2-(4-羟基苯基)-1-苯基- | 82413-28-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-(4-羟基苯基)-1-苯基-
• 英文名称: 2-(4-Hydroxyphenyl)-1-phenylbutan-1-one
• CAS: 82413-28-3
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: FXJSXWBPLHSRGP-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87oC
• 沸点：
  391.0±17.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-羟基苯基)-1-苯基- 在 盐酸 、 硫酸 、 乙基溴化镁 作用下， 反应 14.0h， 生成 4-羟基他莫昔芬
  参考文献：
  名称：

  Estrogenic and antiestrogenic activity of monophenolic analogs of tamoxifen, [(Z)-2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine]

  摘要：

  Five hydroxylated analogues of tamoxifen [1, (Z)-2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine] and its geometric isomer were prepared by reaction of protected hydroxy-alpha-ethyldeoxybenzoins with 4-[2-dimethylamino) ethoxy]phenylmagnesium bromide, followed by acid-catalyzed dehydration-deprotection and chromatographic separation of isomer mixtures. Estrogen receptor binding affinity and estrogenic and antiestrogenic activity of each of the compounds were determined in the rat, in comparison with 4-hydroxytamoxifen (2). The new compounds had a wide range of receptor binding affinities, with that of 3-hydroxytamoxifen (6c), the most strongly bound, approaching that of estradiol. The trans isomers 6a,b were more strongly bound than were the cis isomers 7a,b. Antiestrogenic activity was seen in all compounds except 7b. This was also true for estrogenic activity, except that in 6c this activity was also substantially reduced. Maximal antiestrogenic effectiveness of 6c occurred at a 10-fold greater daily dose (50 micrograms/rat) than that required for maximal effect of 2.

  DOI：

  10.1021/jm00351a010
• 作为产物：
  描述：

  2-(p-甲氧基苯基) 在 氢溴酸 、 溶剂黄146 作用下， 反应 4.0h， 以82%的产率得到2-(4-羟基苯基)-1-苯基-
  参考文献：
  名称：

  Estrogenic and antiestrogenic activity of monophenolic analogs of tamoxifen, [(Z)-2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine]

  摘要：

  Five hydroxylated analogues of tamoxifen [1, (Z)-2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine] and its geometric isomer were prepared by reaction of protected hydroxy-alpha-ethyldeoxybenzoins with 4-[2-dimethylamino) ethoxy]phenylmagnesium bromide, followed by acid-catalyzed dehydration-deprotection and chromatographic separation of isomer mixtures. Estrogen receptor binding affinity and estrogenic and antiestrogenic activity of each of the compounds were determined in the rat, in comparison with 4-hydroxytamoxifen (2). The new compounds had a wide range of receptor binding affinities, with that of 3-hydroxytamoxifen (6c), the most strongly bound, approaching that of estradiol. The trans isomers 6a,b were more strongly bound than were the cis isomers 7a,b. Antiestrogenic activity was seen in all compounds except 7b. This was also true for estrogenic activity, except that in 6c this activity was also substantially reduced. Maximal antiestrogenic effectiveness of 6c occurred at a 10-fold greater daily dose (50 micrograms/rat) than that required for maximal effect of 2.

  DOI：

  10.1021/jm00351a010

文献信息

• The tin(II) enolate addition reactions to α, β-unsaturated ketones and quinones
  作者：Teruaki Mukaiyama、Nobuharu Iwasawa、Takeshi Yura、R.S.J. Clark

  DOI：10.1016/s0040-4020(01)87679-1

  日期：1987.1

  The reaction of tin(II) enolates with various α ,β-unsaturated carbonyl compounds is examined. When TMSCl is added as an activator of the α,β-unsaturated ketones, the Michael addition reaction proceeds smoothly to give the corresponding 1,4-adduct in good yield. When 1,4-benzoquinone and its mono-imino derivative are employed as acceptors in conjunction with dichloromethylsilane- DMAP activator, a

  研究了锡（II）烯醇化物与各种α，β-不饱和羰基化合物的反应。当加入TMSCl作为α，β-不饱和酮的活化剂时，迈克尔加成反应顺利进行，以良好的产率得到相应的1，4-加合物。当将1，4-苯醌及其单亚氨基衍生物与二氯甲基硅烷-DMAP活化剂一起用作受体时，发生新的加成-还原反应以提供α-芳基羰基化合物。
• A Convenient Preparation of α-(<i>p</i>-Hydroxy- or<i>p</i>-Aminophenyl) Carbonyl Compounds. Addition–Reduction Reaction of Tin(II) Enolate with p-Benzoquinone and Its Mono-<i>N</i>-tosylimino Derivative
  作者：Teruaki Mukaiyama、Richard S. J. Clark、Nobuharu Iwasawa

  DOI：10.1246/cl.1987.479

  日期：1987.3.5

  Tin(II) enolates react with p-benzoquinone and its mono-N-tosylimino derivative to give 1,2-adducts in good yield. These can be reduced in situ to α-(p-hydroxy- or p-aminophenyl) carbonyl derivatives by addition of dichloromethylsilane and dimethylaminopyridine.

  锡 (II) 烯醇化物与对苯醌及其单-N-甲苯磺酰亚氨基衍生物反应，以良好的产率得到 1,2-加合物。通过加入二氯甲基硅烷和二甲氨基吡啶，这些可以原位还原为 α-（对羟基或对氨基苯基）羰基衍生物。
• MUKAIYAMA TERUAKI; CLARK R. S. J.; IWASAWA NOBUHARU, CHEM. LETT.,(1987) N 3, 479-482
  作者：MUKAIYAMA TERUAKI、 CLARK R. S. J.、 IWASAWA NOBUHARU

  DOI：——

  日期：——
• US5026729A
  申请人：——

  公开号：US5026729A

  公开（公告）日：1991-06-25