2-苯基-1-丁烯-1-酮 | 20452-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-苯基-1-丁烯-1-酮
• 英文名称: phenylethylketene
• 英文别名: ethylphenylketene；2-phenyl-but-1-en-1-one；Phenylethylketen；Aethyl-phenyl-keten；Ethyl-phenyl-keten；1-Buten-1-one, 2-phenyl-
• CAS: 20452-67-9
• 化学式: C₁₀H₁₀O
• 分子量: 146.189
• InChiKey: GFVFSRZJKWODDS-UHFFFAOYSA-N

物化性质

• 沸点：
  198.1±10.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914399090

反应信息

• 作为反应物：
  描述：

  2-苯基-1-丁烯-1-酮 在 sodium hydroxide 作用下， 生成 2-苯基丁酸
  参考文献：
  名称：

  Solvent isotope effect on the hydroxide-ion-catalyzed hydration of ketenes in aqueous solution

  摘要：

  Five ketenes, phenyl(ethyl)ketene, phenyl(methylthio)ketene, diphenylketene, pentafluorophenylketene, and 1-naphthylketene, were generated flash photolytically and solvent isotope effects (H2O vs. D2O) on their hydroxide-ion-catalyzed hydration in aqueous solution were determined. The values obtained are all weakly inverse and closely similar (k(HO)/k(DO) = 0.76-0.97), as expected for these fast, hydroxide-ion-consuming reactions, known to proceed by nucleophilic attack of hydroxide on the ketene carbonyl group. The characteristic magnitude of these isotope effects should prove useful in identifying new examples of this reaction.

  DOI：

  10.1139/cjc-77-4-459
• 作为产物：
  描述：

  2-苯基丁酸 在 氯化亚砜 、 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 12.0h， 生成 2-苯基-1-丁烯-1-酮
  参考文献：
  名称：

  NHC促进立体异构和化学扩散的芳烷基烯酮与氯的官能化

  摘要：

  用N-杂环卡宾处理烷基芳基烯酮和三氯乙醛（氯代）时，观察到立体和化学发散对映选择性反应途径，选择性地产生β-内酯（高达88:12 dr，高达94％  ee）或α-氯代酯（高达至94％  ee）。乙烯酮中的2-芳基取代或α-支链的i Pr烷基取代基都有利于氯化途径，从而使氯醛可以在不对称催化中用作亲电子氯化试剂。

  DOI：

  10.1002/chem.201503308

文献信息

• Palladium complex catalyzed synthesis of α,β-unsaturated ketones from alkylphenylketene and aroyl chloride
  作者：Take-aki Mitsudo、Mamoru Kadokura、Yoshihisa Watanabe

  DOI：10.1016/s0040-4039(00)98886-5

  日期：1985.1

  α,β-Unsaturated ketones were obtained from alkylphenylketene and aroyl chloride via decarbonylation reaction in the presence of catalytic amounts of tetrakis(triphenylphosphine) palladium.

  在催化量的四（三苯基膦）钯存在下，通过脱羰反应从烷基苯乙烯酮和芳酰氯获得α，β-不饱和酮。
• An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations
  作者：Edward Richmond、Kenneth B. Ling、Nicolas Duguet、Lois B. Manton、Nihan Çelebi-Ölçüm、Yu-Hong Lam、Sezen Alsancak、Alexandra M. Z. Slawin、K. N. Houk、Andrew D. Smith

  DOI：10.1039/c4ob02526a

  日期：——

  The reaction of l-serine derived N-arylnitrones with alkylarylketenes generates 3-alkyl-3-aryloxindoles in good yields and excellent enantioselectivities.

  <sc>l</sc>-丝氨酸衍生的<italic>N</italic>-芳基腈与烷基芳基酮烯反应，以高收率和极好的对映选择性生成3-烷基-3-芳氧吲哚。

• Formal [3+2] Cycloaddition of Ketenes and Oxaziridines Catalyzed by Chiral Lewis Bases: Enantioselective Synthesis of Oxazolin-4-ones
  作者：Pan-Lin Shao、Xiang-Yu Chen、Song Ye

  DOI：10.1002/anie.201003532

  日期：2010.11.2

  Choose the right cat.: A highly enantioselective synthesis of oxazolin‐4‐ones by the formal [3+2] cycloaddition of ketenes and a racemic oxaziridines has been developed (see scheme; cat.=N‐heterocyclic carbenes for disubstituted ketenes or cinchona alkaloids for monosubstituted ketenes, Ts=4‐toluenesulfonyl).

  选择合适的猫。：已开发出通过对烯酮的正式[3 + 2]环加成和外消旋的恶氮丙啶进行高度对映选择性的恶唑啉-4-酮的合成（参见方案； cat。= N-杂环卡宾用于双取代的烯酮，或金鸡纳生物碱用于单取代的酮， Ts = 4-甲苯磺酰基）。
• Diethyl zinc catalyzed diastereoselective addition of ketenes to (S)-(+)-3-hydroxytetrahydrofuran
  作者：Vishnu K. Tandon

  DOI：10.1016/s0040-4039(01)01164-9

  日期：2001.8

  The reaction of (S)-(+)-3-hydroxytetrahydrofuran with phenyl methyl ketene in presence of n-BuLi and Et2Zn results in the formation of the diastereomeric esters (SS+SR) with a high degree of diastereoselectivity (98:2).

  （S）-（+）-3-羟基四氢呋喃在n -BuLi和Et 2 Zn存在下与苯基甲基乙烯酮的反应导致形成非对映体酯（SS + SR），具有高度非对映选择性（98： 2）。
• Aluminum complexes incorporating symmetrical and asymmetrical tridentate pincer type pyrrolyl ligands: synthesis, characterization and reactivity study
  作者：Pei-Hsin Liu、Fu-Jung Chuang、Cheng-Yi Tu、Ching-Han Hu、Tzu-Wei Lin、Yu-Tang Wang、Chia-Her Lin、Amitabha Datta、Jui-Hsien Huang

  DOI：10.1039/c3dt51133b

  日期：——

  A series of aluminum complexes incorporating substituted symmetrical and asymmetrical tridentate pyrrolyl ligands are synthesized conveniently and the treatment of the derivatives with small organic molecules are analyzed. The reaction of lithiated [C4H2NH(2-CH2NHtBu)(5-CH2NR1R2)], where for 1, R1 = R2 = Me; 2, R1 = H, R2 = tBu, with AlCl3 in diethyl ether affords Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)]Cl2 (3) and Al[C4H2N(2,5-CH2NHtBu)2]Cl2 (4), respectively, in high yields. Furthermore, subjecting 3 and 4 to reaction with one equiv. of LiNMePh in diethyl ether generates Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)][NMePh]Cl (5) and Al[C4H2N(2,5-CH2NHtBu)2][NMePh]Cl (6), respectively, while eliminating one equiv. of LiCl. The reaction between compound 4 with two equiv. of LiO-Ph-4-Me in diethyl ether yields the aluminum di-phenoxide compound Al[C4H2N(2,5-CH2NHtBu)2](O-Ph-4-Me)2 (7) whereas the combination of 3 and two equiv. of LiNHtBu, produces Al[C4H2N(2-CH2NtBu)(5-CH2NMe2)](NHtBu)(NH2tBu) (8). Additionally, the mixing of 1 and one equiv. of AlMe3 renders Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)]Me2 (9). Adding one more equiv. of AlMe3 with 9 affords Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)AlMe3]Me2} (10), which can also be obtained by treating 1 with two equiv. of AlMe3 directly. The treatment of 9 with one equiv. of 2,6-dimethylphenol in diethyl ether gives the aluminum alkoxide derivative, Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)](O-C6H3-2,6-Me2)Me (11). Furthermore, the reaction between 9 and one equiv. of 1-ethyl-1-phenyl ketene, initiates the aluminum dimethyl complex AlC4H2N[2-CH2CEtPh-C(O)-NHtBu](5-CH2NMe2)}Me2 (12) with a C–N bond breakage and a C–C bond formation. All the Al-derivatives are characterized by 1H and 13C NMR spectroscopy and the molecular structures are determined by single crystal X-ray diffractometry in solid state.

  一系列包含取代对称和非对称三齿吡咯烷配体的铝配合物被方便地合成,其与小有机分子的反应被分析。在二乙醚中,与AlCl3反应,lithiated [C4H2NH(2-CH2NHtBu)(5-CH2NR1R2)]分别高产率地生成Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)]Cl2(3)和Al[C4H2N(2,5-CH2NHtBu)2]Cl2(4),其中1, R1 = R2 = Me;2, R1 = H, R2 = tBu。此外,在二乙醚中,3和4分别与一份当量的LiNMePh反应,生成Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)][NMePh]Cl(5)和Al[C4H2N(2,5-CH2NHtBu)2][NMePh]Cl(6),同时释放一份当量的LiCl。4与两份当量的LiO-Ph-4-Me在二乙醚中反应生成双苯氧基铝化合物Al[C4H2N(2,5-CH2NHtBu)2](O-Ph-4-Me)2(7),而3与两份当量的LiNHtBu反应生成Al[C4H2N(2-CH2NtBu)(5-CH2NMe2)](NHtBu)(NH2tBu)(8)。此外,1与一份当量的AlMe3混合生成Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)]Me2(9)。9再与一份当量的AlMe3反应生成Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)AlMe3]Me2}(10),这也可以通过1与两份当量的AlMe3直接反应得到。9与一份当量的2,6-二甲基苯酚在二乙醚中反应生成铝醇盐衍生物Al[C4H2N(2-CH2NHtBu)(5-CH2NMe2)](O-C6H3-2,6-Me2)Me(11)。此外,9与一份当量的1-乙基-1-苯基乙烯酮反应,引发铝二甲基配合物AlC4H2N[2-CH2CEtPh-C(O)-NHtBu](5-CH2NMe2)}Me2(12)的生成,伴随着C-N键的断裂和C-C键的形成。所有铝衍生物通过1H和13C NMR谱表征,分子结构通过单晶X射线衍射法在固态中测定。

表征谱图