benzofuran-2-yl-(4-tert-butyl-phenyl)-methanone | 14178-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzofuran-2-yl-(4-tert-butyl-phenyl)-methanone
• 英文别名: benzofuran-2-yl(4-(tert-butyl)phenyl)methanone；1-Benzofuran-2-yl-(4-tert-butylphenyl)methanone
• CAS: 14178-69-9
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: RBYQNVCXLMCBLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzofuran-2-yl-(4-tert-butyl-phenyl)-methanone 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 99.0h， 生成 1-[Benzofuran-2-yl-(4-tert-butyl-phenyl)-methyl]-1H-[1,2,4]triazole
  参考文献：
  名称：

  Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles

  摘要：

  Methodology previously described by our group was applied to the preparation of a series of 4-alkyl/aryl-substituted 1-[benzofuran-2-yl-phenylmethyl]-1H-triazoles. The [1,2,4]-triazole derivatives were prepared for a range of alkyl and aryl substituents, and for the 4-methyl, 4-ethyl, 4-'propyl, 4-'butyl, 4-phenyl and 4-chlorophenyl derivatives, the minor [1,3,4]-triazole isomer also isolated. All the triazole derivatives were evaluated for CYP26A1 inhibitory activity using a MCF-7 cell-based assay. The 4-ethyl and 4-phenyl-1,2,4-triazole derivatives displayed inhibitory activity (IC50 4.5 and 7 mu M, respectively) comparable with that of the CYP26 inhibitor liarozole (IC50 7 mu M). Using a CYP26A1 homology model (based on CYP3A4) template, docking experiments were performed with MOE with multiple hydrophobic interactions observed in addition to coordination between the triazole nitrogen and the haem transition metal. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.018
• 作为产物：
  描述：

  (E)-1-(4-tert-Butyl-phenyl)-3-(2-hydroxy-phenyl)-propenone 在 叔丁基过氧化氢 、 sodium azide 、 碘 作用下， 以 乙醇 、 水 为溶剂， 以73%的产率得到benzofuran-2-yl-(4-tert-butyl-phenyl)-methanone
  参考文献：
  名称：

  Intramolecular oxidative coupling: I₂/TBHP/NaN₃-mediated synthesis of benzofuran derivatives

  摘要：

  已建立一种新型分子内氧化偶联反应，用于通过直接C(sp²)–H官能化形成C–O键制备苯并呋喃衍生物。此转化在无金属条件下由I₂/TBHP/NaN₃介导，而催化量的NaN₃在反应中起着关键作用。

  DOI：

  10.1039/c5ob00577a

文献信息

• Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles
  作者：Julin Gong、Kun Hu、Yinlin Shao、Renhao Li、Yetong Zhang、Maolin Hu、Jiuxi Chen

  DOI：10.1039/c9ob02408e

  日期：——

  example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that this tandem process involves sequential nucleophilic addition generating 2

  已经开发了钯催化串联2-（2-酰基苯氧基）乙腈与芳基硼酸的串联/加成反应的第一个实例，为合成具有优异的化学选择性和广泛的官能团相容性的2-芳酰基苯并呋喃提供了新的策略。初步的机理实验表明，该串联过程涉及顺序的亲核加成，产生2-（2-酰基苯氧基）-1-苯基乙-1-酮，然后进行分子内环化。该方法也已用于2-芳酰基吲哚和强效CYP19抑制剂1-（苯并呋喃-2-基（苯基）甲基）-1H-1,2,4-三唑的合成。
• Nickel-Catalyzed Domino Reaction of α-Aryloxyacetonitriles with Arylboronic Acids: Synthesis of 2-Aroylbenzo[<i>b</i>]furans
  作者：Subhashini V. Subramaniam、Vijaya Kumaran Dharmalingam、Anwesha Bhattacharya、Saravanan Peruncheralathan

  DOI：10.1021/acs.orglett.3c03241

  日期：2023.11.24

  We disclose the first catalytic domino reaction of α-(2-formylaryloxy)acetonitriles with arylboronic acids, yielding a range of 2-aroylbenzo[b]furans with yields of up to 93%. Ni(acac)2 serves as an effective dual catalyst. The protocol is also applicable to α-(2-acetylphenoxy)acetonitrile, giving rise to 3-methyl-2-aroylbenzo[b]furans. This domino process is efficient, additive-free, and compatible

  我们公开了 α-(2-甲酰基芳氧基)乙腈与芳基硼酸的首次催化多米诺反应，产生一系列 2-芳酰基苯并[ b ]呋喃，产率高达 93%。Ni(acac) 2是一种有效的双催化剂。该方案也适用于 α-(2-乙酰基苯氧基)乙腈，产生 3-甲基-2-芳酰基苯并[ b ]呋喃。该多米诺骨牌工艺高效、无添加剂，并且与多种芳基硼酸相容，包括带有CF 3、NO 2、CN 和CO 2 Me 基团的芳基硼酸。机理研究强调了镍催化剂促进的双重活化。
• Intramolecular oxidative coupling: I₂/TBHP/NaN₃-mediated synthesis of benzofuran derivatives
  作者：Wengang Xu、Qingcui Li、Chuanpeng Cao、Fanglin Zhang、Hua Zheng

  DOI：10.1039/c5ob00577a

  日期：——

  A novel intramolecular oxidative coupling reaction has been established to prepare benzofuran derivatives via direct C(sp²)–H functionalization for the formation of C–O bonds. This transformation is mediated by I₂/TBHP/NaN₃ under metal-free conditions and a catalytic amount of NaN₃ plays a crucial role in the reaction.

  已建立一种新型分子内氧化偶联反应，用于通过直接C(sp²)–H官能化形成C–O键制备苯并呋喃衍生物。此转化在无金属条件下由I₂/TBHP/NaN₃介导，而催化量的NaN₃在反应中起着关键作用。
• Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles
  作者：Stephane Pautus、Sook Wah Yee、Martyn Jayne、Michael P. Coogan、Claire Simons

  DOI：10.1016/j.bmc.2006.01.018

  日期：2006.6

  Methodology previously described by our group was applied to the preparation of a series of 4-alkyl/aryl-substituted 1-[benzofuran-2-yl-phenylmethyl]-1H-triazoles. The [1,2,4]-triazole derivatives were prepared for a range of alkyl and aryl substituents, and for the 4-methyl, 4-ethyl, 4-'propyl, 4-'butyl, 4-phenyl and 4-chlorophenyl derivatives, the minor [1,3,4]-triazole isomer also isolated. All the triazole derivatives were evaluated for CYP26A1 inhibitory activity using a MCF-7 cell-based assay. The 4-ethyl and 4-phenyl-1,2,4-triazole derivatives displayed inhibitory activity (IC50 4.5 and 7 mu M, respectively) comparable with that of the CYP26 inhibitor liarozole (IC50 7 mu M). Using a CYP26A1 homology model (based on CYP3A4) template, docking experiments were performed with MOE with multiple hydrophobic interactions observed in addition to coordination between the triazole nitrogen and the haem transition metal. (c) 2006 Elsevier Ltd. All rights reserved.