(E)-1-(4-methoxyphenyl)hex-1-en-3-one | 82297-65-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(4-methoxyphenyl)hex-1-en-3-one
• 英文别名: t1-(4-methoxy-phenyl)-hex-1-en-3-one；t1-(4-Methoxy-phenyl)-hex-1-en-3-on；1t-(4-Methoxy-phenyl)-hex-1-en-3-on
• CAS: 82297-65-2
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: CQYZXONYJFSVDK-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氢氧化钡 以79%的产率得到
  参考文献：
  名称：

  GARCIA-RASO, A.;SINISTERRA, J. V.;MARINAS, J. M., POL. J. CHEM., 1982, 56, N 10-12, 1435-1445

  摘要：

  DOI：

文献信息

• Regioselective Heck Vinylation of Electron-Rich Olefins with Vinyl Halides: Is the Neutral Pathway in Operation?
  作者：Matthew McConville、Ourida Saidi、John Blacker、Jianliang Xiao

  DOI：10.1021/jo802781m

  日期：2009.4.3

  Highly regioselective vinylation of electron-rich olefins by bromo- as well as chlorostyrenes is effected by palladium catalysis with either mono- or bidentate phosphines in a molecular solvent, with no need for halide scavengers, ionic liquids, or ionic additives. The use of the hemilabile 1,3-bis(diphenylphosphino)propane monoxide (dpppO) as a ligand led to faster reactions of more challenging 2-substituted

  溴和氯苯乙烯对富电子烯烃的高度区域选择性乙烯基化是通过在分子溶剂中用单或二齿膦进行钯催化来实现的，不需要卤化物清除剂，离子液体或离子添加剂。半不稳定的1,3-双（二苯基膦基）丙烷一氧化碳（dpppO）作为配体的使用导致更具挑战性的2-取代乙烯基醚的反应更快，并降低了Pd的负载量。与相关的芳基化反应相反，证据表明乙烯基化可能通过中性的Heck机制进行。
• Palladium-Catalysed Heck Reactions of Alk-1-en-3-ones with Aryl Bromides: A Very Simple Access to (<i>E</i>)-1-Arylalk-1-en-3-ones
  作者：Mhamed Lemhadri、Yacoub Fall、Henri Doucet、Maurice Santelli

  DOI：10.1055/s-0028-1087976

  日期：——

  When appropriate reaction conditions are used, very high yields of (E)-1-arylalk-1-en-3-one derivatives can be obtained by palladium-catalysed reactions of alk-1-en-3-ones with aryl bromides. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane in combination with [Pd(C3H5)Cl]2 was found to be a very efficient catalyst for this reaction. In general, higher reaction rates were observed with electron-poor aryl bromides, but the electron-rich aryl bromides 1-bromo-4-(dimethylamino)benzene and 4-bromoanisole also led to the arylated enones in high yields. Even with sterically very congested aryl bromides such as 9-bromoanthracene, 1-bromo-2,4,6-trimethylbenzene or 1-bromo-2,4,6-triisopropylbenzene, the expected (E)-1-arylalk-1-en-3-ones were obtained in moderate to good yields. These enones appear to be unstable under the reaction conditions, and the addition of a small amount of hydroquinone to the reaction mixture was found to be crucial, especially for the vinylation of electron-deficient aryl bromides. A variety of alk-1-en-3-ones has been employed, and better results in terms of substrate/catalyst ratios were obtained when oct-1-en-3-one or hex-1-en-3-one was used than when but-1-en-3-one or pent-1-en-3-one was used. It should be noted that several reactions can be performed with as little as 0.1-0.001 mol% catalyst.

  在适当的反应条件下，通过钯催化的alk-1-en-3-ones与芳基溴化物的反应，可以获得高产率的(E)-1-芳基烯-1-烯-3-酮衍生物。铑催化剂中发现四膦配体顺，顺，顺-1,2,3,4-四(二苯膦甲基)环戊烷与[Pd(C3H5)Cl]2结合是一种非常高效的催化剂。通常情况下，电子贫乏的芳基溴化物显示出更高的反应速率，但电子富集的芳基溴化物1-溴-4-(二甲基氨基)苯和4-溴苯甲醚也能导致高产率的芳基化烯酮。即使在空间位阻很大的芳基溴化物如9-溴蒽、1-溴-2,4,6-三甲基苯或1-溴-2,4,6-三异丙基苯的情况下，期望的(E)-1-芳基烯-1-烯-3-酮也能在中等至良好的产率下获得。这些烯酮在反应条件下似乎是不稳定的，在反应混合物中加入少量的氢醌被发现是至关重要的，特别是对于电子缺乏的芳基溴化物的乙烯基化。已使用了多种alk-1-en-3-ones，当使用辛-1-烯-3-酮或己-1-烯-3-酮时，相对于底物/催化剂比例，得到了更好的结果，而不是丁-1-烯-3-酮或戊-1-烯-3-酮。值得注意的是，有几种反应可以在仅0.1-0.001 mol%催化剂的情况下进行。
• Synthesis of (<i>E</i>)-1-Aryl Alk-1-en-3-ones by Tetraphosphine/Palladium-Catalysed Heck Reactions of Alk-1-en-3-ones with Aryl Bromides
  作者：Henri Doucet、Maurice Santelli、Mhamed Lemhadri

  DOI：10.1055/s-2006-948174

  日期：2006.11

  The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(di­phenylphosphinomethyl)cyclopentane in combination with [Pd(C3H5)Cl]2 affords a very efficient catalyst for the Heck reaction of alk-1-en-3-ones with aryl bromides. If appropriate reaction ­conditions are used (NaOAc as base, hydroquinone as stabilising agent and DMF as solvent) high yields of (E)-1-aryl alk-1-en-3-one derivatives are obtained. In general, higher reaction rates were observed with electron-poor aryl bromides, but the electron-rich aryl bromides 4-N,N-dimethylaminobromobenzene and 4-bromoanisole also led to the arylated enones. Even with sterically very congested aryl bromides such as 9-bromoanthracene, 2,4,6-trimethylbromo­benzene or 2,4,6-triisopropylbromobenzene, the expected (E)-1-aryl alk-1-en-3-ones were obtained in moderate to good yields. Moreover, several reactions can be performed with as little as 0.1% catalyst.

  四膦cis,cis,cis-1,2,3,4-四(二苯膦甲基)环戊烷与[Pd(C3H5)Cl]2结合，可以有效地催化烯-1-烯-3-酮与芳基溴化物的赫克反应。如果使用适当的反应条件（以醋酸钠为碱，羟基苯作为稳定剂，DMF作为溶剂），可以获得高产率的（E）-1-芳基烯-1-烯-3-酮衍生物。一般来说，使用电子贫乏的芳基溴化物时反应速率较高，但电子丰富的芳基溴化物4-N,N-二甲基氨基溴苯和4-溴苯醚也能生成芳基化的烯酮。即使是非常拥挤的芳基溴化物，如9-溴芴、2,4,6-三甲基溴苯或2,4,6-三异丙基溴苯，预期的（E）-1-芳基烯-1-烯-3-酮也以中等到良好的产率获得。此外，几乎可以仅用0.1%的催化剂进行多次反应。
• An Improved Procedure for the Claisen-Schmidt Reaction
  作者：J. V. Sinisterra、A. Garcia-Raso、J. A. Cabello、J. M. Marinas

  DOI：10.1055/s-1984-30882

  日期：——
• Nesmejanow; Kotschetkow; Matow, Doklady Akademii Nauk SSSR, 1953, vol. 92, p. 85,87
  作者：Nesmejanow、Kotschetkow、Matow

  DOI：——

  日期：——