N-(3,4-dimethoxyphenyl)benzofuran-2-carboxamide | 345991-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3,4-dimethoxyphenyl)benzofuran-2-carboxamide
• 英文别名: N-(3,4-dimethoxyphenyl)-1-benzofuran-2-carboxamide
• CAS: 345991-36-8
• 化学式: C₁₇H₁₅NO₄
• mdl: MFCD01179908
• 分子量: 297.31
• InChiKey: TWFIJOFWVNYTBL-UHFFFAOYSA-N

物化性质

• 溶解度：
  7.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(3,4-dimethoxybenzyl)benzofuran 在 叠氮基三甲基硅烷 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 iron(II) chloride 作用下， 以 水 为溶剂， 反应 12.0h， 以71%的产率得到N-(3,4-dimethoxyphenyl)benzofuran-2-carboxamide
  参考文献：
  名称：

  Pd-Catalyzed Isocyanide Assisted Reductive Cyclization of 1-(2-Hydroxyphenyl)-propargyl Alcohols for 2-Alkyl/Benzyl Benzofurans and Their Useful Oxidative Derivatization

  摘要：

  An unusual Pd-catalyzed isocyanide assisted 5exo-dig reductive cyclization of 1-(2-hydroxyphenyl)-propargyl alcohols is achieved for 2-alkyl/benzyl benzofurans. The reaction features a high substrate scope, insensitivity to air, and excellent product yielding. Further, a direct metal-free C-H functionalization (azidation, alkoxylation, and hydroxylation) and selective oxidative cleavage of thus synthesized 2-benzylfurans are described for azido-, alkoxy-, hydroxyl-, amide-, and tetrazolyl adducts.

  DOI：

  10.1021/acs.joc.5b02204

文献信息

• Design, synthesis, and biological evaluation of benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents and inhibitors of NF-κB
  作者：Minho Choi、Hyeju Jo、Hyun-Jung Park、Arepalli Sateesh Kumar、Joonkwang Lee、Jieun Yun、Youngsoo Kim、Sang-bae Han、Jae-Kyung Jung、Jungsook Cho、Kiho Lee、Jae-Hwan Kwak、Heesoon Lee

  DOI：10.1016/j.bmcl.2015.04.050

  日期：2015.6

  potentiated the anticancer activity and NF-κB inhibitory activity, respectively. However, according to the results of structure–activity relationship studies, only benzofuran-2-carboxylic acid N-(4′-hydroxy)phenylamide (3m) was the lead scaffold with both an outstanding anticancer activity and NF-κB inhibitory activity. This novel lead scaffold may be helpful for investigation of new anticancer agents that act

  为了开发新型支架作为抗癌剂和NF-κB活性抑制剂，开发了60种新颖的苯并呋喃和2,3-二氢苯并呋喃-2-羧酸N-（取代）苯酰胺衍生物（1a - s，2a - k，3a – s和4a – k）是由参考铅化合物KL-1156设计和合成的，它是LPS刺激的RAW 264.7巨噬细胞中NF-κB易位至细胞核的抑制剂。新型苯并呋喃-和2,3-二氢苯并呋喃-2-羧酰胺衍生物在低微摩尔浓度下对六种人类癌细胞系表现出强力的细胞毒性活性（通过磺基罗丹明B测定）：ACHN（肾），HCT15（结肠），MM231（乳腺），NUGC-3（胃），NCI-H23（肺）和PC-3（前列腺）。此外，这些化合物还抑制LPS诱导的NF-κB转录活性。N-苯环上的+ M效应和疏水基团分别增强了其抗癌活性和NF-κB抑制活性。然而，根据结构-活性关系研究的结果，只有苯并呋喃-2-羧酸N-（4'-羟基）苯酰胺（3m）是具有出色的抗癌
• Synthesis of benzofuranyl and indolyl methyl azides by tandem silver-catalyzed cyclization and azidation
  作者：Gadi Ranjith Kumar、Yalla Kiran Kumar、Ruchir Kant、Maddi Sridhar Reddy

  DOI：10.1039/c6ob00191b

  日期：——

  Ag(I)-catalyzed synthesis of 2-azidomethyl benzofurans/indoles from linear and readily available hydroxyl/amino-phenyl propargyl alcohols is described via a highly regioselective C–O and C–N bond formation. Control experiments reveal that the reaction involves the sequential Ag(I)-catalyzed 5-exo-dig cyclization and a catalyst free γ-allylic azidation. The synthetic utility of this method has been

  通过高度区域选择性的C-O和C-N键的形成，描述了Ag（I）催化的由线性和容易获得的羟基/氨基苯基炔丙基醇合成2-叠氮甲基苯并呋喃/吲哚的过程。对照实验表明，该反应涉及顺序的Ag（I）催化的5 -exo-dig环化和无催化剂的γ-烯丙基叠氮化。通过将上述合成的杂环的叠氮甲基单元用作各种其他官能化的基础，例如三唑-，四唑-，酰胺-，胺-和吡啶基-衍生物，已经证明了该方法的合成效用。
• Pd-Catalyzed Isocyanide Assisted Reductive Cyclization of 1-(2-Hydroxyphenyl)-propargyl Alcohols for 2-Alkyl/Benzyl Benzofurans and Their Useful Oxidative Derivatization
  作者：Manda Rajesh、Nuligonda Thirupathi、Thota Jagadeshwar Reddy、Sanjeev Kanojiya、Maddi Sridhar Reddy

  DOI：10.1021/acs.joc.5b02204

  日期：2015.12.18

  An unusual Pd-catalyzed isocyanide assisted 5exo-dig reductive cyclization of 1-(2-hydroxyphenyl)-propargyl alcohols is achieved for 2-alkyl/benzyl benzofurans. The reaction features a high substrate scope, insensitivity to air, and excellent product yielding. Further, a direct metal-free C-H functionalization (azidation, alkoxylation, and hydroxylation) and selective oxidative cleavage of thus synthesized 2-benzylfurans are described for azido-, alkoxy-, hydroxyl-, amide-, and tetrazolyl adducts.