2-hexyl-4H-chromen-4-one | 158634-34-5

• 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-hexyl-4H-chromen-4-one
• 英文别名: 2-Hexylchromen-4-one
• CAS: 158634-34-5
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: YEDXHKMXARLJRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-hexyl-4H-chromen-4-one 在 palladium on activated charcoal 盐酸 、 氢气 、 溴 作用下， 以 乙醇 为溶剂， 反应 60.0h， 生成 6-Bromo-2-hexyl-2,3-dihydrobenzopyran
  参考文献：
  名称：

  Synthesis and Properties of a New Family of Chiral Mesogens Containing the 2,3-Dihydrobenzopyran Nucleus

  摘要：

  A new class of mesogens A with a central chiral core based on the 2,3-dihydrobenzopyran nucleus was synthesized both in the racemic and optically pure form, and the thermotropic properties were studied. The distortion from structural linearity due to the presence of the 2,3-dihydropyran ring does not inhibit the existence of mesophases, and Ch, S-A, and S-C phases were observed according to the substituents present. The conformational constrictions imposed by cyclization proved not to be very important in determining the compactness of the cholesteric helix.

  DOI：

  10.1021/jo00099a022
• 作为产物：
  描述：

  1-(2-acetoxyphenyl)-2-nonyn-1-one 在 哌嗪 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以93%的产率得到2-hexyl-4H-chromen-4-one
  参考文献：
  名称：

  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

  摘要：

  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。

  公开号：

  CN105175375B

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。
• Synthesis of Chromones via Palladium-Catalyzed Ligand-Free Cyclocarbonylation of <i>o</i>-Iodophenols with Terminal Acetylenes in Phosphonium Salt Ionic Liquids
  作者：Qian Yang、Howard Alper

  DOI：10.1021/jo902210p

  日期：2010.2.5

  The highly efficient and selective palladium-catalyzed ligand-free cyclocarbonylation reaction of o-iodophenols with terminal acetylenes and CO in the phosphonium salt ionic liquid, C14H29(C6H13)3P+Br−, affords diversified chromones in good to excellent yields under atmospheric CO pressure. The ionic liquid, as the reaction medium, enhances the efficiency of the cyclocarbonylation reaction.

  高效和选择性的钯催化的无配体的cyclocarbonylation的反应Ó在鏻盐离子性液体终端乙炔和CO -iodophenols，C 14 H ^ 29（C 6 H ^ 13）3 P +溴- ，得到多样化良好色酮类在常压CO压力下具有出色的产量。作为反应介质的离子液体提高了环羰基化反应的效率。
• Synthesis of 4<i>H</i>-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes
  作者：Yixia Yue、Jinsong Peng、Deqiang Wang、Yunyun Bian、Peng Sun、Chunxia Chen

  DOI：10.1021/acs.joc.7b00640

  日期：2017.5.19

  The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh3)4/Xphos as the catalyst and K2CO3 as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane.

  开发了钯催化的烯基溴和醛的分子内酰化反应，以有效合成4 H -chromen-4-ones。以Pd（PPh 3）4 / Xphos为催化剂，以K 2 CO 3为碱，该方案被用于合成少量的，功能多样的黄酮类化合物，在1,4-二恶烷中的产率为中等。
• Synthesis, docking study and relaxant effect of 2-alkyl and 2-naphthylchromones on rat aorta and guinea-pig trachea through phosphodiesterase inhibition
  作者：Fernando Rodríguez-Ramos、Andrés Navarrete、Martín González-Andrade、Carlos Alarcón、Alejandro Aguilera-Cruz、Adelfo Reyes-Ramírez

  DOI：10.1016/j.bioorg.2013.07.001

  日期：2013.10

  heated at reflux temperature, yielding the chromones 11a–11h. Evaluation of the vasorelaxant effect of 4, 11a–11h on rat aorta demonstrated that potency decreases with branched alkyl groups. Whereas the EC50 of compound 11d (substituted by an n-hexyl group) was 8.64 ± 0.39 μM, that of 11f (substituted by an isobutyl group) was 14.58 ± 0.64 μM. Contrarily, the effectiveness of the compound is directly

  色酮（4）构成分离为天然产物的各种类黄酮的基本结构，能够舒缓平滑肌。这与高血压，哮喘和慢性阻塞性肺疾病的治疗有关。前者涉及血管平滑肌（VSM）的收缩，后两者涉及气道平滑肌（ASM）的支气管收缩。类黄酮放松肌肉组织的主要机制之一是抑制VSM和ASM中都存在的磷酸二酯酶（PDE）。因此，一项研究旨在通过抑制PDE来分析色酮衍生物在血管舒张和支气管舒张中的构效关系。对接研究表明，这些色酮在PDE的催化位点结合。所以，我们合成了在C-2位被烷基和萘基取代的色酮的类似物。这些化合物是在DBU和吡啶存在下由2-羟基苯乙酮和酰氯合成的，通过将反应温度从80改变为30°C，并使用二氯甲烷作为溶剂，改变了报道的3-酰基色酮合成的方法。相应的酚酯10a – 10h。这些化合物用等价的DBU，吡啶作为溶剂环化，并在回流温度下加热，得到色酮11a - 11h。的的血管舒张作用的评价4，11A - 11H上大鼠主动