3-甲基-1-苯基戊-4-烯-2-酮 | 135987-22-3

• 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: 3-甲基-1-苯基戊-4-烯-2-酮
• 英文名称: 3-methyl-1-phenyl-4-penten-2-one
• 英文别名: 4-Penten-2-one, 3-methyl-1-phenyl-；3-methyl-1-phenylpent-4-en-2-one
• CAS: 135987-22-3
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: BXKSELGVDYGQSR-UHFFFAOYSA-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

• 作为反应物：
  描述：

  3-甲基-1-苯基戊-4-烯-2-酮 在 N-甲基吗啉 、 四氧化锇 、 对甲苯磺酸 作用下， 生成 2-benzyl-3-methylfuran
  参考文献：
  名称：

  A Practical Synthesis of Rosefuran. Furans from Acetylenes and Allyl Alcohols

  摘要：

  A new atom-economical synthetic strategy for the synthesis of furans emerges from beta,gamma-unsaturated ketones which are readily available from acetylenes and allyl alcohols by simple additions in the presence of a ruthenium catalyst. Dihydroxylation using catalytic osmium tetraoxide creates a diol that is remarkably prone to cyclize to furans in the presence of an acid catalyst. The novelty of this synthesis lies in the overall strategy whereby furans are available in two steps from allyl alcohols and acetylenes with only water as the byproduct. A straightforward synthesis of the prized fragrance of oil of rose, rosefuran, from propargyl bromide, acetone, and 1-buten-3-ol in 23% overall yield illustrates the utility of this new strategy.

  DOI：

  10.1021/jo00084a026
• 作为产物：
  描述：

  3-丁烯-2-醇 、 苯乙炔 在 二(三苯基膦)环戊二烯基氯化钌(II) ammonium hexafluorophosphate 作用下， 反应 8.0h， 以68%的产率得到3-甲基-1-苯基戊-4-烯-2-酮
  参考文献：
  名称：

  A Practical Synthesis of Rosefuran. Furans from Acetylenes and Allyl Alcohols

  摘要：

  A new atom-economical synthetic strategy for the synthesis of furans emerges from beta,gamma-unsaturated ketones which are readily available from acetylenes and allyl alcohols by simple additions in the presence of a ruthenium catalyst. Dihydroxylation using catalytic osmium tetraoxide creates a diol that is remarkably prone to cyclize to furans in the presence of an acid catalyst. The novelty of this synthesis lies in the overall strategy whereby furans are available in two steps from allyl alcohols and acetylenes with only water as the byproduct. A straightforward synthesis of the prized fragrance of oil of rose, rosefuran, from propargyl bromide, acetone, and 1-buten-3-ol in 23% overall yield illustrates the utility of this new strategy.

  DOI：

  10.1021/jo00084a026

文献信息

• Allylation of Aldehydes by Allyl- and Crotyltributyltin in the Presence of Catalytic Amounts of Bu₂SnCl₂Complex
  作者：Katsunori Yano、Akio Baba、Haruo Matsuda

  DOI：10.1246/bcsj.65.66

  日期：1992.1

  In nearly neutral media, the reaction of allylic tributyltin with aldehydes is effectively catalyzed by Bu2SnCl2 complexes. The addition of coordinative reagents and benzoyl chloride as a quencher is required of the catalytic allylation, furnishing homoallyl benzoates in good to excellent yields, where a regioreversed coupling to conventional methods using crotyltributyltin is exclusively observed.

  在接近中性的介质中，烯丙基三丁基锡与醛的反应可由 Bu2SnCl2 复合物有效催化。催化烯丙基化反应时需要加入配位试剂和苯甲酰氯作为淬灭剂，以良好到极佳的产率获得均烯丙基苯甲酸酯，与使用巴豆三丁基锡的传统方法相比，这种反应只出现了逆向偶联。
• Indium in organic synthesis: Convenient synthesis of β,γ-unsaturated ketones
  作者：J.S. Yadav、Dale Srinivas、Gondi Sudershan Reddy、Konuru Hima Bindu

  DOI：10.1016/s0040-4039(97)10341-0

  日期：1997.12

  A mild and efficient method for the preparation of β,γ unsaturated ketones by a simple reaction on acid chloride with allyl, crotyl, prenyl bromide and indium in DMF is described.

  描述了一种温和而有效的方法，该方法通过在酰氯上与DMF中的烯丙基，巴豆基，异戊烯基溴化物和铟进行简单反应来制备β，γ不饱和酮。
• Enantioconvergent Palladium‐Catalyzed Alkylation of Tertiary Allylic C−H Bonds
  作者：Zhong‐Sheng Nong、Xin‐Ran Chen、Pu‐Sheng Wang、Xin Hong、Liu‐Zhu Gong

  DOI：10.1002/anie.202312547

  日期：2023.11.13

  phosphoramidite-catalyzed intermolecular enantioconvergent alkylation of racemic tertiary allylic C−H bonds provides facile access to a range of enantioenriched allylic compounds featuring quaternary carbon stereocenters. The deracemization has been accomplished through a rate-limiting cleavage of racemic tertiary allylic C−H bonds to generate σ-allyl-Pd species, and the obtained E/Z-selectivity of σ-allyl-Pd species

  Pd-手性亚磷酰胺催化的外消旋叔烯丙基 C-H 键的分子间对映会聚烷基化可以方便地获得一系列具有季碳立构中心的对映体富集的烯丙基化合物。去消旋化是通过外消旋叔烯丙基 C−H 键的限速裂解生成 σ-烯丙基-Pd 物质来完成的，并且所获得的σ-烯丙基-Pd 物质的E/Z选择性通过亲核试剂显着调节非对映选择性协调启用的 S N 2′-烯丙基化途径。
• Studies of the synthetic applications of element-organic compounds of 15th and 16th Groups. 97. Pentaorganylstiborane. 2. Reactions of pentaorganylstiboranes with acyl chlorides and ketones
  作者：Lijun Zhang、Yaozeng Huang、Hongxia Jiang、Duanmu Jun、Yi Liao

  DOI：10.1021/jo00028a075

  日期：1992.1
• Synthesis of allyl ketone via Lewis acid promoted Barbier-type reaction
  作者：Adam Shih-Yuan Lee、Li-Shin Lin

  DOI：10.1016/s0040-4039(00)01446-5

  日期：2000.11