(S)-1-(4-methoxyphenyl)butan-2-ol | 179396-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-1-(4-methoxyphenyl)butan-2-ol
• 英文别名: (2S)-1-(4-methoxyphenyl)butan-2-ol
• CAS: 179396-74-8
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: ARRSWKWGQREELC-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-methoxyphenyl)butan-2-ol 在 sodium azide 、 palladium 10% on activated carbon 、 palladium on activated charcoal 、 氢气 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -70.0~120.0 ℃ 、344.75 kPa 条件下， 反应 84.0h， 生成 (R,R')-(-)-5-(1-hydroxy-2-((1-(4-methoxyphenyl)butan-2-yl)amino)ethyl)benzene-1,3-diol
  参考文献：
  名称：

  Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor

  摘要：

  The beta(2)-adrenergic receptor (beta(2)-AR) agonist [H-3]-(R,R')-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (K-i values) of the stereoisomers of a series of 4'-methoxyfenoterol analogs in which the length of the alkyl substituent at alpha' position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [H-3]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the beta(2)-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the alpha' position. The results also indicate that the K-i values obtained using [H-3]-(R,R')methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [H-3]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the beta(2)-AR conformation probed by [H-3]-(R,R')-4'-methoxyfenoterol. The CoMFA model of the agonist-stabilized beta(2)-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the beta(2)-AR is governed to a greater extend by steric effects than binding to the [H-3]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.030
• 作为产物：
  描述：

  (S)-(-)-1,2-环氧丁烷 、 4-碘苯甲醚 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.83h， 以72%的产率得到(S)-1-(4-methoxyphenyl)butan-2-ol
  参考文献：
  名称：

  Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor

  摘要：

  The beta(2)-adrenergic receptor (beta(2)-AR) agonist [H-3]-(R,R')-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (K-i values) of the stereoisomers of a series of 4'-methoxyfenoterol analogs in which the length of the alkyl substituent at alpha' position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [H-3]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the beta(2)-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the alpha' position. The results also indicate that the K-i values obtained using [H-3]-(R,R')methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [H-3]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the beta(2)-AR conformation probed by [H-3]-(R,R')-4'-methoxyfenoterol. The CoMFA model of the agonist-stabilized beta(2)-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the beta(2)-AR is governed to a greater extend by steric effects than binding to the [H-3]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.030

文献信息

• DDQ mediated stereoselective intermolecular benzylic CN bond formation: Synthesis of (−)-cytoxazone, (−)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity
  作者：Macha Lingamurthy、Gopalal Rao Nalliboina、Maddimsetti Venkateswara Rao、Batchu Venkateswara Rao、Bonam Srinivasa Reddy、Halmuthur Mahabalarao Sampath Kumar

  DOI：10.1016/j.tet.2017.01.059

  日期：2017.3

  strategy for the synthesis of (−)-cytoxazone, (−)-4-epi-cyoxazone and their analogues by using DDQ mediated diastereoselective intermolecular benzylic amination has been described. Immunological evaluation of their cytokine modulating activity revealed that the change of hydroxy methyl to methyl group increased the cellular immunity in in-vitro cultures. Changes in the stereochemistry of oxazolidine

  已描述了使用DDQ介导的非对映选择性分子间苄基胺化合成（-）-cytoxazone，（-）-4- Epi- cyoxazone及其类似物的简便有效策略。对它们的细胞因子调节活性的免疫学评估表明，羟甲基甲基的变化增加了体外培养物中的细胞免疫性。恶唑烷的立体化学变化并未影响其生物学活性。
• Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor
  作者：Anita Plazinska、Karolina Pajak、Ewelina Rutkowska、Lucita Jimenez、Joseph Kozocas、Gary Koolpe、Mary Tanga、Lawrence Toll、Irving W. Wainer、Krzysztof Jozwiak

  DOI：10.1016/j.bmc.2013.11.030

  日期：2014.1

  The beta(2)-adrenergic receptor (beta(2)-AR) agonist [H-3]-(R,R')-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (K-i values) of the stereoisomers of a series of 4'-methoxyfenoterol analogs in which the length of the alkyl substituent at alpha' position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [H-3]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the beta(2)-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the alpha' position. The results also indicate that the K-i values obtained using [H-3]-(R,R')methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [H-3]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the beta(2)-AR conformation probed by [H-3]-(R,R')-4'-methoxyfenoterol. The CoMFA model of the agonist-stabilized beta(2)-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the beta(2)-AR is governed to a greater extend by steric effects than binding to the [H-3]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role. (C) 2013 Elsevier Ltd. All rights reserved.