(2E)-2-phenyl-2-nonene | 62135-01-7

• 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: (2E)-2-phenyl-2-nonene
• 英文别名: 2-phenyl-(E)-2-nonene；(E)-2-Phenylnon-2-en；[(E)-non-2-en-2-yl]benzene
• CAS: 62135-01-7
• 化学式: C₁₅H₂₂
• 分子量: 202.34
• InChiKey: DDCOXYZKGXIIFP-SDNWHVSQSA-N

物化性质

• 沸点：
  281.0±7.0 °C(Predicted)
• 密度：
  0.869±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  1,1-dibromo-1-octene 在 二(三叔丁基膦)钯 、 Cl₂Pd(DPEphos) 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2E)-2-phenyl-2-nonene
  参考文献：
  名称：

  Pd-catalyzed selective tandem arylation–alkylation of 1,1-dihalo-1-alkenes with aryl- and alkylzinc derivatives to produce α-alkyl-substituted styrene derivatives

  摘要：

  Trans-selective monoarylation of 1, 1-dibromo- and 1,1-dichloro-1-alkenes (1) can be achieved in > 80% yields and in > 98-99% stereo selectivity with arylzinc bromides in the presence of a catalytic amount of Cl2Pd(DPEphos) or Cl2Pd(dppb), the former permitting cleaner and higher yielding reactions. Although THF is a generally satisfactory solvent, ether and toluene are superior to THF in some cases. The second substitution of (Z)-alpha-bromostyrenes (3) with alkylzincs in the presence of 2 mol% of Pd('Bu3P)(2) proceeds to give the corresponding 2 in >90% yields and in greater than or equal to98-99% stereoselectivity. Although somewhat less satisfactory, the use of Cl2Pd(DPEphos) permits a one-pot tandem arylation-alkylation. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2003.09.008

文献信息

• Iron Catalyzed Isomerization of <scp>α‐Alkyl</scp> Styrenes to Access Trisubstituted Alkenes
  作者：Songgen Xu、Guixia Liu、Zheng Huang

  DOI：10.1002/cjoc.202000492

  日期：2021.3

  supported by phosphine‐pyridine‐oxazoline (PPO) ligand. The protocol provides an atom‐efficient and operationally simple approach to trisubstituted alkenes in high yields with excellent regio‐ and stereoselectivities under mild conditions. The results of deuterium‐labelling and radical trap experiments are consistent with an iron‐hydride pathway involving reversible alkene insertion and β‐H elimination.

  α-烷基苯乙烯的立体选择性异构化是通过使用膦-吡啶-恶唑啉（PPO）配体支持的新型铁催化剂完成的。该协议提供了一种原子效率高且操作简单的方法，可在温和条件下以高收率和出色的区域选择性和立体选择性对三取代烯烃进行生产。氘标记和自由基陷阱实验的结果与涉及可逆烯烃插入和β-H消除的铁氢化物途径一致。
• Silicon−(Thio)urea Lewis Acid Catalysis
  作者：Radim Hrdina、Christian E. Müller、Raffael C. Wende、Katharina M. Lippert、Mario Benassi、Bernhard Spengler、Peter R. Schreiner

  DOI：10.1021/ja110685k

  日期：2011.5.25

  We present a new class of catalysts based on the combination of N,N'-diaryl(thio)ureas and weak silicon Lewis acids (e.g., SiCl(4)). Such silicon-(thio)urea catalysts effectively catalyze the stereospecific rearrangement of epoxides to quaternary carbaldehydes.
• Vinylic organoboranes. 11. A highly stereospecific and regiospecific synthesis of trisubstituted alkenes via organoboranes
  作者：Herbert C. Brown、Narayan G. Bhat

  DOI：10.1021/jo00261a005

  日期：1988.12
• BROWN, HERBERT C.;BHAT, NARAYAN G., J. ORG. CHEM., 53,(1988) N6, C. 6009-6013
  作者：BROWN, HERBERT C.、BHAT, NARAYAN G.

  DOI：——

  日期：——
• XRIMYAN A. P.; MAKARYAN G. M.; BADANYAN SH. O., ARM. XIM. ZH., 39,(1986) N 9, 574-580
  作者：XRIMYAN A. P.、 MAKARYAN G. M.、 BADANYAN SH. O.

  DOI：——

  日期：——