4-[1-(4-羟基苯基)-3-甲基丁-1-烯基]苯酚 | 66422-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[1-(4-羟基苯基)-3-甲基丁-1-烯基]苯酚
• 英文名称: 1,1-bis(4-hydroxyphenyl)-3-methyl-1-butene
• 英文别名: iso-[bis(4-hydroxyphenyl)methylene]butane；1,1-Bis-(4-hydroxy-phenyl)-3-methyl-but-1-en；Phenol, 4,4'-(3-methyl-1-butenylidene)bis-；4-[1-(4-hydroxyphenyl)-3-methylbut-1-enyl]phenol
• CAS: 66422-07-9
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: DDEWRRMILVWZOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[1-(4-羟基苯基)-3-甲基丁-1-烯基]苯酚 、 二异丙氨基乙基氯盐酸盐 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 N-[2-[4-[1-[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-3-methylbut-1-enyl]phenoxy]ethyl]-N-propan-2-ylpropan-2-amine
  参考文献：
  名称：

  Cytotoxicity and Antiestrogenicity of a Novel Series of Basic Diphenylethylenes

  摘要：

  On the premise that it is necessary to develop antiestrogens with a higher cytotoxic component in order to reduce the risks of the development of heterogeneous malignant cell populations in breast cancer, we studied a novel series of basic diphenylethylenes, for the most part devoid of estrogenic activity, with low antiestrogenicity but much enhanced cytotoxicity compared to the reference drug tamoxifen. The main structural features associated with cytotoxicity were E isomery, substituents of five to eight carbons on the ethylene bond, and dibasicity.

  DOI：

  10.1021/jm950624t
• 作为产物：
  描述：

  1,1-bis(4-methoxyphenyl)-3-methyl-1-butene 在 吡啶盐酸盐 作用下， 反应 0.75h， 以85%的产率得到4-[1-(4-羟基苯基)-3-甲基丁-1-烯基]苯酚
  参考文献：
  名称：

  Cytotoxicity and Antiestrogenicity of a Novel Series of Basic Diphenylethylenes

  摘要：

  On the premise that it is necessary to develop antiestrogens with a higher cytotoxic component in order to reduce the risks of the development of heterogeneous malignant cell populations in breast cancer, we studied a novel series of basic diphenylethylenes, for the most part devoid of estrogenic activity, with low antiestrogenicity but much enhanced cytotoxicity compared to the reference drug tamoxifen. The main structural features associated with cytotoxicity were E isomery, substituents of five to eight carbons on the ethylene bond, and dibasicity.

  DOI：

  10.1021/jm950624t

文献信息

• Practical Synthesis of FEt-penta-cyclofenil and Its Derivatives for Potential PET Imaging
  作者：Hua Zhu、Liliang Huang、Xiaoping Xu、Yu-Mei Shen

  DOI：10.1080/00397910903419829

  日期：2010.10.20

  Generally, FEt-penta-cyclofenil and its derivatives have greater relative binding affinity to estradiol receptors than estradiol. (4-Fluoroethoxyphenyl)-(4'-hydroxyphenyl) methylenecyclopentane and its derivatives were synthesized for potential radioactive image agents, and their structures were characterized by ultraviolet, infrared, 1H NMR, 19F NMR, and high-resolution mass spectrometry.
• Synthesis and evaluation of fluoroethyl cyclofenil analogs: Models for potential estrogen receptor imaging agent
  作者：Hua Zhu、Zhi Yang、Jian-Guo Lin、Shi-Neng Luo、Yu-Mei Shen

  DOI：10.1016/j.jfluchem.2012.04.005

  日期：2012.7

  Cyclofenil analogs (2a-2f) and their fluorine-containing derivatives (3a-3f) were synthesized and evaluated as candidate ligands for positron emission tomography (PET) imaging of estrogen receptors. Most of them show relatively high binding affinities comparable with estradiol (E-2). (4-Fluoroethoxyphenyl)-(4-hydroxyphenyl) methylenecyclopentane (3a) showed both the highest binding affinity for ERs (88.6 for ER beta, 13.8 for ER alpha) and highest beta/alpha ratio (beta/alpha for 6.4-fold). The radioactive compound [F-18]3a was prepared via displacement of the corresponding mesylate precursor 4 with [F-18]fluoride (F-18: beta(+): 96.7%, T-1/2 = 109.8 min). The biodistribution studies in immature female SD rats demonstrated that the uptake in the uterus and ovaries were 1.358 +/- 0.089% ID/g, 1.439 +/- 0.214% ID/g, respectively, both of the ratios of uterus/blood and ovaries/blood was less than 2:1. Micro-PET imaging of immature female SD rats has also been reported. (C) 2012 Elsevier B.V. All rights reserved.
• Cytotoxicity and Antiestrogenicity of a Novel Series of Basic Diphenylethylenes
  作者：Jacques Gilbert、Maryse Fuentes、Tiiu Ojasoo、Jean-Christophe Doré、Michel Pons

  DOI：10.1021/jm950624t

  日期：1997.3.1

  On the premise that it is necessary to develop antiestrogens with a higher cytotoxic component in order to reduce the risks of the development of heterogeneous malignant cell populations in breast cancer, we studied a novel series of basic diphenylethylenes, for the most part devoid of estrogenic activity, with low antiestrogenicity but much enhanced cytotoxicity compared to the reference drug tamoxifen. The main structural features associated with cytotoxicity were E isomery, substituents of five to eight carbons on the ethylene bond, and dibasicity.