2-methyl-1-phenylbut-2-en-1-one | 19847-64-4

• 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-methyl-1-phenylbut-2-en-1-one
• 英文别名: 2-methyl-1-phenyl-but-2-en-1-one；2-Methyl-1-phenyl-but-2-en-1-on；α-Oxo-β-methyl-α-phenyl-β-butylen；(α-Methyl-propenyl)-phenyl-keton；α-Aethyliden-propiophenon；Phenyl 1,2-dimethylvinyl ketone
• CAS: 19847-64-4
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: AXOYGHVXGWFROM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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-methyl-1-phenylbut-2-en-1-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 、 (2R,3R)-2,3-dihydroxy-2-methyl-1-phenylbutan-1-one
  参考文献：
  名称：

  一类用于植物诱导抗性的化合物及其使用方法

  摘要：

  本发明公开了一类用于植物诱导抗性的化合物及其使用方法，该化合物通式如式(I)所示，其中R基团的意义见说明书。本发明公开的化合物具有很好的稳定性和水溶性，并表现出优异的诱导植物抗病活性，在农业上有很好的使用价值。

  公开号：

  CN108569997A
• 作为产物：
  描述：

  1-phenyl-2-methyl-3-dimethylamino-2-propen-1-one 在 甲基碘化镁 、 乙醚 作用下， 生成 2-methyl-1-phenylbut-2-en-1-one
  参考文献：
  名称：

  Cyclopropanes. I. The Reaction between Nitrocyclopropyl Ketones and Alkali

  摘要：

  DOI：

  10.1021/ja01176a021

文献信息

• Alkynes as Allylmetal Equivalents in Redox-Triggered C–C Couplings to Primary Alcohols: (<i>Z</i>)-Homoallylic Alcohols via Ruthenium-Catalyzed Propargyl C–H Oxidative Addition
  作者：Boyoung Y. Park、Khoa D. Nguyen、Mani Raj Chaulagain、Venukrishnan Komanduri、Michael J. Krische

  DOI：10.1021/ja505962w

  日期：2014.8.27

  The cationic ruthenium catalyst generated upon the acid–base reaction of H2Ru(CO)(PPh3)3 and 2,4,6-(2-Pr)3PhSO3H promotes the redox-triggered C–C coupling of 2-alkynes and primary alcohols to form (Z)-homoallylic alcohols with good to complete control of olefin geometry. Deuterium labeling studies, which reveal roughly equal isotopic compositions at the allylic and distal vinylic positions, along with

  H2Ru(CO)(PPh3)3 和 2,4,6-(2-Pr)3PhSO3H 酸碱反应生成的阳离子钌催化剂促进氧化还原引发的 2-炔烃和伯醇的 C-C 偶联形成 (Z)-高烯丙醇，对烯烃几何形状有良好的完全控制。氘标记研究揭示了烯丙基和远端乙烯基位置的同位素组成大致相同，以及其他数据，证实了涉及钌 (0) 介导的丙二烯-醛氧化偶联形成瞬态氧杂环丁烯环的催化机制，这一事件最终定义了(Z)-烯烃立体化学。
• Taming a Vinyl Cation with a Simple Al(OTf)₃Catalyst To Promote C−C Bond Cleavage
  作者：Meike Niggemann、Liang Fu、Helena Damsen

  DOI：10.1002/chem.201700282

  日期：2017.9.7

  the aluminum catalyst to the rearranging species, which is encouraged by a reversible background reaction. This participation of the catalyst beyond the ionization step is unique in the realm of carbocation driven reactions and opens up the possibility of a catalyst‐induced chiral induction in the future. Furthermore, the study represents a rare example of detailed mechanistic analysis of a reaction

  详细的机械研究确定了1,3-芳基转移的逐步性质，这使我们最近公开的Al 3+催化将未活化的炔烃插入sp 2 –sp 3苯甲醇的CC键。发现对于重排产物的选择性是由于铝催化剂与重排物质的持续配位而引起的，这是由于可逆的背景反应而引起的。催化剂在电离步骤之外的参与在碳正离子驱动的反应领域中是独一无二的，并为将来引发催化剂诱导的手性诱导开辟了可能性。此外，该研究代表了对反应进行详细机械分析的罕见例子，该反应的产物选择性随转化率的增加而变化。
• Preparation of .alpha.,.beta.-unsaturated carbonyl compounds
  申请人：BASF Aktiengesellschaft

  公开号：US05169958A1

  公开（公告）日：1992-12-08

  A process for the preparation of .alpha.,.beta.-unsaturated carbonyl compounds of the formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy or aryloxy, R.sup.2 is aryl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen and R.sup.3 is tetrahydrofuranyl or aryl which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen, which comprises reacting 3-amino-2-propen-1-ones of the formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, and R.sup.4 and R.sup.5 are, independently of one another, hydrogen, C.sub.1 -C.sub.10 -alkyl or aryl, with a magnesium halide of the formula III R.sup.3 --Mg--Y (III) where Y is halogen, at from -20.degree. to 100.degree. C., and novel .alpha.,.beta.-unsaturated carbonyl compounds and novel 3-amino-2-propen-1-ones are described.

  一种制备式I的α，β-不饱和羰基化合物的方法，其中R1是氢，C1-C10-烷基，C1-C10-烷氧基或芳氧基，R2是苯基，未取代或被C1-C4-烷基，C1-C4-烷氧基，三氟甲基和/或卤素取代，R3是四氢呋喃基或芳基，被C1-C4-烷基，C1-C4-烷氧基，三氟甲基和/或卤素取代，包括将式II的3-氨基-2-丙烯-1-酮与式III的镁卤化物反应，其中R1，R2和R3具有上述含义，R4和R5分别是氢，C1-C10-烷基或芳基，反应温度在-20℃至100℃之间，描述了新的α，β-不饱和羰基化合物和新的3-氨基-2-丙烯-1-酮。
• Iron‐Catalyzed Oxyphosphorylation of Styrenes to Access <i>β</i>‐Ketophosphonates and <i>α</i>, <i>β</i>‐Unsaturated Ketones
  作者：Yukun Zhao、Jingwen Xu、Hongbing Chen、Yi Xia、Lin Hu

  DOI：10.1002/adsc.202300733

  日期：2023.10.13

  developed, which generates a range of previously underexplored α-substituted β-ketophosphonates in 55~70% yields. Furthermore, a convenient one-pot procedure by direct conversion of styrenes to α, β-unsaturated ketones is also developed based on the new catalytic reactions, thus offering a protocol to access two classes of valuable products from simple starting materials.

  开发了第一个在露天条件下铁催化苯乙烯衍生物与 H-膦酸二烷基酯的氧代磷酸化反应，生成了一系列先前未充分开发的 α-取代的β-酮膦酸酯，产率 55~70%。此外，基于新的催化反应，还开发了一种方便的一锅法，将苯乙烯直接转化为α，β-不饱和酮，从而提供了一种从简单的起始原料获得两类有价值的产品的方案。
• Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism
  作者：Javed Iqbal、Rajiv Ranjan Srivastava

  DOI：10.1021/jo00033a020

  日期：1992.3

  Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield. Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones. Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate. The beta-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting beta-acetoxy carbonyl compound is observed. A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene. A mechanism for these acylations is proposed by invoking an electron-transfer process.