(E)-(2-ethylpent-2-en-1-yl)benzene | 75473-95-9

• 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)-(2-ethylpent-2-en-1-yl)benzene
• 英文别名: (E)-(2-ethylpent-2-enyl)benzene；2-ethyl-1-phenyl-2-pentene；(E)-3-Benzyl-3-hexene；(E)-3-Benzylhex-3-ene；[(E)-2-ethylpent-2-enyl]benzene
• CAS: 75473-95-9
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: ILXOOXJJCCMRDS-XYOKQWHBSA-N

物化性质

• 沸点：
  243.8±10.0 °C(Predicted)
• 密度：
  0.879±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (3E)-3-iodo-3-hexene 、 bromozinc(1+),methanidylbenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 二异丁基氢化铝 作用下， 以79%的产率得到(E)-(2-ethylpent-2-en-1-yl)benzene
  参考文献：
  名称：

  通过钯催化的涉及苄基衍生物的交叉偶联高选择性合成烯丙基化的芳烃和二芳基甲烷

  摘要：

  苄基锌与链烯基卤化物或链烯基丙二烯与苄基卤化物的Pd催化交叉偶合为烯丙基化芳烃提供了高度选择性和快速的途径。

  DOI：

  10.1016/s0040-4039(01)90533-7

文献信息

• Oxidant-Free Direct Coupling of Internal Alkynes and 2-Alkylpyridine via Double C−H Activations by Alkylhafnium Complexes
  作者：Hayato Tsurugi、Koji Yamamoto、Kazushi Mashima

  DOI：10.1021/ja1100118

  日期：2011.2.2

  oxidant-free direct cross-coupling reaction of 2,6-lutidine and internal alkynes leading to five-membered carbocyclic compounds mediated by nonmetallocene cationic hafnium alkyl complexes. Mechanistic studies of the coupling reaction showed that the reaction begins with C(sp(3))-H bond activation via σ-bond metathesis, after which the coordinatively unsaturated hafnium center mediates further insertion

  我们开发了一种新型的 2,6-二甲基吡啶和内部炔烃的无氧化剂直接交叉偶联反应，导致由非茂金属阳离子铪烷基配合物介导的五元碳环化合物。偶联反应的机理研究表明，反应开始于 C(sp(3))-H 键通过 σ-键复分解活化，之后配位不饱和铪中心介导进一步的插入、迁移和 β-H 消除反应，得到从容易获得的底物制备五元碳环。
• The palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with allylic or benzylic bromides. Convenient syntheses of 1,4-alkadienes and allybenzenes from alkynes via hydroboration
  作者：Norio Miyaura、Takashi Yano、Akira Suzuki

  DOI：10.1016/s0040-4039(00)78629-1

  日期：1980.1

  The reactions of allylic or benzylic bromides with 1-alkenyldisiamylboranes readily available from 1-alkynes in the presence of sodium hydroxide and catalytic amounts of tetrakis-(triphenylphosphine)palladium to give corresponding 1,4-alkadienes or allylbenzenes in good yields.

  在氢氧化钠和催化量的四-（三苯基膦）钯的存在下，烯丙基或苄基溴化物与1-烯基二氮杂戊二烯易于从1-炔烃中反应，以高收率得到相应的1,4-链二烯或烯丙基苯。
• C(sp³)–H Alkenylation Catalyzed by Cationic Alkylhafnium Complexes: Stereoselective Synthesis of Trisubstituted Alkenes from 2,6-Dimethylpyridines and Internal Alkynes
  作者：Michael J. Lopez、Ai Kondo、Haruki Nagae、Koji Yamamoto、Hayato Tsurugi、Kazushi Mashima

  DOI：10.1021/acs.organomet.6b00655

  日期：2016.11.28

  Dibenzylhafnium complexes 3a d, supported by dianionic bidentate or tridentate ligands, upon activation via abstraction by either [Ph3C][B(C6F5)(4)] or B(C6F5)(3) served as catalysts for the C(sp(3))-H alkenylation of 2,6-dimethylpyridines with dialkylalkynes to give corresponding C(sp(3))-H alkenylated products 6. Complex 3c, containing a pyridine arm in the ligand skeleton, exhibited the highest catalytic activity among 3a d; initial addition of 2,6-dimethylpyridine (4a) to the C6D5Br solution of 3c followed by [Ph3C][B(C6F5)(4)] and 3-hexyne (5a) produced trisubstituted alkene 6aa in stereoselective manner in up to 50% yield without any byproducts, while the addition of 5a prior to 4a and [Ph3C][B(C6F5)(4)] to the C6D5Br solution of 3c generated 6aa, together with the formation of byproduct (E)-(2-ethylpent-2-en-1-yl)benzene (7). When an asymmetrical pyridine, 3-bromo-2,6-dimethylpyridine, was used as the coupling partner, the corresponding trisubstituted alkene was obtained selectively. Catalytically active cationic benzylhafnium complexes 8a-d, which were prepared by the reactions of 3a-d and B(C6F5)(3), respectively, were characterized by H-1, C-13, and F-19 NMR spectroscopy. Kinetic studies of the catalytic reaction between 4a and 4-octyne (5b) using 3c and [Ph3C][B(C6F5)(4)] in C6D5Br revealed that the catalytic reaction was zero-order for both 4a and 5b, indicating that the rate-determining step involved the C(sp3)-H bond activation of 4a by vinylhafnium intermediate 11c.
• Dishington, Allan P.; Douthwaite, Richard E.; Mortlock, Andrew, Journal of the Chemical Society. Perkin transactions I, 1997, # 3, p. 323 - 337
  作者：Dishington, Allan P.、Douthwaite, Richard E.、Mortlock, Andrew、Muccioli, Adriano B.、Simpkins, Nigel S.

  DOI：——

  日期：——
• MIYAURA N.; YANO T.; SUZUKI A., TETRAHEDRON LETT, 1980, 21, NO 30, 2865-2868
  作者：MIYAURA N.、 YANO T.、 SUZUKI A.

  DOI：——

  日期：——