(E)-1-(3-nitrophenyl)-1-pentene

• 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-(3-nitrophenyl)-1-pentene
• 英文别名: 1-nitro-3-[(E)-pent-1-enyl]benzene
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: ZKYFVUBTTUTOIK-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-[Hydroxy-(3-nitro-phenyl)-methyl]-nonan-5-one 在 三氟化硼 作用下， 以 四氯化碳 为溶剂， 以62%的产率得到(E)-1-(3-nitrophenyl)-1-pentene
  参考文献：
  名称：

  Boron trifluoride induced fragmentation of β-aryl-β-hydroxyketones

  摘要：

  beta-Aryr-beta-hydroxy ketones ate readily cleaved by boron trifluoride in non-protic solvents. The reaction appears to proceed via a non-synchronous Grobe fragmentation pathway. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01777-8

文献信息

• A tandem Aldol-Grob reaction of ketones with aromatic aldehydes
  作者：George W. Kabalka、David Tejedor、Nan-Sheng Li、Rama R. Malladi、Sarah Trotman

  DOI：10.1016/s0040-4020(98)00976-4

  日期：1998.12

  Aromatic aldehydes react with ketones to produce(E)-1-aryl-1-alkenes via a tandem Aldol-Grob cleavage reaction sequence. The reaction, initiated by boron trifluoride, also produces a carboxylic acid fragment.

  芳香醛与酮反应，通过串联的Aldol-Grob裂解反应序列生成（E）-1-芳基-1-烯烃。由三氟化硼引发的反应也产生羧酸片段。
• The Aldol-Grob Reaction: Regioselective Synthesis of (E)-Alkenes from Aldehydes and Ketones with Ytterbium Triflate Catalysis
  作者：Massimo Curini、Francesco Epifano、Federica Maltese、Maria Carla Marcotullio

  DOI：10.1002/ejoc.200300076

  日期：2003.5

  A simple, good yielding and solvent-free aldol-Grob reaction sequence, catalysed by Yb(OTf)3 hydrate, affording (E)-alkenes regioselectively from aldehydes and ketones is described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  描述了一种简单、产率高且无溶剂的 aldol-Grob 反应序列，由 Yb(OTf)3 水合物催化，从醛和酮中区域选择性地提供 (E)-烯烃。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Synthesis of (<i>E</i>)-1-Aryl-1-alkenes via a Novel BF₃·OEt₂-Catalyzed Aldol−Grob Reaction Sequence
  作者：George W. Kabalka、Nan-Sheng Li、David Tejedor、Rama R. Malladi、Sarah Trotman

  DOI：10.1021/jo9822784

  日期：1999.4.1

  The reactions of aromatic aldehydes with ketones in the presence of various acids were examined. The reactions generate (E)-1-aryl-1-alkenes in the presence of boron trifluoride diethyl etherate in nonnucleophilic solvents.
• Simple protocol for enhanced (E)-selectivity in Julia–Kocienski reaction
  作者：Jiří Pospíšil

  DOI：10.1016/j.tetlet.2011.02.086

  日期：2011.5

  A short and efficient Julia-Kocienski olefination protocol, based upon the use of chelating agents (18-crown-6 or TDA-1 for K(+); 12-crown-4 or HMPA for Li(+)), was developed. This protocol enhances the (E)selectivity of the reaction and the desired olefins are obtained generally with >10:1 (E/Z)-selectivity. (C) 2011 Elsevier Ltd. All rights reserved.