(4,4'-dimethoxy-benzhydrylidene)adamantane | 23571-06-4

• 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: (4,4'-dimethoxy-benzhydrylidene)adamantane
• 英文别名: di-p.methoxy phenyl adamantylidene methane；2-[Bis(4-methoxyphenyl)methylidene]adamantane
• CAS: 23571-06-4
• 化学式: C₂₅H₂₈O₂
• 分子量: 360.496
• InChiKey: YFYLAGWKOQZLEP-UHFFFAOYSA-N

物化性质

• 沸点：
  523.7±30.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4,4'-dimethoxy-benzhydrylidene)adamantane 在 二甲基硫 、 三氟化硼 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到4,4'-((1r,3r,5r,7r)-adamantan-2-ylidenemethylene)diphenol
  参考文献：
  名称：

  Bridged Bicyclic Cores Containing a 1,1-Diarylethylene Motif Are High-Affinity Subtype-Selective Ligands for the Estrogen Receptor

  摘要：

  The actions of estrogens are mediated through the two estrogen receptors, ERalpha and ERbeta. Compounds that interact selectively with ERalpha or ERbeta are of interest because they could be used to explore the biological roles of these ER subtypes and they might be interesting estrogen pharmaceuticals. In a new approach to develop ER subtype-selective ligands, we have embellished the 1,1-diarylethylene motif, common to many nonsteroidal estrogens, with various bridged bicyclic or tricyclic cores, including ones based on bicyclo [3.3.1] nonane, bicyclo [2.2.1] heptane, and selected bi- and tricyclic terpenoids. This design leads to three-dimensional ER ligands of unusual structure that we have used to probe the size and shape of the ligand binding pocket of ERalpha and ERbeta. Many of these compounds have high binding affinities, with the best having a bicyclo[3.3.1]nonane core and binding 3-5 times better than estradiol to both ER subtypes. Some of the compounds show significant affinity selectivity in favor of ERbeta (4- to 5-fold), and in cell-based assays for transcriptional activity most are partial agonists on ERalpha and full antagonists on ERbeta.

  DOI：

  10.1021/jm0204800
• 作为产物：
  描述：

  金刚烷酮 、 4,4'-二甲氧基二苯甲酮 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以54%的产率得到(4,4'-dimethoxy-benzhydrylidene)adamantane
  参考文献：
  名称：

  Bridged Bicyclic Cores Containing a 1,1-Diarylethylene Motif Are High-Affinity Subtype-Selective Ligands for the Estrogen Receptor

  摘要：

  The actions of estrogens are mediated through the two estrogen receptors, ERalpha and ERbeta. Compounds that interact selectively with ERalpha or ERbeta are of interest because they could be used to explore the biological roles of these ER subtypes and they might be interesting estrogen pharmaceuticals. In a new approach to develop ER subtype-selective ligands, we have embellished the 1,1-diarylethylene motif, common to many nonsteroidal estrogens, with various bridged bicyclic or tricyclic cores, including ones based on bicyclo [3.3.1] nonane, bicyclo [2.2.1] heptane, and selected bi- and tricyclic terpenoids. This design leads to three-dimensional ER ligands of unusual structure that we have used to probe the size and shape of the ligand binding pocket of ERalpha and ERbeta. Many of these compounds have high binding affinities, with the best having a bicyclo[3.3.1]nonane core and binding 3-5 times better than estradiol to both ER subtypes. Some of the compounds show significant affinity selectivity in favor of ERbeta (4- to 5-fold), and in cell-based assays for transcriptional activity most are partial agonists on ERalpha and full antagonists on ERbeta.

  DOI：

  10.1021/jm0204800

文献信息

• Adamantylene compounds
  申请人：U.S. Philips Corporation

  公开号：US03936491A1

  公开（公告）日：1976-02-03

  Substituted diphenyl adamantylidene methanes. Examples of substituents on the para positions of the phenyl groups are propoxy and acetyloxy. The compounds have estrogenic activities.

  取代二苯基金刚烷亚甲基甲烷。苯基上的对位取代基的例子包括丙氧基和乙酰氧基。这些化合物具有雌激素活性。
• Catalytic Epoxidation of Hindered Olefins with Dioxygen. Fast Oxygen Atom Transfer to Olefin Cation Radicals from Nitrogen Oxides
  作者：Eric Bosch、Jay K. Kochi

  DOI：10.1021/ja953786n

  日期：1996.1.1

  efficiently converted to epoxides by dioxygen at 25 °C in dichloromethane containing catalytic amounts of nitrogen oxides (NO2, NO+, NO, etc.). Nitrogen dioxide also effects the direct (stoichiometric) epoxidation of the same hindered olefins. Olefin cation radicals are spectrally identified as the first observable intermediate, and separate experiments confirm the facile transfer of an oxygen atom from nitrogen

  受阻烯烃在 25 °C 下通过分子氧在含有催化量氮氧化物（NO2、NO+、NO 等）的二氯甲烷中有效转化为环氧化物。二氧化氮还影响相同受阻烯烃的直接（化学计量）环氧化。烯烃阳离子自由基被光谱鉴定为第一个可观察到的中间体，单独的实验证实氧原子从二氧化氮轻松转移到烯烃阳离子自由基以产生环氧化物。在低温 (-78 °C) 下，添加 1-电子氧化剂如三 (2,4-二溴苯基) 胺阳离子自由基和亚硝 (NO+) 会迅速引发环氧化反应。方案 3 展示了氧化还原变化的完整序列，在受阻烯烃通过阳离子自由基催化转化为环氧化物的过程中，氧化还原变化由氮氧化物介导。
• Efficient Hydrogenation of Sterically Hindered Olefins with Borane−Methyl Sulfide Complex
  作者：R. Rathore、U. Weigand、J. K. Kochi

  DOI：10.1021/jo960357e

  日期：1996.1.1

  Sterically hindered olefins are efficiently reduced to the corresponding alkanes by the borane-methyl sulfide (BMS) complex at room temperature (or below) in dichloromethane containing a mild one-electron oxidant (such as an aromatic cation radical) or by the passage of an anodic current. In an alternative procedure, the hydrogenation of the same (electron-rich) olefins with the EMS complex (in the absence of a one-electron oxidant) is also carried out-in the presence of a strong Bronsted acid (such as HBF4). In the oxidative activation, olefin cation radicals are the first observable intermediates, and separate experiments (including transient electrochemistry) confirm the facile reduction of the olefin cation radical by borane to produce the corresponding alkane. The direct protonation of olefins produces carbocationic intermediates which are also efficiently reduced by borane to the corresponding alkanes. The intermediacy of both olefin cation radicals and carbocations in the hydrogenation procedure with borane is discussed.
• US3936491A
  申请人：——

  公开号：US3936491A

  公开（公告）日：1976-02-03
• Bridged Bicyclic Cores Containing a 1,1-Diarylethylene Motif Are High-Affinity Subtype-Selective Ligands for the Estrogen Receptor
  作者：Rajeev S. Muthyala、Shubin Sheng、Kathryn E. Carlson、Benita S. Katzenellenbogen、John. A. Katzenellenbogen

  DOI：10.1021/jm0204800

  日期：2003.4.1

  The actions of estrogens are mediated through the two estrogen receptors, ERalpha and ERbeta. Compounds that interact selectively with ERalpha or ERbeta are of interest because they could be used to explore the biological roles of these ER subtypes and they might be interesting estrogen pharmaceuticals. In a new approach to develop ER subtype-selective ligands, we have embellished the 1,1-diarylethylene motif, common to many nonsteroidal estrogens, with various bridged bicyclic or tricyclic cores, including ones based on bicyclo [3.3.1] nonane, bicyclo [2.2.1] heptane, and selected bi- and tricyclic terpenoids. This design leads to three-dimensional ER ligands of unusual structure that we have used to probe the size and shape of the ligand binding pocket of ERalpha and ERbeta. Many of these compounds have high binding affinities, with the best having a bicyclo[3.3.1]nonane core and binding 3-5 times better than estradiol to both ER subtypes. Some of the compounds show significant affinity selectivity in favor of ERbeta (4- to 5-fold), and in cell-based assays for transcriptional activity most are partial agonists on ERalpha and full antagonists on ERbeta.