1-(1-Benzofuran-2-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one | 107155-10-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(1-Benzofuran-2-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 107155-10-2
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: DEGGMFLARURDBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  1-(1-Benzofuran-2-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以74%的产率得到3-(benzofuran-2-yl)-5-(2-hydroxyphenyl)-2-pyrazoline
  参考文献：
  名称：

  3-(Substituted Aryl)-1-benzofuranyl-2-propenones: Antimicrobial Properties of Some Chalcones-Type Compounds and their 2-Pyrazoline Derivatives

  摘要：

  在甲醇性氢氧化钾溶液中，2-乙酰基苯并呋喃与呋喃-2-甲醛和吡咯-2-甲醛缩合，生成相应的苯并呋喃香豆素。这两种化合物和之前合成的九种苯并呋喃香豆素进一步与乙醇中的水合肼反应，形成2-吡唑啉衍生物。所有合成的化合物均通过元素分析、熔点测定、红外光谱和核磁共振光谱进行表征。对九种香豆素类化合物和十一种2-吡唑啉进行了对六种细菌和三种酵母的生物活性评估，发现十三种化合物表现出活性，其中四种是香豆素类化合物表现出不同程度的活性。

  DOI：

  10.1155/2011/806854
• 作为产物：
  描述：

  2-乙酰基苯并呋喃 、 水杨醛 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 130.0 ℃ 、1.0 MPa 条件下， 反应 0.17h， 生成 1-(1-Benzofuran-2-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs

  摘要：

  Twenty-eight newer 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs were synthesized by microwave irradiation method and evaluated for in-vitro and in-vivo antitubercular activity against multidrug-resistant M. tuberculosis stains. Structure activity relationship study was carried out and found NO2 (o) substituted 3-benzo-furan-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin was most potent antitubercular agent against M. tuberculosis, even better than standard drug isoniazid and comparable with rifampin. Other synthesized compounds 7j, 7f, 7a, 7e and 5d, 5f were found moderate to good activity in in-vitro model at lower IC50 values 85 mu M, 154 mu M, 157 mu M, 164 mu M, 170 mu M and 190 mu ML respectively. In in-vivo animal model compound 7j was drastically reduced the bacterial load in lung and spleen tissues at the dose of 25 mg/kg body weight. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.035

文献信息

• Enantioselective Formal [4 + 2] Annulation of <i>ortho</i>-Quinone Methides with <i>ortho</i>-Hydroxyphenyl α,β-Unsaturated Compounds
  作者：Jianlin Zhang、Xiaohua Liu、Songsong Guo、Changqiang He、Wanlong Xiao、Lili Lin、Xiaoming Feng

  DOI：10.1021/acs.joc.8b01425

  日期：2018.9.7

  The highly efficient enantioselective [4 + 2] cycloaddition of o-QMs with ortho-hydroxyphenyl-substituted α,β-unsaturated compounds was realized by using a chiral N,N′-dioxide-Sc(III) complex as catalyst. A variety of chiral chromane derivatives with three continuous stereocenters were obtained in excellent results (up to 99% yield, >19:1 dr, and 99% ee) under as low as 0.005–1 mol % catalyst loading

  以手性N，N′-二氧化物-Sc（III）配合物为催化剂，可实现邻-羟基苯基取代的α，β-不饱和化合物对o - QMs的高效对映选择性[4 + 2]环加成反应。在低至0.005–1 mol％的催化剂负载量下，获得了具有三个连续立体中心的各种手性苯并二氢吡喃衍生物，具有优异的结果（产率高达99％，dr> 19：1和ee达到99％）。此外，提出了具有可能的过渡态模型的催化循环，以阐明手性的起源。
• Organocatalytic Asymmetric Cascade Reaction of 2-Hydroxyphenyl-Substituted Enones and Isocyanates To Construct 1,3-Benzoxazin-2-ones
  作者：Songsong Guo、Xiaohua Liu、Bin Shen、Lili Lin、Xiaoming Feng

  DOI：10.1021/acs.orglett.6b02522

  日期：2016.10.7

  a new bisguanidinium salt as a multifunctional organocatalyst for asymmetric cascade esterification/aza-Michael reaction between 2-hydroxyphenyl-substituted enones and isocyanates is reported. A high level of enantioinduction and excellent isolated yields were achieved under mild reaction conditions. Enantiomerically enriched 1,3-benzoxazin-2-ones were constructed, and a possible catalytic model was

  据报道，开发了一种新的双胍盐作为多功能有机催化剂，用于2-羟基苯基取代的烯酮和异氰酸酯之间的不对称级联酯化/氮杂-迈克尔反应。在温和的反应条件下，实现了高水平的对映体诱导和出色的分离产率。构建了对映体富集的1,3-苯并恶嗪-2-酮，并基于机理驱动的实验，提出了可能的催化模型。
• Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs
  作者：Kuntal Manna、Yadvendra K. Agrawal

  DOI：10.1016/j.ejmech.2010.05.035

  日期：2010.9

  Twenty-eight newer 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs were synthesized by microwave irradiation method and evaluated for in-vitro and in-vivo antitubercular activity against multidrug-resistant M. tuberculosis stains. Structure activity relationship study was carried out and found NO2 (o) substituted 3-benzo-furan-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin was most potent antitubercular agent against M. tuberculosis, even better than standard drug isoniazid and comparable with rifampin. Other synthesized compounds 7j, 7f, 7a, 7e and 5d, 5f were found moderate to good activity in in-vitro model at lower IC50 values 85 mu M, 154 mu M, 157 mu M, 164 mu M, 170 mu M and 190 mu ML respectively. In in-vivo animal model compound 7j was drastically reduced the bacterial load in lung and spleen tissues at the dose of 25 mg/kg body weight. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 3-(Substituted Aryl)-1-benzofuranyl-2-propenones: Antimicrobial Properties of Some Chalcones-Type Compounds and their 2-Pyrazoline Derivatives
  作者：Demet Coskun、Misir Ahmedzade、Sevda Kirbag

  DOI：10.1155/2011/806854

  日期：——

  2-Acetylbenzofuran on condensation with furan-2-carboxaldehyde and pyrrole-2-carboxaldehyde in methanolic KOH solution yielded the corresponding benzofuran chalcones. These two compounds and nine benzofuran chalcones were synthesized before, were further reacted with hydrazine hydrate in ethanol which led to the formation of 2-pyrazoline derivatives. All the synthesized compounds were characterized by elemental analysis, melting point determination, infrared spectroscopy and nuclear magnetic resonance spectroscopy. Nine chalcone-type compounds and eleven 2-pyrazolines were evaluated for their biological activities against the six bacteria and the three yeast and it was seen that thirteen compounds showed activity. Four of them are chalcone-type compounds showed more or less activity.

  在甲醇性氢氧化钾溶液中，2-乙酰基苯并呋喃与呋喃-2-甲醛和吡咯-2-甲醛缩合，生成相应的苯并呋喃香豆素。这两种化合物和之前合成的九种苯并呋喃香豆素进一步与乙醇中的水合肼反应，形成2-吡唑啉衍生物。所有合成的化合物均通过元素分析、熔点测定、红外光谱和核磁共振光谱进行表征。对九种香豆素类化合物和十一种2-吡唑啉进行了对六种细菌和三种酵母的生物活性评估，发现十三种化合物表现出活性，其中四种是香豆素类化合物表现出不同程度的活性。