1-(p-tolyl)pent-1-yn-3-one | 235431-03-5

• 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: 1-(p-tolyl)pent-1-yn-3-one
• 英文别名: 1-(4-Methylphenyl)pent-1-yn-3-one
• CAS: 235431-03-5
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: JMZAPZQSJCYLEB-UHFFFAOYSA-N

物化性质

• 熔点：
  39-40 °C
• 沸点：
  284.1±19.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 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：

  1-(p-tolyl)pent-1-yn-3-one 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 1.0h， 以82%的产率得到1-(4-methylphenyl)-1-pentyn-3-ol
  参考文献：
  名称：

  Enantioselective synthesis of (R)-incrustoporin, an antibiotic isolated from Incrustoporia carneola

  摘要：

  Highly enantiomerically enriched (R)-incrustoporin was enantioselectively synthesized in 43.6% overall yield starting from 4-iodotoluene. The key steps of the synthesis included the asymmetric hydrogenation of 1-(p-tolyl)-1-pentyn-3-one catalyzed by a non-racemic Ru(II) complex and the Pd-catalyzed cyclocarbonylation of so-obtained highly enantiomerically enriched 1-(p-tolyl)-1-pentyn-3-ol. This Pd-catalyzed reaction, whose stereochemical outcome was previously unknown, proceeded with retention of configuration and 2.5% or less racemization. The enantiomeric purities of (R)-1-(p-tolyl)-1-pentyn-3-ol and (R)-incrustoporin were evaluated by HPLC analysis on a Chiralcel OJ column as well as by performing the H-1 NMR spectra of these compounds in a D2O solution which was saturated with alpha- or beta-cyclodextrin, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00085-3
• 作为产物：
  描述：

  丙酸乙酯 、 4-甲苯基乙炔 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以81%的产率得到1-(p-tolyl)pent-1-yn-3-one
  参考文献：
  名称：

  通过将银催化的CO 2掺入共轭的壬烯中而获得四酸

  摘要：

  通过共轭炔酮与二氧化碳的反应，已经成功地实现了对高官能度的四氢苯甲酸的简便且多用途的获取。在碱的存在下，由炔酮生成的烯醇化物通过形成碳-碳键的反应捕获CO 2，伴随着所得羧酸盐与炔烃的5- exo-dig环化反应，并被银催化剂活化。本方法应适用于多种tetronic酸的合成。

  DOI：

  10.1021/acs.orglett.7b01309

文献信息

• Catalytic Ynone–Amidine Formal [4 + 2]-Cycloaddition for the Regioselective Synthesis of Tricyclic Azepines
  作者：T. Prabhakar Reddy、Jagjeet Gujral、Pritam Roy、Dhevalapally B. Ramachary

  DOI：10.1021/acs.orglett.0c03711

  日期：2020.12.18

  A Ca(OTf)2- and self-promoted ynone–amidine atom-economic formal [4 + 2]-cycloaddition of various ynones with amidines is reported for the construction of highly functionalized tricyclic azepines. High reaction rate, ease of operation, and high product selectivity with wide substrate scope are the key advantages of the present annulation protocol.

  报道了一种由Ca（OTf）2-和自我促进的ynone-am原子-经济形式的各种ynone与的正式[4 + 2]-环加成反应，用于构建高度官能化的三环a庚因。高反应速率，易于操作以及在宽范围的基板范围内的高产品选择性是本环法协议的主要优势。
• Solvent free synthesis of ynones using magnetically recoverable Copper-ferrite nanoparticles
  作者：Rituparna Chutia、Bolin Chetia

  DOI：10.1016/j.tetlet.2017.08.063

  日期：2017.10

  A general and efficient biogenic CuFe2O4 MNP's catalyzed synthesis of ynones has been reported for the first time. The reaction occurs in solvent free conditions without the use of any harsh conditions. The average diameter of the nanoparticles was found to be 13.07 nm. The advantages of the protocol include heterogeneous catalysis, easy recyclability of the catalyst and short reaction time. (C) 2017 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of (R)-incrustoporin, an antibiotic isolated from Incrustoporia carneola
  作者：Renzo Rossi、Fabio Bellina、Matteo Biagetti、Luisa Mannina

  DOI：10.1016/s0957-4166(99)00085-3

  日期：1999.3

  Highly enantiomerically enriched (R)-incrustoporin was enantioselectively synthesized in 43.6% overall yield starting from 4-iodotoluene. The key steps of the synthesis included the asymmetric hydrogenation of 1-(p-tolyl)-1-pentyn-3-one catalyzed by a non-racemic Ru(II) complex and the Pd-catalyzed cyclocarbonylation of so-obtained highly enantiomerically enriched 1-(p-tolyl)-1-pentyn-3-ol. This Pd-catalyzed reaction, whose stereochemical outcome was previously unknown, proceeded with retention of configuration and 2.5% or less racemization. The enantiomeric purities of (R)-1-(p-tolyl)-1-pentyn-3-ol and (R)-incrustoporin were evaluated by HPLC analysis on a Chiralcel OJ column as well as by performing the H-1 NMR spectra of these compounds in a D2O solution which was saturated with alpha- or beta-cyclodextrin, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Access to Tetronic Acids via Silver-Catalyzed CO₂ Incorporation into Conjugated Ynones
  作者：Yuta Sadamitsu、Keiichi Komatsuki、Kodai Saito、Tohru Yamada

  DOI：10.1021/acs.orglett.7b01309

  日期：2017.6.16

  versatile access to highly functionalized tetronic acids has been successfully achieved through the reaction of conjugated ynones with carbon dioxide. In the presence of a base, the enolates generated from the ynones capture CO2 via a carbon–carbon bond-forming reaction, accompanied by a 5-exo-dig cyclization reaction of the resulting carboxylate to the alkyne, activated by a silver catalyst. The present

  通过共轭炔酮与二氧化碳的反应，已经成功地实现了对高官能度的四氢苯甲酸的简便且多用途的获取。在碱的存在下，由炔酮生成的烯醇化物通过形成碳-碳键的反应捕获CO 2，伴随着所得羧酸盐与炔烃的5- exo-dig环化反应，并被银催化剂活化。本方法应适用于多种tetronic酸的合成。