2-(4-hydroxyphenyl)-1-(4-methoxyphenyl)butan-1-one | 52803-48-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-hydroxyphenyl)-1-(4-methoxyphenyl)butan-1-one
• 英文别名: 1-(4-Methoxyphenyl)-2-(4-hydroxyphenyl)-butan-1-on；1-<4-Methoxy-phenyl>-2-<4-hydroxy-phenyl>-butanon-1；2-(4-Hydroxy-phenyl)-1-(4-methoxy-phenyl)-butan-1-on
• CAS: 52803-48-2
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: IFWKFWILOIIIRA-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  444.5±25.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-1-(4-methoxyphenyl)butan-1-one 在 盐酸 、 正丁基锂 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 环己烷 为溶剂， 反应 3.08h， 生成 1-(4-methoxyphenyl)-2-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-1-(6-methoxynaphthalen-2-yl)butene
  参考文献：
  名称：

  In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor☆

  摘要：

  There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphenylnaphthyl propylene ligand 1. All compounds gave K(j)s under 10 nM when assayed in the presence of ERalpha. Generally these compounds had very high affinity for both ER isotypes. Moving the hydroxyl group on naphthalene from the 6- to the 5-position of the alpha-naphthalene attached compounds (6b and 6e vs 6c and 6f) had little affect on ER binding nor did altering the position of the naphthalene attachment (alpha or beta) to the alkene moiety. In transfection assays none of the compounds displayed agonistic activity in the absence of E-2. In MCF-7 proliferation assays 6a-d, 6f and 12a-c successfully abrogated E-2 stimulation and resulted in greater than 50% inhibition at 1 muM, a level of efficacy similar to that obtained when the cells were treated with raloxifene. Our results show that this new class of SERMs are good candidates for further study as therapeutic agents for the treatment of breast cancer and osteoporosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.051
• 作为产物：
  描述：

  6-甲氧基-2-(4-苯甲氧基)苯并噻吩 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2-(4-hydroxyphenyl)-1-(4-methoxyphenyl)butan-1-one
  参考文献：
  名称：

  In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor☆

  摘要：

  There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphenylnaphthyl propylene ligand 1. All compounds gave K(j)s under 10 nM when assayed in the presence of ERalpha. Generally these compounds had very high affinity for both ER isotypes. Moving the hydroxyl group on naphthalene from the 6- to the 5-position of the alpha-naphthalene attached compounds (6b and 6e vs 6c and 6f) had little affect on ER binding nor did altering the position of the naphthalene attachment (alpha or beta) to the alkene moiety. In transfection assays none of the compounds displayed agonistic activity in the absence of E-2. In MCF-7 proliferation assays 6a-d, 6f and 12a-c successfully abrogated E-2 stimulation and resulted in greater than 50% inhibition at 1 muM, a level of efficacy similar to that obtained when the cells were treated with raloxifene. Our results show that this new class of SERMs are good candidates for further study as therapeutic agents for the treatment of breast cancer and osteoporosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.051

文献信息

• C-C-Spaltung eines 1,2-diarylsubstituierten Ketoxims bei der Umsetzung mit Äthylmagnesiumbromid
  作者：H. Hamacher

  DOI：10.1002/ardp.19743070412

  日期：——

  Diazotieren von 1‐(4‐Methoxyphenyl‐2‐(4‐aminophenyl)‐butan‐1‐on (4) und Erhitzen der Diazoniumsalzlösung wird 1‐(4(Methoxyphenyl)‐2‐(4‐hydroxyphenyl)‐butan‐1‐on (5) dargestellt und dieses mit Hydroxylamin in 1‐(4‐Methoxy‐phenyl)‐1‐hydroximino‐2‐(4‐hydroxyphenyl)‐butan (6) überführt. Bei der Umsetzung von 6 mit Äthylmagnesiumbromid tritt nicht die von anderen Aryl‐alkyl‐ketoximen bekannte Cyclisierung zum entsprechenden

  重氮化 1-(4-甲氧基苯基-2-(4-氨基苯基)-丁烷-1-一(4)并加热重氮盐溶液得到1-(4-甲氧基苯基)-2-(4-羟基苯基)-丁烷-1 -在 (5) 上，这与羟胺转化为 1- (4- 甲氧基 - 苯基) -1- 羟基- 2- (4- 羟苯基) - 丁烷 (6) 环化反应，从其他芳基烷基酮肟中已知，得到相应的氮丙啶衍生物 3. 相反，6 在 C-1 和 C-2 之间裂解形成 4-甲氧基苯甲腈 (7) 和反-4-丙烯基苯酚 8。
• Diethylstilbestrol and its Monomethyl Ether
  作者：A. L. Wilds、Warren R. Biggerstaff

  DOI：10.1021/ja01221a029

  日期：1945.5
• In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor☆
  作者：Jonathan M. Schmidt、Gilles B. Tremblay、Michael A. Plastina、Fupeng Ma、Sanjivanjit Bhal (neé Basra)、Miklos Feher、Robert Dunn-Dufault、Peter R. Redden

  DOI：10.1016/j.bmc.2004.11.051

  日期：2005.3.1

  There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphenylnaphthyl propylene ligand 1. All compounds gave K(j)s under 10 nM when assayed in the presence of ERalpha. Generally these compounds had very high affinity for both ER isotypes. Moving the hydroxyl group on naphthalene from the 6- to the 5-position of the alpha-naphthalene attached compounds (6b and 6e vs 6c and 6f) had little affect on ER binding nor did altering the position of the naphthalene attachment (alpha or beta) to the alkene moiety. In transfection assays none of the compounds displayed agonistic activity in the absence of E-2. In MCF-7 proliferation assays 6a-d, 6f and 12a-c successfully abrogated E-2 stimulation and resulted in greater than 50% inhibition at 1 muM, a level of efficacy similar to that obtained when the cells were treated with raloxifene. Our results show that this new class of SERMs are good candidates for further study as therapeutic agents for the treatment of breast cancer and osteoporosis. (C) 2004 Elsevier Ltd. All rights reserved.

表征谱图