3-methyl[bis(4-hydroxyphenyl)methylene]cyclohexane | 1242078-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl[bis(4-hydroxyphenyl)methylene]cyclohexane
• CAS: 1242078-21-2
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: QUCLTMSWCMCJJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-methyl[bis(4-hydroxyphenyl)methylene]cyclohexane 、 对甲苯磺酸氟乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3-methyl[(4-(2-fluoroethoxy)phenyl)-(4-hydroxyphenyl)methylene]cyclohexane
  参考文献：
  名称：

  Synthesis and evaluation of fluoroethyl cyclofenil analogs: Models for potential estrogen receptor imaging agent

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2012.04.005
• 作为产物：
  描述：

  4,4'-二羟基二苯甲酮 、 3-甲基环己酮 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到3-methyl[bis(4-hydroxyphenyl)methylene]cyclohexane
  参考文献：
  名称：

  Practical Synthesis of FEt-penta-cyclofenil and Its Derivatives for Potential PET Imaging

  摘要：

  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.

  DOI：

  10.1080/00397910903419829

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.