2-(4-(tert-butyl)phenyl)chroman-4-one | 77038-30-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-(tert-butyl)phenyl)chroman-4-one
• 英文别名: 2-(4-Tert-butylphenyl)-2,3-dihydrochromen-4-one
• CAS: 77038-30-3
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: OTTAJXQZWRXAEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  四甲基甲烷二胺 、 2-(4-(tert-butyl)phenyl)chroman-4-one 在 乙酸酐 作用下， 反应 1.0h， 以6%的产率得到4'-t-butyl-3-methylene flavanone
  参考文献：
  名称：

  Antimicrobial 3-methylene flavanones

  摘要：

  The antimicrobial activity previously attributed to flavanone Mannich bases was found to be due to their breakdown products, 3-methyleneflavanones. Among the latter compounds, highest potency was observed when the flavanone phenyl ring contained bromine or chlorine substituents. 3-Methylene-2-phenylflavanone (8) was synthesized and shown to be equal to hexachlorophene in tests against representative Gram-positive microorganisms.

  DOI：

  10.1021/jm00141a011
• 作为产物：
  描述：

  3-苯氧基丙腈 在 2,2'-联吡啶 、 palladium(II) trifluoroacetate 、 三氟甲磺酸 、 氧气 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 2-(4-(tert-butyl)phenyl)chroman-4-one
  参考文献：
  名称：

  通过钯（II）催化色胺酮与芳基硼酸的一锅β-芳基化反应合成黄酮。

  摘要：

  合宜地通过一锅二价的苯并二氢吡喃酮与芳基硼酸通过串联钯（II）催化合成了苯并二氢吡喃酮（一类具有化学未活化β位点的简单酮），合成了47种黄烷酮。该反应提供了一种以高达92％的收率获得各种黄烷酮（包括天然产物，如柚皮苷三甲醚）的新颖途径。

  DOI：

  10.1021/acs.joc.9b01162

文献信息

• 3-Methylene flavanones and 3-methylene chromanones
  申请人：Miles Laboratories, Inc.

  公开号：US04241069A1

  公开（公告）日：1980-12-23

  Compounds which are 3-methylene flavanones and 3-methylene chromanones having activity against microorganisms are disclosed. The compounds are represented by the general structural formula: ##STR1## wherein: R.sup.1 is a member selected from the group consisting of hydrogen, Br, CH.sub.3 and OCH.sub.3 ; R.sup.2 is selected from the group consisting of hydrogen and ##STR2## wherein R.sup.4 is a member selected from the group consisting of hydrogen, Br, Cl, CH.sub.3, OCH.sub.3, NO.sub.2, N(CH.sub.3).sub.3 and CN; R.sup.5 is selected from the group consisting of hydrogen and Cl, with the proviso that when R.sup.5 is Cl, R.sup.4 is hydrogen or Cl; and R.sup.3 is selected from the group consisting of hydrogen, phenyl, 2-thienyl, 4-pyridyl and naphthyl, with the proviso that when R.sup.3 is naphthyl, R.sup.1 and R.sup.2 are hydrogen.

  揭示了对微生物具有活性的3-亚甲基黄酮和3-亚甲基色酮类化合物。这些化合物由以下一般结构式表示：其中：R.sup.1是从氢、Br、CH.sub.3和OCH.sub.3组成的群体中选取的成员；R.sup.2是从氢和##STR2##组成的群体中选取的成员，其中R.sup.4是从氢、Br、Cl、CH.sub.3、OCH.sub.3、NO.sub.2、N(CH.sub.3).sub.3和CN组成的群体中选取的成员；R.sup.5是从氢和Cl组成的群体中选取的成员，但有一个条件是当R.sup.5是Cl时，R.sup.4是氢或Cl；R.sup.3是从氢、苯基、2-噻吩基、4-吡啶基和萘基组成的群体中选取的成员，但有一个条件是当R.sup.3是萘基时，R.sup.1和R.sup.2是氢。
• Palladium-Catalyzed [3+3] Annulation of Vinyl Chromium(0) Carbene Complexes through Carbene Migratory Insertion/Tsuji-Trost Reaction
  作者：Kang Wang、Yifan Ping、Taiwei Chang、Jianbo Wang

  DOI：10.1002/anie.201707590

  日期：2017.10.9

  Vinyl chromium(0) Fischer carbene complexes were employed as the source of π‐allylic palladium species for catalytic [3+3] annulation under palladium catalysis. Mechanistically, this transformation is proposed to involve carbene migratory insertion and intramolecular Tsuji–Trost reaction as the key steps. Substituted six‐membered heterocyclic flavonones and quinolines are obtained, depending on the

  乙烯基铬（0）菲舍尔卡宾络合物被用作π烯丙基钯物质的来源，用于钯催化下的催化[3 + 3]环化。从机理上讲，这种转化被认为包括卡宾迁移插入和分子内Tsuji-Trost反应作为关键步骤。根据偶联伙伴上的亲核官能团，获得了取代的六元杂环黄酮和喹啉。
• Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Chromones: A Highly Enantioselective Pathway for Accessing Chiral Flavanones
  作者：Qijie He、Chau Ming So、Zhaoxiang Bian、Tamio Hayashi、Jun Wang

  DOI：10.1002/asia.201403290

  日期：2015.3

  Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4‐addition of α,β‐unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)‐Ph‐bod*, the 1,4‐addition of a variety of arylboronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97 % ee, 99 % ee for

  在不对称的α，β-不饱和羰基化合物的1,4加成反应中，苯醌是最具挑战性的底物之一。通过使用与手性二烯配体（R，R）-Ph-bod *缔合的铑配合物，实现了各种芳基硼酸的1,4加成，从而获得了高产率的相应黄烷酮，具有出色的对映选择性（≥ ee为97％ee，大多数基材为99％ee）。在规定的反应条件下，未观察到会导致产物对映选择性下降的开环副产物。
• Synthetic approach to flavanones and flavones via ligand-free palladium(ii)-catalyzed conjugate addition of arylboronic acids to chromones
  作者：Donghee Kim、Kyungrok Ham、Sungwoo Hong

  DOI：10.1039/c2ob26061a

  日期：——

  The remarkable catalytic effects of Fe(OTf)3 in the context of the Pd(II)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO2 to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds.

  在Pd(II)催化的芳基硼酸与色酮的共轭加成反应中，Fe(OTf)3显示出了显著的催化效应，能够在温和条件下合成各种黄酮。向反应中添加催化量的DDQ和KNO2则专门产生黄酮类似物。该转化的反应范围相当广泛，提供了良好的收率，合成了多种黄酮和黄酮类化合物，这些化合物在许多生物活性化合物中是具优势的结构。
• Synthesis, Crystal Structure and Antitumour Activity Evaluation of 1<i>H</i>-thieno[2,3-<i>c</i>]chromen-4(2<i>H</i>)-one Derivatives
  作者：Huchang Yu、Yan Li、Zhiyuan Feng、Hongwu Jiang、Yinglan Zhao、Youfu Luo、Wencai Huang、Zicheng Li

  DOI：10.3184/174751917x14837116219573

  日期：2017.1

  diffraction analysis. A preliminary antitumour screening showed that 2-(2-fluorophenyl)-1H-thieno [2,3-c]chromen-4(2H)-one had moderate to good activity against A549, BGC-823, HCT116 and MDA-MB-453 cancer cell lines, and 2-(3,4-dimethoxyphenyl)-1H-thieno[2,3-c]chromen-4(2H)-one displayed similar activity against these four kinds of cancer cells compared with the reference drug.

  在哌啶的存在下，通过取代的黄烷酮与噻唑烷-2,4-二酮在乙醇中的 Knoevenagel 缩合，合成了一系列 1H-噻吩并 [2,3-c]chromen-4(2H)-one 衍生物。提出了反应机理。所有合成的化合物均通过 IR、1H NMR、13C NMR、HRMS 和元素分析进行​​表征。2-(3-氯苯基)-1H-thieno[2,3-c]chromen-4(2H)-one 的结构通过单晶 X 射线衍射分析得到证实。初步的抗肿瘤筛选表明 2-(2-fluorophenyl)-1H-thieno [2,3-c]chromen-4(2H)-one 对 A549、BGC-823、HCT116 和 MDA-MB-具有中等至良好的活性与参考药物相比，453 种癌细胞系和 2-(3,4-二甲氧基苯基)-1H-噻吩并[2,3-c]色烯-4(2H)-one 对这四种癌细胞表现出相似的活性。