2-butyl-4H-chromen-4-one | 57262-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-butyl-4H-chromen-4-one
• 英文别名: 2-n-butyl-chromone；2-Butyl-chromen-4-one；2-butylchromen-4-one
• CAS: 57262-51-8
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: GFYDJUNUQDZRFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-butyl-4H-chromen-4-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以92%的产率得到2-butyl-4H-1-benzopyran-4-thione
  参考文献：
  名称：

  Milewski; Urjasz; Maciejewski, Polish Journal of Chemistry, 1998, vol. 72, # 11, p. 2405 - 2417

  摘要：

  DOI：
• 作为产物：
  描述：

  邻乙酰水杨酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 18-冠醚-6 、 potassium methanolate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 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

文献信息

• Pd-Catalyzed Copper-Free Carbonylative Sonogashira Reaction of Aryl Iodides with Alkynes for the Synthesis of Alkynyl Ketones and Flavones by Using Water as a Solvent
  作者：Bo Liang、Mengwei Huang、Zejin You、Zhengchang Xiong、Kui Lu、Reza Fathi、Jiahua Chen、Zhen Yang

  DOI：10.1021/jo050498t

  日期：2005.7.1

  Pd-catalyzed copper-free carbonylative Sonogashira coupling reaction to synthesize alkynyl ketones from terminal alkynes and aryl iodides was achieved by using water as a solvent. The reaction was carried out at room temperature under balloon pressure of CO with Et3N as a base. The developed method was successfully applied to the synthesis of flavones.

  钯催化的无铜羰基化Sonogashira偶联反应，是通过用水为溶剂，由末端炔烃和芳基碘化物合成炔基酮的。反应在室温下以Et 3 N为碱在CO的球囊压力下进行。所开发的方法已成功地应用于黄酮的合成。
• Highly efficient synthesis of flavones via Pd/C-catalyzed cyclocarbonylation of 2-iodophenol with terminal acetylenes
  作者：Fengxiang Zhu、Yahui Li、Zechao Wang、Xiao-Feng Wu

  DOI：10.1039/c6cy00613b

  日期：——

  A highly efficient and selective Pd/C-catalyzed ligand-free cyclocarbonylation reaction for the synthesis of flavones has been developed. Various flavone derivatives were isolated in excellent yields with excellent functional group tolerances. Additionally, catalyst reuse experiments were performed successfully as well.

  已经开发出用于黄酮合成的高效且选择性的Pd / C催化的无配体环羰基化反应。以优异的产率和优异的官能团耐受性分离出各种黄酮衍生物。另外，催化剂再利用实验也成功进行。
• Pd–carbene catalyzed carbonylation reactions of aryl iodides
  作者：Liqin Xue、Lijun Shi、Yuan Han、Chungu Xia、Han Vinh Huynh、Fuwei Li

  DOI：10.1039/c1dt10433k

  日期：——

  A series of carbene complexes [PdBr2(iPr2-bimy)L] (C2–C13) with different types of co-ligands (L) have been tested for their catalytic activities in the carbonylative annulation of 2-iodophenol with phenylacetylene in DMF to afford the respective flavone 2a. Complex C12 with an N-phenylimidazole co-ligand showed the best activity and also afforded high yields when the substrate scope was extended to other aryl or pyridyl acetylenes. In addition, catalyst C12 was also efficient in the carbonylative annulation of 2-iodoaniline with acid chlorides giving the desirable 2-substituted 4H-3,1-benzoxazin-4-ones (4) in good yields. Additionally, this Pd–NHC complex also proved to be a very efficient catalyst for the hydroxycarbonylation of iodobenzene derivatives at low catalyst loading and under low CO pressure. These results demonstrate the versatility and efficiency of this phosphine-free Pd(II)–NHC complex in different types of carbonylations of aryl iodides under mild conditions.

  一系列含有不同类型配体（L）的卡宾配合物[PdBr2(iPr2-bimy)L]（C2至C13）被测试其在二甲基甲酰胺（DMF）中催化2-碘苯酚与苯乙炔进行羰基化环化反应的活性，以制备相应的黄酮2a。含有N-苯基咪唑配体的配合物C12显示出最佳活性，并且在将底物范围扩展到其他芳基或吡啶乙炔时也能获得高产率。此外，催化剂C12在催化2-碘苯胺与酰氯进行羰基化环化反应中也表现高效，以良好产率得到了理想的2-取代的4H-3,1-苯并噁嗪-4-酮（4）。此外，这种Pd-NHC配合物在对碘苯衍生物进行羟基羰基化反应中也证明是一种非常高效的催化剂，催化剂用量低且在低CO压力下。这些结果展示了这种不含膦的Pd(II)-NHC配合物在温和条件下对芳基碘化物进行不同类型羰基化反应的多功能性和高效性。
• Divergent synthesis of flavones and aurones via base-controlled regioselective palladium catalyzed carbonylative cyclization
  作者：Shan Xu、Huaming Sun、Mengyuan Zhuang、Shaohua Zheng、Yajun Jian、Weiqiang Zhang、Ziwei Gao

  DOI：10.1016/j.mcat.2018.03.021

  日期：2018.6

  A regioselective approach for construction of 5-membered and 6-membered flavonoid is established by Pd catalyzed carbonylative cyclization of 2-iodophenol with terminal alkynes using different amine bases under mild reaction condition. The catalytic experiments found that piperazine preferentially accelerate 6-endo cyclization, and triethylamine mediated Pd catalyzed 5-exo cyclization. Under optimized

  在温和的反应条件下，使用不同的胺碱，通过钯催化的2-碘苯酚与末端炔烃的羰基化环化反应，建立了一种构建5元和6元类黄酮的区域选择性方法。催化实验发现，哌嗪优先促进6-内环化，三乙胺介导的Pd催化5-外环化。在优化的反应条件下，Pd催化的羰基化方案成功地以优异的收率和区域选择性应用于39个实例的各种结构。
• Synthesis of chiral chromanols <i>via</i> a RuPHOX–Ru catalyzed asymmetric hydrogenation of chromones
  作者：Yujie Ma、Jing Li、Jianxun Ye、Delong Liu、Wanbin Zhang

  DOI：10.1039/c8cc07787h

  日期：——

  Chiral chromanols and their derivatives have been synthesized via a RuPHOX–Ru catalyzed asymmetric hydrogenation of chromones in high yields, >20 : 1 drs and with up to 99.9% ee. Control experiments show that the reaction undergoes two sequential asymmetric hydrogenation steps of the CC and CO double bonds. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to

  通过RuPHOX-Ru催化色酮的不对称氢化，以高产率，> 20：1 drs和最高99.9％ee合成了手性苯甲酚及其衍生物。对照实验表明，该反应经历了C C和C O双键的两个连续的不对称氢化步骤。该反应可以以克级进行，具有相对较低的催化剂负载量（最高1000 S / C），并且所得产物可以转化为几种生物活性化合物。