6-Nitro-2,3,4,5-四甲基苄基硝酸酯，2,3,4,5-四甲基苯甲醇，2,3,4,5-四甲基苯甲醛，2,2',3,3',4,4' ,5,5',6-九甲基二苯基甲烷和2,2',3,3',4,4',5,5'-八甲基-6-硝基甲基二苯基甲烷是次要产物。五乙基苯得到硝基五乙基苯和α-甲基-2,3,4,5-四乙基苄基硝酸酯的混合物以及一些氧化产物。优先侧链攻击发生在未取代的环位置邻位的伯烷基。因此，发现 1-甲基-2,3,4,5-四乙基苯产生几乎等量的硝酸苄酯和 α-甲基硝酸苄酯，

  DOI：

  10.1246/bcsj.43.473

文献信息

• Benzannulation from Alkynes and Allyl Tosylates via a π-Allylpalladium Intermediate
  作者：Naofumi Tsukada、Shuichi Sugawara、Yoshio Inoue

  DOI：10.1021/ol991406n

  日期：2000.3.1

  [reaction: see text] Allyl tosylate is a good allyl source for a novel palladium-catalyzed benzannulation that affords polysubstituted benzenes from 1 mol of an allyl compound and 2 mol of internal alkynes. Using triphenyl phosphite as a ligand, the reaction with terminal alkynes gave trisubstituted benzenes regioselectively.

  [反应：参见正文]甲苯磺酸烯丙基酯是新型钯催化的苯环烷基化物的良好烯丙基来源，该苯环烷基化物由1摩尔的烯丙基化合物和2摩尔的内部炔烃提供多取代的苯。使用亚磷酸三苯酯作为配体，与末端炔烃的反应区域选择性地产生三取代的苯。
• Palladium-Catalyzed Benzannulation from Alkynes and Allylic Compounds
  作者：Naofumi Tsukada、Shuichi Sugawara、Keiichiro Nakaoka、Yoshio Inoue

  DOI：10.1021/jo026857r

  日期：2003.7.1

  Various alkynes reacted with allyl tosylates in the presence of palladium catalysts, giving polysubstituted benzenes with good to high regioselectivity. Pentasubstituted and trisubstituted benzenes were readily prepared by reaction of internal alkynes and terminal alkynes, respectively. The combination of allyl alcohols and p-toluenesulfonic anhydride could be utilized in place of isolated allyl tosylates. The cyclization of diynes with allyl tosylate afforded bicyclic compounds containing an aromatic ring.
• Reaction of zirconacyclopentadienes with electrophiles such as benzaldehyde, methyl methacrylate and 1-bromo-2-butyne after treatment with RLi
  作者：Takashi Seki、Yoshinori Noguchi、Duan Zheng、Wen-Hua Sun、Tamotsu Takahashi

  DOI：10.1016/j.tetlet.2004.10.030

  日期：2004.11

  Zirconacyclopentadienes reacted with electrophiles after treatment with alkyllithium. For example, the reaction with benzaldehyde after treatment with methyllithium to give a nucleophilic addition product of a dienyl moiety to aldehyde, dienylcarbinol, in a moderate yield. Similar reaction of a zirconacyclopentadiene using butyllithium with methyl methacrylate afforded a Michael addition product in a good yield. Treatment of zirconacyclopentadienes with n-BuLi followed by 1-bromo-2-butyne gave a mono-propargylated diene derivative in 95% yield after hydrolysis. When propargyl chloride was treated with n-BuLi first and then added to zirconacyclopentadienes, penta-substituted benzene derivatives were formed in high yields. (C) 2004 Published by Elsevier Ltd.
• Anomalous Products Obtained by Nitration of Pentamethylbenzene, Pentaethylbenzene, and Some Mixed Penta-alkylbenzenes
  作者：Hitomi Suzuki、Kiyomi Nakamura

  DOI：10.1246/bcsj.43.473

  日期：1970.2

  Pentamethylbenzene has been nitrated with fuming nitric acid to give mainly a mixture of nitropentamethylbenzene and 2,3,4,5-tetramethylbenzyl nitrate. Other isomeric nitrates were not formed in any significant amount. 6-Nitro-2,3,4,5-tetramethylbenzyl nitrate, 2,3,4,5-tetramethylbenzyl alcohol, 2,3,4,5-tetramethylbenzaldehyde, 2,2′,3,3′,4,4′,5,5′,6-nonamethyldiphenylmethane, and 2,2′,3,3′,4,4′,5,

  五甲基苯用发烟硝酸硝化，主要得到硝基五甲基苯和硝酸2,3,4,5-四甲基苄基酯的混合物。没有形成任何显着量的其他异构硝酸盐。6-Nitro-2,3,4,5-四甲基苄基硝酸酯，2,3,4,5-四甲基苯甲醇，2,3,4,5-四甲基苯甲醛，2,2',3,3',4,4' ,5,5',6-九甲基二苯基甲烷和2,2',3,3',4,4',5,5'-八甲基-6-硝基甲基二苯基甲烷是次要产物。五乙基苯得到硝基五乙基苯和α-甲基-2,3,4,5-四乙基苄基硝酸酯的混合物以及一些氧化产物。优先侧链攻击发生在未取代的环位置邻位的伯烷基。因此，发现 1-甲基-2,3,4,5-四乙基苯产生几乎等量的硝酸苄酯和 α-甲基硝酸苄酯，