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2-(naphthalen-1-ylmethylene)benzofuran-3(2H)-one

中文名称
——
中文别名
——
英文名称
2-(naphthalen-1-ylmethylene)benzofuran-3(2H)-one
英文别名
2-(naphthalen-1-ylmethylidene)-1-benzofuran-3-one
2-(naphthalen-1-ylmethylene)benzofuran-3(2H)-one化学式
CAS
——
化学式
C19H12O2
mdl
——
分子量
272.303
InChiKey
YVPRZKWGPAJIKN-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.46
  • 重原子数:
    21.0
  • 可旋转键数:
    1.0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    26.3
  • 氢给体数:
    0.0
  • 氢受体数:
    2.0

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-(naphthalen-1-ylmethylene)benzofuran-3(2H)-one四甲基乙二胺二氢吡啶sodium hexamethyldisilazane四氯化钛 作用下, 以 四氢呋喃二氯甲烷 为溶剂, 反应 3.75h, 生成 allyl (2-(naphthalen-1-ylmethyl)benzofuran-3-yl) carbonate
    参考文献:
    名称:
    钯催化脱羧脱芳基不对称烯丙基烷基化的光学活性黄酮类分子
    摘要:
    借助一类新发现的带有手性环烷烃骨架的 Trost 型双膦配体,Pd 催化的苯并呋喃脱羧脱芳基不对称烯丙基烷基化 (AAA) 高效 [0.2-1.0 mol% Pd2(dba)3 /L],良好的通用性和高对映选择性(> 30 个实例,82-99% 产率和 90-96% ee)。此外,公开了以前无法到达的黄酮类化合物的面向多样性的合成(DOS)。它具有可靠且可扩展的新开发的 Tsuji-Trost-Stoltz AAA 序列、Wacker-Grubbs-Stoltz 氧化、安息香内缩合和共轭加成,可有效构建具有挑战性的紧凑型具有连续立体中心的环戊二烯[b]苯并呋喃支架。该策略为开发基于黄格兰的药物提供了新途径。
    DOI:
    10.1021/jacs.0c05113
  • 作为产物:
    描述:
    1-(2-hydroxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one吡啶mercury(II) diacetate 作用下, 反应 1.0h, 以65%的产率得到2-(naphthalen-1-ylmethylene)benzofuran-3(2H)-one
    参考文献:
    名称:
    Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives
    摘要:
    A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1-20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1-5, 7-17, 19) were found to be selective towards hMAO-B, while two were non -selective (6 and 20) and one (18) selective towards hMAO-A. Compound 17 (Ki = 0.10 +/- 0.01 mu mol/L) was found to be equally potent and selective towards hMAO-B, when compared with the standard drug Selegiline (Ki = 0.12 0.01 p.mol/L). Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences hMAO-B inhibitory potency, while their structural bulkiness influences selectivity between hMAO-A and hMAO-B. Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
    DOI:
    10.1016/j.cclet.2017.02.009
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文献信息

  • Bifunctional N-Heterocyclic Carbene Catalyzed [3+4] Annulation of Enals and Aurones
    作者:Zhi-Qin Liang、Zhong-Hua Gao、Wen-Qiang Jia、Song Ye
    DOI:10.1002/chem.201405828
    日期:2015.1.26
    Bifunctional N‐heterocyclic carbenes with a free hydroxy group are demonstrated as efficient catalysts for the [3+4] annulation of enals with aurones to give the corresponding benzofuran‐fused ε‐lactones in good yields with good diastereoselectivities and excellent enantioselectivities. Control experiments reveal that the [3+4] cycloadducts are kinetically favored and could be transformed to the thermodynamically
    具有游离羟基的双官能N-杂环卡宾被证明是有效的催化剂,用于环戊烷的[3 + 4]环环氧化,以高收率,良好的非对映选择性和出色的对映选择性提供相应的苯并呋喃稠合的ε-内酯。对照实验表明,[3 + 4]环加合物具有动力学上的优势,可以通过非双功能NHC催化剂转化为热力学上有利的[3 + 2]环加合物。
  • 一种氢氧化钠催化的多取代吡咯合成新方法
    申请人:重庆大学
    公开号:CN110683979B
    公开(公告)日:2022-09-09
    吡咯是一类重要的含氮五元杂环化合物,广泛存在于天然产物,药物以及功能材料中,同时也是重要的合成中间体。本发明涉及多取代吡咯衍生物的催化合成方法,是以异氰基乙酸酯类化合物与橙酮衍生物在氢氧化钠催化下进行1,3‑偶极环加成反应,然后通过开环异构得到对应产物。该反应能够快速、高效地构建多取代吡咯衍生物,具有很高的原子经济性。本发明所用底物易于制备、价格低廉,反应条件温和,操作简单,且底物适用范围广,不需要进行无水无氧操作,即可高收率得到目标化合物,具有广阔的应用前景。
  • Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5 + 4) Cycloadditions
    作者:Anaïs Scuiller、Alexandre Karnat、Nicolas Casaretto、Alexis Archambeau
    DOI:10.1021/acs.orglett.1c00477
    日期:2021.3.19
    Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity and behaved as an all-carbon 1,5-dipole. A N,N-bidentate ligand was required to inhibit the formation of thermodynamic (3 + 2) cycloadducts.
    通过在活化的乙烯基环丙烷和1-氮杂二烯之间进行钯催化的(5 + 4)环加成反应来制备氮杂酮。在此过程中,乙烯基环丙烷伙伴表现出不同寻常的反应性,表现为全碳1,5-偶极子。需要N,N双齿配体来抑制热力学(3 + 2)环加合物的形成。
  • Palladium-Catalyzed Diastereo- and Enantioselective [3 + 2] Cycloaddition of Vinylcyclopropanes with Azadienes: Efficient Access to Chiral Spirocycles
    作者:Kai Liu、Jianfeng Yang、Xiaoxun Li
    DOI:10.1021/acs.orglett.0c04062
    日期:2021.2.5
    azadienes (BDAs) have been widely used as four-atom synthons in transition-metal-mediated cycloaddition reactions, while the exploitation of their reactivity as a two-atom unit to construct spirocycles is still underdeveloped. Herein, we reported the first palladium(0)-catalyzed diastereo- and enantioselective [3 + 2] annulation of vinylcyclopropanes (VCPs) and BDAs. This transformation is featured with
    苯并呋喃衍生的氮杂二烯(BDA)已广泛用作过渡金属介导的环加成反应中的四原子合成子,而利用其作为二原子单元构建螺环的反应性仍然不发达。在这里,我们报道了乙烯基环丙烷(VCP)和BDA的第一个钯(0)催化的非对映和对映选择性[3 + 2]环化反应。该转化具有广泛的底物范围(31个实例),可轻松获得具有季立体位中心的多种对映体富集的螺环,产率高,具有良好的区域,非对映和对映选择性(高达93%的产率,>在温和的反应条件下为20:1 dr,并且大多数> 99%ee)。而且,螺环产物可以有效地转化为结构复杂的三环[8.3.0.01,5 ]-氮杂十七烷和三环[7.3.0.0 1,5 ]-氮杂十二烷骨架。
  • Regio- and Diastereoselective Spirocyclopropanation of Benzofuran-Derived Azadienes through 1,4-Addition-Induced Dearomatization Reaction under Mild Conditions
    作者:Qing-Yun Fang、Meng-Hao Yi、Xiao-Xia Wu、Li-Ming Zhao
    DOI:10.1021/acs.orglett.0c01987
    日期:2020.7.2
    A Cs2CO3-mediated [2 + 1] cycloaddition of benzofuran-derived azadienes (BDAs) with bromomalonate by using a dearomatization strategy has been developed. Through this process, BDAs serve as a potential 2-atom synthon in the construction of a range of functionalized spirocyclopropane derivatives, such as spirobenzofuran-2-cyclopropanes and spiroindane-2-cyclopropanes.
    通过使用脱芳香化策略,已开发出Cs 2 CO 3介导的苯并呋喃衍生的氮杂二烯(BDA)与溴丙二酸酯的[2 +1]环加成反应。通过此过程,BDA在构建一系列功能化的螺环丙烷衍生物(如螺苯并呋喃-2-环丙烷和螺茚满-2-环丙烷)中充当潜在的2原子合成子。
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同类化合物

降钙素 金色草素 苦杏碱醇B 海生菊甙 噢弄斯定 E-2-[(4-甲氧基苯基)亚甲基]苯并[b]呋喃-3-酮 6-羟基-2-[羟基-(4-羟基苯基)甲基]-1-苯并呋喃-3-酮 6,4''-二羟基橙酮 5-乙酰基-2-苯甲酰基-1-苯并呋喃-3-酮 3(2H)-苯并呋喃酮,4,6-二羟基-2-[(4-羟基苯基)亚甲基]-,(2Z)- 3',5'-二溴-2',4,4',6-四羟基橙酮 2-苯甲酰基-6-甲氧基-1-苯并呋喃-3-酮 2-苯甲酰基-5-甲基-1-苯并呋喃-3-酮 2-苯甲酰基-1-苯并呋喃-3(2H)-酮 2-苯甲酰-2-羟基-1-苯并呋喃-3-酮 2-氨基-6-氯-3-硝基吡啶 2-氨基-2-苄基-1-苯并呋喃-3-酮 2-[(Z)-(3,4-二羟基苯基)亚甲基]-6-羟基-7-甲氧基苯并呋喃-3(2H)-酮 2-[(4-羟基-3-甲氧基苯基)亚甲基]-7-甲氧基-1-苯并呋喃-3-酮 2-[(4-硝基苯基)亚甲基]-1-苯并呋喃-3-酮 2-[(4-甲氧基苯基)亚甲基]-5-甲基-1-苯并呋喃-3-酮 2-[(4-溴苯基)亚甲基]-1-苯并呋喃-3-酮 2-[(4-氟苯基)亚甲基]-6-羟基-1-苯并呋喃-3-酮 2-[(4-氟苯基)亚甲基]-6-甲氧基-1-苯并呋喃-3-酮 2-[(4-氟苯基)亚甲基]-5-甲基-1-苯并呋喃-3-酮 2-[(3-甲氧基苯基)亚甲基]-1-苯并呋喃-3-酮 2-[(3-甲基苯基)亚甲基]-1-苯并呋喃-3-酮 2-[(3,4-二甲氧基苯基)亚甲基]-1-苯并呋喃-3-酮 2-(4-甲氧基苯甲酰基)-1-苯并呋喃-3-酮 2-(3,4-二羟基苯甲酰)-2,4,6-三羟基-1-苯并呋喃-3-酮 2-(3,4-二羟基苯亚甲基)-6-羟基-3(2H)-苯并呋喃酮 2-(3,4-二羟基亚苄基)苯并呋喃-3(2H)-酮 1H-萘并[2,1-b]吡喃-2-甲腈,3-氨基-1-(2-氟苯基)- 1,1-二甲基铟烷-5,6-二醇 1,1,2-三甲基肼二盐酸 (Z)-4,6-二羟基橙酮 (7Z)-4-羟基-7-(苯基甲亚基)呋喃并[3,2-e][1,3]苯并二噁唑-8(7H)-酮 (2Z)-4,6-二羟基-2-[(3,4,5-三羟基苯基)亚甲基]-1-苯并呋喃-3-酮 (2E)-2-[(3-硝基苯基)亚甲基]-1-苯并呋喃-3-酮 2-((Z)-2,4-dimethoxy-benzylidene)-5-methyl-benzofuran-3-one (2Z)-5-[(dimethylamino)methyl]-6-hydroxy-2-(4-methoxybenzylidene)-7-methyl-1-benzofuran-3(2H)-one (2Z)-2-(2,4-dimethoxybenzylidene)-6-hydroxy-7-{[(2S)-2-(pyridin-3-yl)piperidin-1-yl]methyl}-1-benzofuran-3(2H)-one (2Z)-2-(3,4-dimethoxybenzylidene)-5-[(dimethylamino)-methyl]-6-hydroxy-7-methyl-1-benzofuran-3(2H)-one (Z)-2-(2,4-dimethoxybenzylidene)-6-hydroxybenzofuran-3(2H)-one (2Z)-6-hydroxy-2-(4-methoxybenzylidene)-7-{[(2S)-2-(pyridin-3-yl)piperidin-1-yl]methyl}-1-benzofuran-3(2H)-one (2Z)-6-hydroxy-7-{[(2S)-2-(pyridin-3-yl)piperidin-1-yl]-methyl}-2-(3,4,5-trimethoxybenzylidene)-1-benzofuran-3(2H)-one (2Z)-6-hydroxy-7-{[(2S)-2-(pyridin-3-yl)piperidin-1-yl]-methyl}-2-(2,3,4-trimethoxybenzylidene)-1-benzofuran-3(2H)-one (2Z)-2-(2,3-dimethoxybenzylidene)-6-hydroxy-7-{[(2S)-2-(pyridin-3-yl)piperidin-1-yl]methyl}-1-benzofuran-3(2H)-one (Z)-2-(2-hydroxy-3-methoxybenzylidene)benzofuran-3(2H)-one (Z)-2-(4-bromobenzylidene)-6-hydroxy-7-methylbenzofuran-3(2H)-one