2-(3-phenylpropioloyl)phenyl acetate | 16619-67-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(3-phenylpropioloyl)phenyl acetate
• 英文别名: 2-(3-phenylprop-2-ynoyl)phenyl acetate；[2-(3-Phenylprop-2-ynoyl)phenyl] acetate
• CAS: 16619-67-3
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: RJLIWFVZAWXRCX-UHFFFAOYSA-N

物化性质

• 沸点：
  421.8±47.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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-(3-phenylpropioloyl)phenyl acetate 在 9-氮杂久洛尼定 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以38%的产率得到3-acetyl-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  通过路易斯碱9-azazulolidine催化的串联酰基转移环化反应合成3-芳基黄酮。

  摘要：

  开发了路易斯碱催化导致3-芳基黄酮的酰化的邻炔基酚的串联酰基转移环化。9-氮杂唑烷在环境温度下平稳地促进了芳酰基衍生物的反应，并且以中等至优异的产率实现了具有不同取代基的3-芳酰基黄酮的结构多样的合成。

  DOI：

  10.1039/c2cc37015h
• 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-(3-phenylpropioloyl)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

• Highly Selective and Modular Synthesis of 3-Aryl-4-(arylethynyl)-2<i>H</i>-chromen-2-ones from 2-Iodoaryl 2-Arylacetates through a Carbonylative Sonogashira Coupling-Intramolecular Aldol Cascade Reaction
  作者：Attoor Chandrasekhar、Venkatachalam Ramkumar、Sethuraman Sankararaman

  DOI：10.1002/ejoc.201600569

  日期：2016.8

  H-chromen-2-ones from 2-iodoaryl 2-arylacetates and arylacetylenes has been developed. The carbonylative Sonogashira coupling–intramolecular aldol casade reaction was carried out in the presence of Pd(PPh3)2(Cl)2 as the catalyst. The one-pot approach that involves the in situ formation of the 2-iodoaryl 2-arylacetates from the corresponding 2-iodophenols and 2-arylacetyl chlorides followed by the palladium-catalyzed

  已经开发了一种用于从 2-iodoaryl 2-arylacetates 和芳基乙炔合成 3-aryl-4-(arylethynyl)-2H-chromen-2-ones 的模块化方法。在 Pd(PPh3)2(Cl)2 作为催化剂存在下，进行了羰基化 Sonogashira 偶联-分子内醇醛级联反应。一锅法包括从相应的 2-碘苯酚和 2-芳基乙酰氯原位形成 2-碘芳基乙酸酯，然后在芳基乙炔存在下钯催化的羰基化环化也已被描述为3-芳基-4-(芳基乙炔基)-2H-色烯-2-酮的形成。
• 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。
• Electronic and steric effects of substituents in 1,3-diphenylprop-2-yn-1-one during its reaction with Ru₃(CO)₁₂
  作者：Lei Xu、Shasha Li、Liping Jiang、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1039/c7ra13626a

  日期：——

  reaction of Ru3(CO)12 with alkynyl ketones PhCCC(O)R (RPh (1); 2-Cl-Ph (2); 4-NO2-Ph (3); 2-NH2-Ph (4); and 2-CH3COO-Ph (5)) proceeds in toluene with the formation of Ru3(CO)9(μ-CO)(η4-triruthenium) derivatives (1a–5a), Ru(CO)3(η4-ruthenole) derivatives (1b–4b, 1c–5c and 4d) and cyclotrimerization products (1e–2e and 1f–3f). Compounds 1a–5a were isolated from the reaction of Ru3(CO)12 with one equivalent

  Ru 3（CO）12与炔酮PhC CC（O）R（R Ph（1）; 2-Cl-Ph（2）; 4-NO 2 -Ph（3）; 2-NH 2 -Ph的热反应（4）;和2-CH 3 COO-PH（5在甲苯中））进行与钌形成3（CO）9（μ-CO）（η 4 -triruthenium）衍生物（1A-5A），钌（CO ）3（η 4 -ruthenole）衍生物（1B-4B，1C-5C和图4d）和环三聚产物（1e–2e和1f–3f）。从Ru 3（CO）12与一当量的1-5的反应中分别分离出化合物1a-5a。Ruthenoles 1B-3B和1C-3C通过加入收集1-3到对应的1A-3A在1的摩尔比：1.环三聚产物1E-2E和1F-3F获得当1-3加入到它们相应的分别为1b–2b和1c–3c。4b，4c和4d的反应过程中，得到4与4a中，但只有5C的在反应过程中，收集5与5a中。所有化合物均通过NMR，FT
• 采用乙酰氧基保护的炔酮制备苯并吡喃酮类 化合物的方法
  申请人：陕西师范大学

  公开号：CN105175375B

  公开（公告）日：2017-07-11

  本发明公开了一种采用乙酰氧基保护的炔酮制备苯并吡喃酮类化合物的方法，该方法以哌嗪为催化剂，将乙酰氧基保护的炔酮类化合物在室温条件下直接发生关环反应生成苯并吡喃酮类化合物。本发明操作简单，无需添加配体，催化剂廉价、用量少、对空气和水稳定，反应条件温和，反应时间短，成本较低，原子经济性高，底物适用性广，目标产物后处理简单且产率高，可广泛用于天然产物苯并吡喃酮类化合物的制备。
• 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.