6-methoxy-3-(4-methoxyphenyl)benzofuran | 52814-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 6-methoxy-3-(4-methoxyphenyl)benzofuran
• 英文别名: 6-Methoxy-3-(4-methoxyphenyl)-1-benzofuran
• CAS: 52814-52-5
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: QDOJXZISYFIEBV-UHFFFAOYSA-N

物化性质

• 熔点：
  225-226 °C (decomp)
• 沸点：
  398.7±37.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-3-(4-methoxyphenyl)benzofuran 在 吡啶盐酸盐 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 [6-hydroxy-3-(4-hydroxyphenyl)-1-benzofuran-2-yl](4-hydroxyphenyl)methanone
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. A study using triarylbutenone, benzofuran, and triarylfuran analogs as models for triarylethylenes and triarylpropenones

  摘要：

  In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constrained models for triarylethylene (TAE) and triarylpropenone (TAP) prototypes. The position-specific contributions of substituents to receptor affinity and to agonist-antagonist profiles were used as aids in characterizing the relative binding orientation of the prototypes. Although most compounds were found to be weak receptor ligands and poorly active in vivo, the following conclusions could be drawn about their SAR: (i) (Z)-TAPs and TAEs interact with the receptor in an analogous manner using the trans-stilbene core, with their agonist-antagonist profiles depending on the nature of other substructures. (ii) Incorporation into the benzofuran framework introduces a stereoelectronic constraint that compromises the normal binding interactions of TAE, as well as TAP, prototypes, resulting in their poor affinities and weak biological activities. (iii) (E)-TAPs can interact with the receptor through their S-cis conformation, but such a binding mode is unlikely to account for their behavior as antagonists.

  DOI：

  10.1021/jm00128a006
• 作为产物：
  描述：

  alpha-溴-4-甲氧基苯乙酮 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 6-methoxy-3-(4-methoxyphenyl)benzofuran
  参考文献：
  名称：

  3-芳基苯并呋喃、3-芳基苯并噻吩、2-芳基吲哚及其二聚体的简便合成

  摘要：

  摘要 描述了3-芳基苯并呋喃和苯并噻吩及其2-位二聚体和2-芳基吲哚及其3-位二聚体的制备。图形概要

  DOI：

  10.1080/00397911.2019.1611856

文献信息

• Ga(OTf)3-mediated synthesis of substituted benzofurans
  作者：Heui-Sin Wang、Chieh-Kai Chan、Meng-Yang Chang

  DOI：10.1016/j.tet.2016.07.007

  日期：2016.8

  intramolecular cyclodehydration of the resulting α-aryloxyaryl ketones, has been developed. The use of various metal triflates was investigated for a facile approach and efficient transformation. Pentacyclic benzophenanthrofurans 7 were prepared via photolytic annulations of 5.

  合成过程中，进行了一系列官能化的苯并呋喃的合成3 - 5个benzonaphthofurans 6，从α-溴代的分子间O-烷基化起始酮2与氢的氧化酚1，随后被Ga（OTF）3的催化的分子内的直接环化脱水已经开发了所得的α-芳氧基芳基酮。研究了各种金属三氟甲磺酸酯的使用，以实现简便的方法和有效的转化。通过5的光解法制备了五环二苯并呋喃7。
• Expanding the chemical space: Discovery of new anticancer <scp>3‐arylbenzofuran</scp> derivatives
  作者：Jinhwang Kim、Hyeon‐Min Cha、Mikyung Park、Dileep K. Singh、Gi H. Bae、Seong H. Kim、Ikyon Kim

  DOI：10.1002/jhet.4043

  日期：——

  amines and triethyl phosphite to give a wide variety of aminomethylphosphonates. Furthermore, several benzo[d]oxazoles and pyrrolo[1,2‐a]quinoxalines were prepared by using the formyl group. Biological screening of the synthesized compounds revealed that the benzofuran bearing a pyrrolo[1,2‐a]quinoxaline moiety (5b) most potently inhibited the viability of human blood cancer cells, but not solid tumor

  通过3-芳基苯并呋喃的C 2-官能化产生了一个新的化学空间。3-芳基苯并呋喃与仲胺和甲醛的曼尼希反应可将氨基甲基单元安装在苯并呋喃的C 2位。由Vilsmeier-Haack的3-芳基苯并呋喃甲酰化作用在C 2位引入的甲酰基被用作三组分Kabachnik-Fields与各种胺和亚磷酸三乙酯反应的反应伙伴，从而得到各种氨基甲基膦酸酯。此外，几种苯并[ d ]恶唑和吡咯并[1,2- a通过使用甲酰基制备]喹喔啉。对合成化合物的生物学筛选显示，带有吡咯并[1,2- a ]喹喔啉部分（5b）的苯并呋喃最能抑制人类血液癌细胞的活力，但不能抑制实体瘤细胞的活力。Caspase活性测定，膜联蛋白V阳性细胞分析和蛋白质印迹分析表明，5b诱导的人淋巴瘤U937细胞死亡可能是由于其具有通过抑制ERK激活来诱导血癌细胞caspase依赖性凋亡而导致的。
• 10.1055/s00401705985
  作者：Kim, Sung June、Lee, Sunhee、Kim, Ikyon

  DOI：10.1055/s00401705985

  日期：——
• 488. Furano-compounds. Part XI. The synthesis of α-anhydro-O-trimethylbrazilone and related compounds
  作者：P. C. Johnson、Alexander Robertson

  DOI：10.1039/jr9500002381

  日期：——
• DURANI, NEELAM;JAIN, RAKA;SAEED, ASHRAF;DIKSHIT, DINESH K.;DURANI, SUSHEE+, J. MED. CHEM., 32,(1989) N, C. 1700-1707
  作者：DURANI, NEELAM、JAIN, RAKA、SAEED, ASHRAF、DIKSHIT, DINESH K.、DURANI, SUSHEE+

  DOI：——

  日期：——