4-(4-oxochroman-2-yl)benzaldehyde

• 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: 4-(4-oxochroman-2-yl)benzaldehyde
• 英文别名: 4-(4-Oxo-2,3-dihydrochromen-2-yl)benzaldehyde；4-(4-oxo-2,3-dihydrochromen-2-yl)benzaldehyde
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: HOZFCXLRHMSGGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  4-(4-oxochroman-2-yl)benzaldehyde 、 对甲苯磺酸 、 (S)-1-(4-bromophenyl)but-3-en-1-ol 以 氯仿 、 水 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Synthesis of flavonoids based novel tetrahydropyran conjugates (Prins products) and their antiproliferative activity against human cancer cell lines

  摘要：

  Following our previously reported Prins cyclization strategy, a series of novel and highly functionalized flavonoid based THPs (Prins products) were designed, synthesized and evaluated for their anti-proliferative activity. Novel products were afforded in excellent yields (72-96%) within 20-90 min at 62 degrees C using flavonoid aldehydes, homoallylic alcohols, p-TSA center dot H2O (catalyst and reagent) and MS 4 angstrom in CHCl3. Deprotection of tosyl group was achieved with TFA (catalyst and solvent) at 140 degrees C to obtain 4-hydroxytetrahydropyrans and further reaction of 4-hydroxytetrahydropyrans with cinnamoyl chloride afforded 4-cinnamate tetrahydropyrans under neat condition. Synthesized compounds evaluated against human cancer cell lines (Hep3 beta, MCF-7 and Hela), have shown moderate to good antiproliferative activity in vivo. Compounds 3q and 3zb exhibited similar cytotoxicity (IC50 6.6 +/- 1.4, 6.9 +/- 1.0 mu M, respectively) to the reference drug doxorubicin (IC50 7.6 +/- 0.9 mu M) against the MCF-7 cancer cell line. Compound 3zb was found equally active as the standard drug (IC50 4.48 +/- 2.1 mu M) against the Hep3 beta cell line and compounds 3c and 3q showed moderate cytotoxicity (IC50 10.40 +/- 1.1, 12.9 +/- 1.7 mu M, respectively) against the HeLa cell line. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.033
• 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 4-(4-oxochroman-2-yl)benzaldehyde
  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

• 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。
• Direct α-Arylation/Heteroarylation of 2-Trifluoroboratochromanones via Photoredox/Nickel Dual Catalysis
  作者：Jennifer K. Matsui、Gary A. Molander

  DOI：10.1021/acs.orglett.6b03448

  日期：2017.2.3

  Utilizing photoredox/nickel dual catalysis, diverse flavanones have been synthesized by coupling novel 2-trifluoroboratochromanone building blocks with aryl and heteroaryl bromide partners. The newly reported trifluoroborato-chromanones can be easily accessed from the corresponding chromones on multigram scale. This represents a general route for accessing natural and unnatural flavanones that were previously formed through a synthetically more restrictive ring closure route from chalcone precursors.
• Synthesis of flavonoids based novel tetrahydropyran conjugates (Prins products) and their antiproliferative activity against human cancer cell lines
  作者：Naseem Ahmed、Naveen Kumar Konduru、Sarfaraz Ahmad、Mohammad Owais

  DOI：10.1016/j.ejmech.2014.01.033

  日期：2014.3

  Following our previously reported Prins cyclization strategy, a series of novel and highly functionalized flavonoid based THPs (Prins products) were designed, synthesized and evaluated for their anti-proliferative activity. Novel products were afforded in excellent yields (72-96%) within 20-90 min at 62 degrees C using flavonoid aldehydes, homoallylic alcohols, p-TSA center dot H2O (catalyst and reagent) and MS 4 angstrom in CHCl3. Deprotection of tosyl group was achieved with TFA (catalyst and solvent) at 140 degrees C to obtain 4-hydroxytetrahydropyrans and further reaction of 4-hydroxytetrahydropyrans with cinnamoyl chloride afforded 4-cinnamate tetrahydropyrans under neat condition. Synthesized compounds evaluated against human cancer cell lines (Hep3 beta, MCF-7 and Hela), have shown moderate to good antiproliferative activity in vivo. Compounds 3q and 3zb exhibited similar cytotoxicity (IC50 6.6 +/- 1.4, 6.9 +/- 1.0 mu M, respectively) to the reference drug doxorubicin (IC50 7.6 +/- 0.9 mu M) against the MCF-7 cancer cell line. Compound 3zb was found equally active as the standard drug (IC50 4.48 +/- 2.1 mu M) against the Hep3 beta cell line and compounds 3c and 3q showed moderate cytotoxicity (IC50 10.40 +/- 1.1, 12.9 +/- 1.7 mu M, respectively) against the HeLa cell line. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids
  作者：Hyung-Seok Yoo、Seung Hwan Son、Yang Yil Cho、Soo Jin Lee、Hyu Jeong Jang、Young Min Kim、Dong Hwan Kim、Nam Yong Kim、Boyoung Y. Park、Yong Sup Lee、Nam-Jung Kim

  DOI：10.1021/acs.joc.9b01162

  日期：2019.8.16

  total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92%.

  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。