1-<2-hydroxy-4-<(tetrahydropyran-2-yl)oxy>phenyl>-2-phenylethanone | 130064-20-9

• 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: 1-<2-hydroxy-4-<(tetrahydropyran-2-yl)oxy>phenyl>-2-phenylethanone
• 英文别名: 1-(2-hydroxy-4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-phenylethanone；1-[2-Hydroxy-4-(oxan-2-yloxy)phenyl]-2-phenylethanone
• CAS: 130064-20-9
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: CKDRTHDAINOTDY-UHFFFAOYSA-N

物化性质

• 熔点：
  89°C
• 沸点：
  506.0±50.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<2-hydroxy-4-<(tetrahydropyran-2-yl)oxy>phenyl>-2-phenylethanone 在 哌啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 苯 为溶剂， 反应 12.0h， 生成 2-(4-hydroxyphenyl)-3-phenyl-7-<(tetrahydropyran-2-yl)oxy>-2H-1-benzopyran
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. Phenolic analogs of 2,3-diaryl-2H-1-benzopyrans

  摘要：

  Phenolic analogues of 2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran (1), a novel antiestrogen, were synthesized and evaluated for their structure-activity relationship. Incorporation of OH at position 7 was found to improve receptor affinity of the benzopyran while having no effect on its action as an antagonist. Similar substitution of 2-phenyl as well potentiated receptor affinity as well as antagonist activity of the prototype. The monophenol 19 and the diphenol 25 were thus found to be good receptor ligands, devoid of estrogen agonist activity and associated with marked antiestrogenic activity of comparable order. Both caused nearly complete inhibition of the estradiol stimulated uterine growth in rats as well as mice and were thus found to be better antiestrogens than tamoxifen, trioxifen, and LY-117018. A binding-site model for estrogen receptor rationalizing the structure-activity relationship of benzopyrans in relation to that of the triarylethylene and the triarylpropenone antiestrogens has been discussed.

  DOI：

  10.1021/jm00174a020
• 作为产物：
  描述：

  间苯二酚 在 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 16.0h， 生成 1-<2-hydroxy-4-<(tetrahydropyran-2-yl)oxy>phenyl>-2-phenylethanone
  参考文献：
  名称：

  ANTI-ESTROGENIC COMPOUNDS

  摘要：

  本公开提供一种具有以下化学式的化合物：或其药用可接受盐，其中X、R1-R8、Y1-Y5、m、n、p和q在此处定义。这些新型2H-香豆素化合物对通过雌激素介导的疾病和其他疾病的调节具有用处，如本文所述。本发明还涉及含有这些化合物的药物组合物以及使用这些化合物和组合物的方法。

  公开号：

  US20160311805A1

文献信息

• An Efficient Process for the Synthesis of trans-2,3-Disubstituted-2,3-dihydro-4H-1-benzopyran-4-ones (Chroman-4-ones)
  作者：Richard W. Draper、Bin Hu、Radha V. Iyer、Xun Li、Yuelie Lu、Mohammad Rahman、Eugene J. Vater

  DOI：10.1016/s0040-4020(00)00101-0

  日期：2000.3

  The piperidine catalyzed Knoevenagel condensation of 2'-aryl/alkyl-2-hydroxyacetophenones 7 and aryl/alkylaldehydes 8 in refluxing isopropyl alcohol with azeotropic removal of water affords, in high yield, equilibrium mixtures of E- and Z-chalcones 9 and cis- and trans-chroman-4-ones 10 which are effectively isomerized in situ to the trans-2,3-diaryl/alkylchroman-4-ones, following the addition of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) to the cooled reaction mixture and may be isolated in high purities (91-99%) by simple filtration, with good to excellent yields (70-95%). (C) 2000 Elsevier Science Ltd. All rights reserved.
• SHARMA, ARUN P.;SAEED, ASHRAF;DURANI, SUSHEEL;KAPIL, RANDHIR S., J. MED. CHEM., 33,(1990) N2, C. 3222-3229
  作者：SHARMA, ARUN P.、SAEED, ASHRAF、DURANI, SUSHEEL、KAPIL, RANDHIR S.

  DOI：——

  日期：——
• [EN] ANTI-ESTROGENIC COMPOUNDS<br/>[FR] COMPOSÉS ANTI-ŒSTROGÉNIQUES
  申请人：PFIZER

  公开号：WO2016174551A1

  公开（公告）日：2016-11-03

  The present disclosure provides a compound of Formula (I): or a pharmaceutically acceptable salt wherein X, R1-R8, Υ1-Υ5, m, n, p, and q are defined herein. The novel 2H-chromene compounds are useful for the modulation of disorders mediated by estrogen, and other disorders, as described herein. The present invention also relates to pharmaceutical compositions containing the compounds and to methods of using the compounds and compositions.