4-(4-methylenecyclohexyl)phenol | 1438738-02-3

• 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-methylenecyclohexyl)phenol
• 英文别名: 4-(4-hydroxyphenyl)(methylene)cyclohexane；(4-hydroxyphenyl)-4-methylenecyclohexane；ISP365；4-(4-Methylidenecyclohexyl)phenol
• CAS: 1438738-02-3
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: YGKNWJASJUQVMN-UHFFFAOYSA-N

物化性质

• 沸点：
  313.9±41.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(4-methylenecyclohexyl)phenol 在 吡啶 、 过氧乙酸 、 Mo(acac)2 、 camphor-10-sulfonic acid 、 水 、 双氧水 、 sodium acetate 、 四丁基硫酸氢铵 、 magnesium sulfate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Comparative Antimalarial Activities and ADME Profiles of Ozonides (1,2,4-trioxolanes) OZ277, OZ439, and Their 1,2-Dioxolane, 1,2,4-Trioxane, and 1,2,4,5-Tetraoxane Isosteres

  摘要：

  To ascertain the structure-activity relationship of the core 1,2,4-trioxolane substructure of dispiro ozonides OZ277 and OZ439, we compared the antimalarial activities and ADME profiles of the 1,2-dioxolane, 1,2,4-trioxane, and 1,2,4,5-tetraoxane isosteres. Consistent with previous data, both dioxolanes had very weak antimalarial properties. For the OZ277 series, the trioxane isostere had the best ADME profile, but its overall antimalarial efficacy was not superior to that of the trioxolane or tetraoxane isosteres. For the OZ439 series, there was a good correlation between the antimalarial efficacy and ADME profiles in the rank order trioxolane > trioxane > tetraoxane. As we have previously observed for OZ439 versus OZ277, the OZ439 series peroxides had superior exposure and efficacy in mice compared to the corresponding OZ277 series peroxides.

  DOI：

  10.1021/jm400004u
• 作为产物：
  描述：

  4-(4-t-butyldimethylsilyloxyphenyl)cyclohexan-1-one 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 生成 4-(4-methylenecyclohexyl)phenol
  参考文献：
  名称：

  AC雌激素作为有效的选择性雌激素受体-β激动剂（SERBA），可增强低雌激素条件下的记忆巩固。

  摘要：

  雌激素受体-β（ERβ）是绝经后女性记忆巩固的药物靶点。本文报道了一系列具有体内功效的有效和选择性的ERβ激动剂（SERBA），它们是AC雌激素，缺乏B和D雌激素环。相对于其他七个核激素受体，最有力和选择性的AC雌激素对激活ER具有选择性，在基于细胞和直接结合的测定中，β的选择性比α亚型高出惊人的750倍，EC50为20-30 nM。在不同测定中对效力的比较表明，ER同工型的选择性与化合物驱动激活转录所需的生产性构象变化的能力有关。该化合物在微注入背侧海马后和腹膜内注射后也显示出体内功效（0。5 mg / kg）或口服管饲（0.5 mg / kg）。这种简单而新颖的AC雌激素具有选择性，可渗透大脑，并有助于记忆巩固。

  DOI：

  10.1021/acs.jmedchem.7b01601

文献信息

• [EN] SUBSTITUTED (4'-HYDROXYPHENYL)CYCLOALKANE AND (4'-HYDROXYPHENYL)CYCLOALKENE COMPOUNDS AND USES THEREOF AS SELECTIVE AGONISTS OF THE ESTROGEN RECEPTOR BETA ISOFORM FOR ENHANCED MEMORY CONSOLIDATION<br/>[FR] COMPOSÉS (4'-HYDROXYPHÉNYL)CYCLOALCANE ET (4'-HYDROXYPHÉNYL)CYCLOALCÈNE SUBSTITUÉS ET LEURS UTILISATIONS EN TANT QU'AGONISTES SÉLECTIFS DE L'ISOFORME BÊTA DU RÉCEPTEUR DES ŒSTROGÈNES POUR UNE CONSOLIDATION AMÉLIORÉE DE MÉMOIRE
  申请人：UNIV MARQUETTE

  公开号：WO2018183800A1

  公开（公告）日：2018-10-04

  Disclosed are substituted (4'-hydroxylphenyl)cycloalkane compounds and substituted (4'-hydroxylphenyl)cycloalkene compounds and there use as selective agonists of the estrogen receptor beta isoform (ERβ). The disclosed compounds may be formulated as pharmaceutical compositions and administered for treating diseases associated with ER activity, such as neurological, psychiatric, and/or cell proliferative diseases and disorders as well as for enhancing memory consolidation in subjects in need thereof.

  本文披露了替代的（4'-羟基苯基）环烷烃化合物和替代的（4'-羟基苯基）环烯烃化合物以及它们作为雌激素受体β异构体（ERβ）的选择性激动剂的用途。所披露的化合物可制成药物组合物，并用于治疗与ER活性相关的疾病，如神经学、精神病学和/或细胞增殖性疾病和障碍，以及用于增强需要的受试者的记忆巩固。
• Modular access to substituted cyclohexanes with kinetic stereocontrol
  作者：Yangyang Li、Yuqiang Li、Hongjin Shi、Hong Wei、Haoyang Li、Ignacio Funes-Ardoiz、Guoyin Yin

  DOI：10.1126/science.abn9124

  日期：2022.5.13

  biologically active compounds. Although methods for the synthesis of thermodynamically favored, disubstituted cyclohexanes are well established, a reliable and modular protocol for the synthesis of their stereoisomers is still elusive. Herein, we report a general strategy for the modular synthesis of disubstituted cyclohexanes with excellent kinetic stereocontrol from readily accessible substituted methylenecyclohexanes

  取代的六元环烃是生物活性化合物的常见成分。尽管合成热力学有利的二取代环己烷的方法已经很成熟，但合成其立体异构体的可靠和模块化方案仍然难以捉摸。在此，我们报告了通过实施链行走催化从易于获得的取代亚甲基环己烷模块化合成具有优异动力学立体控制的二取代环己烷的一般策略。从机制上讲，最初引入与环己烷相邻的空间要求高的硼酯基团是指导立体化学结果的关键。
• Substituted (4'-hydroxyphenyl)cyclohexane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform
  申请人：Marquette University

  公开号：US10570077B2

  公开（公告）日：2020-02-25

  Disclosed are substituted (4′-hydroxylphenyl)cycloalkane compounds and there use as selective agonists of the estrogen receptor beta isoform (ERβ). The disclosed compounds may be formulated as pharmaceutical compositions and administered to treat diseases associated with ER activity, such as proliferative diseases and disorders and/or psychiatric diseases or disorders.

  公开了取代的（4′-羟基苯基）环烷烃化合物及其作为雌激素受体β异构体（ERβ）选择性激动剂的用途。所公开的化合物可配制成药物组合物，用于治疗与ER活性相关的疾病，如增殖性疾病和紊乱和/或精神疾病或紊乱。
• SUBSTITUTED (4'-HYDROXYPHENYL)CYCLOAKLKANE COMPOUNDS AND USES THEREOF AS SELECTIVE AGONISTS OF THE ESTROGEN RECEPTOR BETA ISOFORM
  申请人：Marquette University

  公开号：US20160340279A1

  公开（公告）日：2016-11-24

  Disclosed are substituted (4′-hydroxylphenyl)cycloalkane compounds and there use as selective agonists of the estrogen receptor beta isoform (ERβ). The disclosed compounds may be formulated as pharmaceutical compositions and administered to treat diseases associated with ER activity, such as proliferative diseases and disorders and/or psychiatric diseases or disorders.
• Substituted (4-Hydroxyphenyl)Cycloalkane and (4-Hydroxyphenyl)Cycloalkene Compounds and Uses Thereof as Selective Agonists of the Estrogen Receptor Beta Isoform for Enhanced Memory Consolidation
  申请人：Marquette University

  公开号：US20210340155A1

  公开（公告）日：2021-11-04

  Disclosed are substituted (4′-hydroxylphenyl)cycloalkane compounds and substituted (4′-hydroxylphenyl)cycloalkene compounds and there use as selective agonists of the estrogen receptor beta isoform (ERβ). The disclosed compounds may be formulated as pharmaceutical compositions and administered for treating diseases associated with ER activity, such as neurological, psychiatric, and/or cell proliferative diseases and disorders as well as for enhancing memory consolidation in subjects in need thereof.