2-(hept-2-ynoyl)phenyl acetate | 1403475-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-(hept-2-ynoyl)phenyl acetate
• 英文别名: (2-Hept-2-ynoylphenyl) acetate
• CAS: 1403475-68-2
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: RVUOUNQANCVSQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hept-2-ynoyl)phenyl acetate 在 18-冠醚-6 、 potassium methanolate 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以52%的产率得到2-butyl-4H-chromen-4-one
  参考文献：
  名称：

  使用温和的 Sonogashira 偶联和 18-Crown-6 醚介导的 6-内环化合成黄酮和 γ-苯并吡喃酮

  摘要：

  利用温和的 Sonogashira 偶联和 18-crown-6 醚介导的邻炔基苯乙酸酯的 6-内环化，开发了一种合成黄酮和 γ-苯并吡喃酮的有效方法。通过使用该策略，以令人满意的收率合成了带有给电子基团、卤素和简单烷基取代基的黄酮和γ-苯并吡喃酮。

  DOI：

  10.1002/ejoc.201200529
• 作为产物：
  描述：

  阿司匹林 在 N-甲基吗啉 、 palladium diacetate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 11.0h， 生成 2-(hept-2-ynoyl)phenyl acetate
  参考文献：
  名称：

  Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of “Super-Active Esters”

  摘要：

  A neat palladium-catalyzed alkynylation reaction was developed with "super-active ester" as the carbonyl electrophile, which provides a dean-and efficient synthetic protocol for a broad array Of ynone compounds under CO-, Cu-,, ligand-, and base-free conditions. The superior activity of triazine ester was rationalized by the strong electron;withdrawing ability and the unique affinity of triazine On palladium. A mechanistic experiment clearly demonstrated that the N-Pd coordination of triazine plays a crucial role for the highly efficient C-O activation.

  DOI：

  10.1021/acs.orglett.5b01466

文献信息

• Bifunctional phosphine ligand-enabled gold-catalyzed direct cycloisomerization of alkynyl ketones to 2,5-disubstituted furans
  作者：Xiaojun Hu、Bingwei Zhou、Hongwei Jin、Yunkui Liu、Liming Zhang

  DOI：10.1039/d0cc01238f

  日期：——

  An efficient synthesis of 2,5-disubstituted furans directly from alkynyl ketones has been developed via tandem gold(I)-catalyzed isomerization of alkynyl ketones to allenyl ketones and cycloisomerization. The key to the success of this chemistry is the use of a biphenyl-2-ylphosphine ligand featuring a critical remote tertiary amino group.

  通过串联金（I）催化的炔基酮异构化为烯丙基酮和环异构化，已经开发了直接从炔基酮直接合成2,5-二取代的呋喃的方法。该化学方法成功的关键是使用具有关键远程叔氨基的联苯-2-基膦配体。
• Pd catalyzed couplings of “superactive esters” and terminal alkynes: Application to flavones and γ-benzopyranones construction
  作者：Dandan Yang、Zhenhua Wang、Xiu Wang、Huaming Sun、Zunyuan Xie、Juan Fan、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1016/j.molcata.2016.10.030

  日期：2017.1

  Lewis base, N-methylmorpholine (NMM) accelerated Pd-catalyzed Sonogashira coupling of steric hindered super active esters, la-le, and terminal alkynes. This approach provided an efficient synthetic protocol for a broad array of acylated o-alkynoylphenols compounds, 3a-3e, under moderate conditions. The mechanistic study clearly demonstrated that NNM stabilized the catalytic palladium species, and accelerated the leaving of triazine moiety during the catalytic cycle of the cross-coupling reactions. In addition, piperazine was found to efficiently catalyze the 6-endo cyclization of acylated o-alkynoylphenols, which achieved the diversity oriented synthesis of gamma-benzopyranones, 4aa-4eg, with 93-99% yields. (C) 2016 Elsevier B.V. All rights reserved.
• Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of “Super-Active Esters”
  作者：Bo Yu、Huaming Sun、Zunyuan Xie、Guofang Zhang、Li-Wen Xu、Weiqiang Zhang、Ziwei Gao

  DOI：10.1021/acs.orglett.5b01466

  日期：2015.7.2

  A neat palladium-catalyzed alkynylation reaction was developed with "super-active ester" as the carbonyl electrophile, which provides a dean-and efficient synthetic protocol for a broad array Of ynone compounds under CO-, Cu-,, ligand-, and base-free conditions. The superior activity of triazine ester was rationalized by the strong electron;withdrawing ability and the unique affinity of triazine On palladium. A mechanistic experiment clearly demonstrated that the N-Pd coordination of triazine plays a crucial role for the highly efficient C-O activation.
• Synthesis of Flavones and γ-Benzopyranones Using Mild Sonogashira Coupling and 18-Crown-6 Ether Mediated 6-<i>endo</i>Cyclization
  作者：Da-Wei Chuang、Mohamed El-Shazly、Barve Balaji D.、Yu-Ming Chung、Fang-Rong Chang、Yang-Chang Wu

  DOI：10.1002/ejoc.201200529

  日期：2012.8

  An efficient method for the synthesis of flavones and γ-benzopyranones has been developed utilizing a mild Sonogashira coupling and 18-crown-6 ether mediated 6-endo cyclization of o-alkynoylphenyl acetates. By using this strategy, flavones and γ-benzopyranones bearing electron-donating groups, halogens, and simple alkyl substituents were synthesized in satisfactory yields.

  利用温和的 Sonogashira 偶联和 18-crown-6 醚介导的邻炔基苯乙酸酯的 6-内环化，开发了一种合成黄酮和 γ-苯并吡喃酮的有效方法。通过使用该策略，以令人满意的收率合成了带有给电子基团、卤素和简单烷基取代基的黄酮和γ-苯并吡喃酮。