1-phenylhex-4-en-1-one | 38376-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenylhex-4-en-1-one
• 英文别名: 4-Hexenophenone；(Z)-1-phenylhex-4-en-1-one
• CAS: 38376-73-7
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: KWNKUESVQADQHH-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-4-戊烯-1-酮 在 potassium tert-butylate 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 1-phenylhex-4-en-1-one
  参考文献：
  名称：

  Synthesis of polysubstituted tetrahydrofurans via Pd-catalyzed carboetherification reactions

  摘要：

  Pd-catalyzed carboetherifications of 1-, 2-, or 3-substituted gamma-hydroxy internal alkenes afford tetrahydrofuran products bearing three stereocenters in good yield with moderate to good stereoselectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.066

文献信息

• Selective Synthesis of <i>Z</i>-Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones
  作者：Sinem Guven、Gourab Kundu、Andrea Weßels、Jas S. Ward、Kari Rissanen、Franziska Schoenebeck

  DOI：10.1021/jacs.1c01797

  日期：2021.6.9

  the Z-selective synthesis of silyl enol ethers of (hetero)aromatic and aliphatic ketones via Ni-catalyzed chain walking from a distant olefin site. The positional selectivity is controlled by the directionality of the chain walk and is independent of thermodynamic preferences of the resulting silyl enol ether. Our mechanistic data indicate that a Ni(I) dimer is formed under these conditions, which

  我们报告了一种远程官能化策略，该策略允许通过 Ni 催化的链从远处的烯烃位点步行来Z选择性合成（杂）芳族和脂肪族酮的甲硅烷基烯醇醚。位置选择性由链游走的方向性控制，并且与所得甲硅烷基烯醇醚的热力学偏好无关。我们的机理数据表明，在这些条件下形成Ni (I)二聚体，作为催化剂静止状态，并在与烷基溴反应后转化为 [Ni (II) -H] 作为活性链行走/功能化催化剂，最终生成稳定的 η 3 键合Ni (II) 烯醇作为关键的选择性控制中间体。
• Dirhodium(<scp>ii</scp>)/P(<i>t</i>-Bu)₃ catalyzed tandem reaction of α,β-unsaturated aldehydes with arylboronic acids
  作者：Ziling Ma、Yuanhua Wang

  DOI：10.1039/c8ob01997e

  日期：——

  catalyst for the synthesis of aryl alkyl ketones by the tandem reaction of α,β-unsaturated aromatic or aliphatic aldehydes with arylboronic acids. This tandem procedure included arylation followed by the isomerization reaction. This method exhibits good functional group tolerance and has a broad substrate scope. With the conjugated aldehydes, the one-step synthesis of γ,δ-unsaturated ketones was realized

  提倡将膦连接的乙酸二铑（II）用作通过α，β-不饱和芳族或脂族醛与芳基硼酸的串联反应合成芳基烷基酮的催化剂。该串联过程包括芳基化，然后进行异构化反应。该方法表现出良好的官能团耐受性并且具有广泛的底物范围。通过共轭醛，通过该反应实现了γ，δ-不饱和酮的一步合成。值得注意的是，Rh-P键的长度是影响催化反应的重要因素。轴向烷基膦与芳基膦连接的二吡啶（II）晶体结构的比较分析）乙酸盐表明，与较长的Rh-P键相比，较短的Rh-P键长度有利于异构化过程。另外，反应完成后可以回收二吡啶（II）化合物。
• An easy synthesis of the 2-phenylsulfonyl-substituted allylic bromides and acetates and their reactivity towards nucleophiles
  作者：P. Auvray、P. Knochel、J.F. Normant

  DOI：10.1016/s0040-4039(00)85142-4

  日期：1986.1

  The reaction of phenyl vinyl sulfone with various aldehydes in the presence of a catalytic amount of DABCO furnishes in good yields teh corresponding 2-phenylsulfonyl-substituted alcohols which can be easily converted into their acetates or into their allylically rearranged bromides . These reagents, in turn, react with nucleophides (ketone enolates and cuprates) with an allylic rearrangement (SN2′

  在催化量的DABCO存在下，苯基乙烯基砜与各种醛的反应以良好的产率提供了相应的2-苯基磺酰基取代的醇，其可以容易地转化为其乙酸盐或烯丙基重排的溴化物。这些试剂，又与nucleophides（酮烯醇化物和铜酸盐）与烯丙基重排（S反应Ñ 2'机构），得到不饱和的官能化砜和。钯催化的反应使砜能够立体控制地转变为（Z，Z）跳过的1,4-二烯。
• Novel Synthetic Reactions Using Bis(2,2,2-trifluoroethoxy)diorganosulfuranes
  作者：Tomoya Kitazume、Nobuo Ishikawa

  DOI：10.1246/bcsj.53.2064

  日期：1980.7

  Alkoxy- or acyloxysulfuranes prepared in situ by the ligand exchange of bis(2,2,2-trifluoroethoxy)diorganosulfuranes with alcohols or carboxylic acids were found to behave as a potential alkylating or acylating reagent for the preparation of unsymmetrical sulfides, ketones, and esters.

  发现通过双（2,2,2-三氟乙氧基）二有机硫烷与醇或羧酸的配位交换原位制备的烷氧基或酰氧基硫烷可用作制备不对称硫化物、酮和酯的潜在烷基化或酰化试剂.
• Electrochemical alkene azidocyanation <i>via</i> 1,4-nitrile migration
  作者：Alex C. Seastram、Mishra Deepak Hareram、Thomas M. B. Knight、Louis C. Morrill

  DOI：10.1039/d2cc02958h

  日期：——

  An organic oxidant free electrochemical method for the azidocyanation of alkenes via 1,4-nitrile migration has been developed.

  已经开发出一种无机氧化剂的有机电化学方法，通过1,4-腈迁移，对烯烃进行氮化氰化反应。