1,1-bis(4-hydroxyphenyl)methylenecyclopentane | 66422-10-4

• 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: 1,1-bis(4-hydroxyphenyl)methylenecyclopentane
• 英文别名: 2,2-bis(4-hydroxyphenyl)methylenecyclopentane；[bis(4-hydroxyphenyl)methylene]cyclopentane；4,4'-(cyclopentylidenemethylene)diphenol；Bis-(4-hydroxy-phenyl)-cyclopentyliden-methan；Cyclopentyliden-bis-(4-hydroxy-phenyl)-methan；4-Cyclopentyliden(4-hydroxyphenyl)methylphenol；4-[cyclopentylidene-(4-hydroxyphenyl)methyl]phenol
• CAS: 66422-10-4
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: GIGYKXHGYNZBEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1,1-bis(4-hydroxyphenyl)methylenecyclopentane 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 26.0h， 生成 4-((4-((6-(bis(pyridin-2-ylmethyl)amino)hexyl)oxy)phenyl)(cyclopentylidene)methyl)phenol
  参考文献：
  名称：

  Design, synthesis, and evaluation of cyclofenil derivatives for potential SPECT imaging agents

  摘要：

  To develop technetium- and rhenium-labeled nonsteroidal estrogen imaging agents for estrogen receptor (ER) positive breast tumors, two groups of rhenium and technetium cyclofenil derivatives were synthesized and characterized. The binding affinities of the rhenium complexes for ERs were determined. The tricarbonyl rhenium complex showed the highest binding affinity for ERs (81.2 for ER beta, 16.5 for ER alpha). Tricarbonyl technetium cyclofenil complexes were obtained in high radiochemical purity and radiochemical yields. The results of studies of their octanol/water partition and in vitro stability are presented. These results demonstrate that these radiolabeled cyclofenil derivatives may be considered as potential breast cancer imaging agents.

  DOI：

  10.1007/s00775-010-0627-0
• 作为产物：
  描述：

  环戊烷甲酸甲酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 1,1-bis(4-hydroxyphenyl)methylenecyclopentane
  参考文献：
  名称：

  Synthesis of Unsymmetrical Diphenylalkenes¹

  摘要：

  DOI：

  10.1021/jm00342a033

文献信息

• Catalytic Enantioselective House–Meinwald Rearrangement: Efficient Construction of All-Carbon Quaternary Stereocenters
  作者：Dengke Ma、Chun-Bao Miao、Jianwei Sun

  DOI：10.1021/jacs.9b07514

  日期：2019.9.4

  A catalytic asymmetric House‒Meinwald rearrangement for the synthesis of both cyclic and acyclic ketones is disclosed. From readily accessible racemic tetrasubstituted epoxides, this approach provides efficient access to chiral ketones bearing α all-carbon quaternary stereocenters with high enantiocontrol. The observation of positive non-linear effects and nontrivial kinetic feature provided important

  公开了一种用于合成环状酮和无环酮的催化不对称 House-Meinwald 重排。从容易获得的外消旋四取代环氧化物中，这种方法提供了有效获取带有 α 全碳四元立体中心且具有高对映控制的手性酮的途径。对正非线性效应和非平凡动力学特征的观察提供了对该机制的重要见解。
• Fluorine-Substituted Cyclofenil Derivatives as Estrogen Receptor Ligands:  Synthesis and Structure−Affinity Relationship Study of Potential Positron Emission Tomography Agents for Imaging Estrogen Receptors in Breast Cancer
  作者：Jai Woong Seo、John S. Comninos、Dae Yoon Chi、Dong Wook Kim、Kathryn E. Carlson、John A. Katzenellenbogen

  DOI：10.1021/jm0512037

  日期：2006.4.1

  In a search for estrogen receptor (ER) ligands to be radiolabeled with fluorine-18 for imaging of ER-positive breast tumors with positron emission tomography (PET), we investigated cyclofenil analogues substituted at the C3 or C4 position of the cyclohexyl group. McMurry coupling of 4,4'-dihydroxybenzophenone with various ketones produced key cyclofenil intermediates, from which C3 and C4 substituents

  在寻找用氟 18 放射性标记的雌激素受体 (ER) 配体，以便通过正电子发射断层扫描 (PET) 对 ER 阳性乳腺肿瘤进行成像时，我们研究了在环己基的 C3 或 C4 位置取代的环芬尼类似物。4,4'-二羟基二苯甲酮与各种酮的 McMurry 偶联产生了关键的环芬尼中间体，其中含有烷基和各种氧或氟取代的烷基的 C3 和 C4 取代基被精心设计。对 ERα 和 ERβ 的结合测定表明，C3 位点比 C4 位点更能耐受空间体积和极性基团，这与 ERα 配体结合袋的计算模型一致。氟取代在某些位点的耐受性非常好，使得一些化合物的亲和力与雌二醇相当或更高。这些氟和氟烷基环芬尼尔值得进一步考虑作为氟 18 标记的 ER 配体，用于乳腺肿瘤 ER 的 PET 成像。
• A novel tamoxifen derivative, ridaifen-F, is a nonpeptidic small-molecule proteasome inhibitor
  作者：Makoto Hasegawa、Yukari Yasuda、Makoto Tanaka、Kenya Nakata、Eri Umeda、Yanwen Wang、Chihiro Watanabe、Shoko Uetake、Tatsuki Kunoh、Masafumi Shionyu、Ryuzo Sasaki、Isamu Shiina、Tamio Mizukami

  DOI：10.1016/j.ejmech.2013.11.009

  日期：2014.1

  In a survey of nonpeptide noncovalent inhibitors of the human 20S proteasome, we found that a novel tamoxifen derivative, RID-F (compound 6), inhibits all three protease activities of the proteasome at submicromolar levels. Structure activity relationship studies revealed that a RID-F analog (RID-F-S*4, compound 25) is the smallest derivative compound capable of inhibiting proteasome activity, with a potency similar to that of RID-F. Kinetic analyses of the inhibition mode and competition experiments involving biotin-belactosin A (a proteasome inhibitor) binding indicated that the RID-F derivatives interact with the protease subunits in a different manner. Culturing of human cells with these compounds resulted in accumulation of ubiquitinated proteins and induction of apoptosis. Thus, the RID-F derivatives may be useful lead chemicals for the generation of a new class of proteasome inhibitors. (C) 2013 Elsevier Masson SAS. All rights reserved.
• 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.