2-benzyl-hex-5-enal | 22859-84-3

• 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: 2-benzyl-hex-5-enal
• 英文别名: 2-Benzylhex-5-enal
• CAS: 22859-84-3
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: ALQUGXFPEPVRLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyl-hex-5-enal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 triazolium salt-based catalyst 双(三甲基硅烷基)氨基钾 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (3-benzyl-2-oxo-cyclopentyl)-acetic acid methyl ester
  参考文献：
  名称：

  The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction

  摘要：

  A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2,3- and 2,4disubstituted cyclopentanones. The Stetter reaction of 2,5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis-diasteroiners with low ee. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.121
• 作为产物：
  描述：

  hydrocinnamaldehyde N,N-dimethylhydrazone 在 amberlyst-15 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 2-benzyl-hex-5-enal
  参考文献：
  名称：

  The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction

  摘要：

  A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2,3- and 2,4disubstituted cyclopentanones. The Stetter reaction of 2,5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis-diasteroiners with low ee. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.121

文献信息

• A Tandem Amino-Cope Rearrangement/Enamine Alkylation Reaction
  作者：Steven Allin、Martin Button、Stephen Shuttleworth

  DOI：10.1055/s-1997-3248

  日期：1997.6

  Thermally induced [3,3]-sigmatropic rearrangement of 3-amino-1,5-diene substrates occurs to give the corresponding enamine products in high yield and with excellent trans:cis enamine selectivity. The enamine produced during the amino-Cope rearrangement has been directly derivatized, representing the first report of a tandem amino-Cope rearrangement/enamine alkylation reaction. The potential of this novel synthetic strategy is outlined.

  热诱导的3-氨基-1,5-二烯底物的[3,3]-σ-转位重排反应生成相应的烯胺产物，产率高且具有优良的反式:顺式烯胺选择性。在氨基-科普重排反应中产生的烯胺已被直接衍生化，代表了串联氨基-科普重排/烯胺烷基化反应的首次报道。概述了这一新型合成策略的潜力。
• Aldehydes from dihydro-1,3-oxazines. V. A three carbon chain extention leading to α,β-disubstituted propionaldehydes
  作者：A.I. Meyers、A.C. Kovelesky

  DOI：10.1016/s0040-4039(01)88011-4

  日期：1969.1
• US4131623A
  申请人：——

  公开号：US4131623A

  公开（公告）日：1978-12-26
• The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction
  作者：Nathan T. Reynolds、Tomislav Rovis

  DOI：10.1016/j.tet.2005.03.121

  日期：2005.6

  A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2,3- and 2,4disubstituted cyclopentanones. The Stetter reaction of 2,5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis-diasteroiners with low ee. (c) 2005 Elsevier Ltd. All rights reserved.