E-1-(4'-methylphenyl)non-1-ene

• 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: E-1-(4'-methylphenyl)non-1-ene
• 英文别名: (E)-1-(4-methylphenyl)-1-nonene；1-methyl-4-[(E)-non-1-enyl]benzene
• 化学式: C₁₆H₂₄
• 分子量: 216.367
• InChiKey: RBLQGSBVNBYFLK-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  在 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.02h， 以0.357 g的产率得到E-1-(4'-methylphenyl)non-1-ene
  参考文献：
  名称：

  通过可控的β-羟基磺酰基中间体的顺/反片段化立体合成烯烃。

  摘要：

  酰化的三氟乙基链烷磺酸盐中羰基的还原遵循Felkin-Ahn选择性，并且根据反应条件，如此形成的非对映异构体β-羟基磺酰基中间体会发生合成和反片段化。实际上，以立体发散的方式形成异构的E-和Z-烯烃，其模仿了Peterson烯烃化反应的机理。

  DOI：

  10.1039/c9ob01563a

文献信息

• Hindered organoboron groups in organic chemistry. 23. The interactions of dimesitylboron stabilised carbanions with aromatic ketones and aldehydes to give alkenes.
  作者：Andrew Pelter、Dieter Buss、Eamon Colclough、Bakthan Singaram

  DOI：10.1016/s0040-4020(01)87981-3

  日期：1993.8

  Dimesitylboron stabilised carbanions react with diarylketones to give the corresponding alkenes in mild conditions with good yields. Reactions with aromatic aldehydes are more complex, but in all cases E-alkenes are available in good yields by trapping the intermediates with chlorotrimethylsilane followed by treatment with aq. HF/CH3CN. Treatment of the same intermediates with trifluoroacetic anhydride

  Dimesitylboron稳定的碳负离子与二芳基酮反应，在温和的条件下以良好的收率得到相应的烯烃。与芳族醛的反应更复杂，但是在所有情况下，通过用氯三甲基硅烷捕获中间体，然后用碳酸氢钠水溶液处理，可以以高收率获得E-烯烃。HF / CH 3 CN。用三氟乙酸酐处理相同的中间体主要得到Z-烯烃。考虑了这些重要过程的设计和机制。
• Stereoselective synthesis of E- and Z-alkenes by the boron–Wittig reaction
  作者：Andrew Pelter、Eieter Buss、Eamon Colclough

  DOI：10.1039/c39870000297

  日期：——

  Reactions of dimesitylboryl stablised carbanions with aromatic aldehydes produce erythro-intermediates, which can be trapped by trimethylsilylation or trifluoroacetylation to give products which can yield E- or Z-alkenes in good overall yields in new and controllable boron–Wittig reactions.

  二甲磺酰基稳定化碳负离子与芳族醛的反应生成赤型中间体，可通过三甲基甲硅烷基化或三氟乙酰化将其捕集，以新的和可控制的硼-维蒂希反应，以较高的总收率得到可以生产E-或Z-烯烃的产物。
• Olefination with Sulfonyl Halides and Esters: Scope, Limitations, and Mechanistic Studies of the Hawkins Reaction
  作者：Bartosz Górski、Alicja Talko、Tymoteusz Basak、Michał Barbasiewicz

  DOI：10.1021/acs.orglett.7b00517

  日期：2017.4.7

  Carbanions of alkanesulfonyl halides and esters react with nonenolizable carbonyl compounds to give olefins. Mechanistic studies reveal that initial aldol-type addition of the carbanions is followed by cyclization–fragmentation to alkenes, and the leaving group on the sulfonyl moiety (RSO2X) controls carbanion stability and rate of the olefin formation.

  链烷磺酰基卤化物和酯的碳负离子与不可烯化的羰基化合物反应生成烯烃。机理研究表明，最初的碳氢化合物以醛醇缩合形式加成环基后再裂解成烯烃，而磺酰基部分上的离去基团（RSO 2 X）控制着碳负离子的稳定性和烯烃形成的速率。
• Lewis Acid Promoted Carbon−Carbon Double-Bond Formation via Organozinc Reagents and Carbonyl Compounds
  作者：Zhi-Yong Peng、Fang-Fang Ma、Lv-Feng Zhu、Xiao-Min Xie、Zhaoguo Zhang

  DOI：10.1021/jo901252z

  日期：2009.9.4

  Using cheap and readily available AlCl3 as Lewis acid, functionalized aldehydes react with organozinc reagents to give (E)-alkenes stereoselectively in high yields.
• Wittig reaction with ion-supported Ph3P
  作者：Naoya Shimojuh、Yumi Imura、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2010.11.111

  日期：2011.2

  Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide A and N-methyl-N-[4(diphenylphosphino)benzyl]pyrrolidinium bromide B, were used for the Wittig reaction. Ion-supported phosphonium salts A1 and B1, which were prepared from the reactions of ion-supported Ph3P A and B with ethyl bromoacetate, respectively, reacted with aromatic and aliphatic aldehydes in the presence of K2CO3 to give the corresponding alpha,beta-unsaturated ethyl esters in good yields with high purity by simple filtration of the reaction mixture and subsequent removal of the solvent from the filtrate. Similarly, ion-supported phosphonium salts A2 and B2, which were prepared from the reactions of ion-supported Ph3P A and B with p-methylbenzyl bromide, respectively, reacted with aromatic and aliphatic aldehydes in the presence of NaH to provide the corresponding p-methylstyrene derivatives in good yields with high purity by simple filtration of the reaction mixture and the subsequent removal of the solvent from the filtrate. In both reactions, the co-product, ion-supported Ph3PO, could be obtained quantitatively by simple filtration, and was converted into the corresponding ion-supported Ph3P A and B again in high yields using dimethyl sulfate, followed by the reduction with LiAlH4. Recovered and regenerated ion-supported Ph3P A and B could be reused for the same Wittig reaction while maintaining good yields of ethyl (E)-3-(4'-chlorophenyl)-2-propenoate and 1 -(4'-chlorophenyl)-2-(4 ''-methylphenyl)ethene with high purity by simple filtration and removal of the solvent from the filtrate. (C) 2010 Elsevier Ltd. All rights reserved.