(E)-1-phenyloct-1-en-3-one | 29478-39-5

• 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-phenyloct-1-en-3-one
• 英文别名: (E)-1-phenyl-1-octen-3-one；(1E)-1-phenyl-1-octen-3-one
• CAS: 29478-39-5
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: WDAQVRGVKLLSHT-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (E)-1-phenyloct-1-en-3-one 在 氨 、 镍 作用下， 生成 1-苯基-3-辛醇
  参考文献：
  名称：

  Metayer, Recueil des Travaux Chimiques des Pays-Bas, 1952, vol. 71, p. 153,156

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-1-苯基-2-丙炔-1-醇 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 (E)-1-phenyloct-1-en-3-one
  参考文献：
  名称：

  Formation of .alpha.,.beta.-unsaturated ketones from the gas-phase pyrolysis of .alpha.-substituted propargyl esters

  摘要：

  DOI：

  10.1021/ja00846a036

文献信息

• Mizoroki–Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C–C Bond Olefination
  作者：Mei-Ling Wang、Hui Xu、Han-Yuan Li、Biao Ma、Zhen-Yu Wang、Xing Wang、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.1c00296

  日期：2021.3.19

  Mizoroki–Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C–C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility

  未应变的芳基酮与丙烯酸酯/苯乙烯的Mizoroki-Heck反应是通过钯催化的配体促进的C-C键裂解实现的。各种（杂）芳基酮在反应中是相容的，从而以良好至优异的产率提供了烯烃产物。在某些药物，天然产物和香料衍生的芳基酮的后期烯烃聚合中的进一步应用证明了该方案的合成效用。通过采用酮作为导向基团和离去基团二者，1,2- bifunctionalization经由顺序实现邻-C-H的烷基化/本位-Heck烯。
• 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。
• FLAVOR MODULATOR HAVING PYRIDINE DERIVATIVE OR SALT THEREOF AS ACTIVE INGREDIENT
  申请人：T. HASEGAWA CO., LTD.

  公开号：US20180072670A1

  公开（公告）日：2018-03-15

  2-(phenylalkyloxyalkyl)pyridine derivative or a 2-(phenylalkylthioalkyl)pyridine derivative imparts, when added to food and drink or cosmetics as an active ingredient, a flavor of natural impression thereto; and in particular, when added to food and drink, the compound imparts an umami imparting or enhancing, a saltiness enhancing a sweetness enhancing, and in particular, when added to a milk or dairy product, a food or drink product containing a milk or dairy product, or a dairy replacement product, the compound provides a milk richness enhancing.

  2-(苯基烷氧基烷基)吡啶衍生物或2-(苯基烷硫基烷基)吡啶衍生物，当作为食品、饮料或化妆品的活性成分添加时，赋予其一种天然印象的风味；特别是当添加到食品和饮料中时，该化合物赋予了一种鲜味、增强了咸味和甜味，特别是当添加到牛奶或乳制品中时，该化合物提供了增强奶香的效果。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• Oxygenation of Simple Olefins through Selective Allylic C−C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes
  作者：Jianzhong Liu、Xiaojin Wen、Chong Qin、Xinyao Li、Xiao Luo、Ao Sun、Bencong Zhu、Song Song、Ning Jiao

  DOI：10.1002/anie.201705671

  日期：2017.9.18

  allylic C−C σ‐bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2‐Aryl or alkyl migration through allylic C−C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O‐atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal‐free

  据报道，一种新颖的不含金属的烯丙基CCσ键裂解简单的烯烃可得到有价值的肉桂醛。1,2-芳基或烷基迁移通过烯丙基C-C键断裂在此转化过程中发生，这需要烷基叠氮化物试剂的协助。这种方法可以使O-atom掺入简单的未官能化烯烃中，以构建肉桂醛。该反应具有简单的烃底物，无金属条件以及高区域选择性和立体选择性。