3-(2-hydroxyphenyl)-1-propyl tosylate | 81246-46-0

• 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-(2-hydroxyphenyl)-1-propyl tosylate
• 英文别名: 3-(o-hydroxyphenyl)-1-tosyloxypropane；3-(2-hydroxyphenyl)propyl 4-methylbenzenesulfonate
• CAS: 81246-46-0
• 化学式: C₁₆H₁₈O₄S
• 分子量: 306.383
• InChiKey: JHOMRHDJGYJZRO-UHFFFAOYSA-N

物化性质

• 沸点：
  487.3±33.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxyphenyl)-1-propyl tosylate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 19.0h， 以51%的产率得到2-(3-azidopropyl)phenol
  参考文献：
  名称：

  用同价二价双位配体探测β2-肾上腺素能受体亚稳结合位点的存在。

  摘要：

  在本文中，我们报道了针对同一受体单元内正构结合位点（OBS）和亚稳结合位点（MBS）的双配位配体的开发。先前对配体与β2-肾上腺素受体（β2AR）结合的分子动力学研究表明，配体在瞬时的，保守性较低的MBSs处暂停。我们设想，MBS可以被视为变构结合位点，并由连接两个相同药效基团的同双价双位配体靶向。基于拮抗剂（S）-普萘洛尔对接至OBS和MBS中来设计此类配体并进行合成。药理学特征显示，与（S）-阿普萘洛尔相比，配体具有相似的效价和亲和力，β2/β1AR选择性略有增加，和/或β2AR的离解速率大大降低。截短的双位配体表明亚稳态药效团的主要贡献是与β2AR的疏水相互作用，而单独的接头降低了正构片段的效力。总而言之，该研究强调了靶向MBS改善配体药理作用的潜力。

  DOI：

  10.1021/acs.jmedchem.9b00595
• 作为产物：
  描述：

  氢化肉桂酸内酯 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 3-(2-hydroxyphenyl)-1-propyl tosylate
  参考文献：
  名称：

  用同价二价双位配体探测β2-肾上腺素能受体亚稳结合位点的存在。

  摘要：

  在本文中，我们报道了针对同一受体单元内正构结合位点（OBS）和亚稳结合位点（MBS）的双配位配体的开发。先前对配体与β2-肾上腺素受体（β2AR）结合的分子动力学研究表明，配体在瞬时的，保守性较低的MBSs处暂停。我们设想，MBS可以被视为变构结合位点，并由连接两个相同药效基团的同双价双位配体靶向。基于拮抗剂（S）-普萘洛尔对接至OBS和MBS中来设计此类配体并进行合成。药理学特征显示，与（S）-阿普萘洛尔相比，配体具有相似的效价和亲和力，β2/β1AR选择性略有增加，和/或β2AR的离解速率大大降低。截短的双位配体表明亚稳态药效团的主要贡献是与β2AR的疏水相互作用，而单独的接头降低了正构片段的效力。总而言之，该研究强调了靶向MBS改善配体药理作用的潜力。

  DOI：

  10.1021/acs.jmedchem.9b00595

文献信息

• Certain benzoxepins and their pharmaceutical compositions and methods
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04859683A1

  公开（公告）日：1989-08-22

  Certain specific substituted 9-N-(1-azabicyclo[3.3.1.]nonan-4-yl)carboxamido-2,3,4,5-tetrahydro-1-benzo xepins and their valuable use as 5-HT.sub.3 antagonists having CNS and gastric prokinetic activity and void of any significant D.sub.2 receptor binding properties are disclosed. Methods for their preparation also are described.

  本文披露了特定的特定的替代9-N-(1-azabicyclo[3.3.1.]nonan-4-yl)carboxamido-2,3,4,5-四氢-1-苯并二氧杂环庚烷以及它们作为5-HT.sub.3拮抗剂的有价值的用途，具有中枢神经系统和胃动力活性，并且不具有任何显著的D.sub.2受体结合特性。同时也描述了它们的制备方法。
• Quinuclidyl benzoxepins as 5-HT.sub.3 antagonists
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04857517A1

  公开（公告）日：1989-08-15

  Certain specific substituted 9-N-(1-azabicyclo-[2.2.2.]octan-3-yl)carboxamido-2,3,4,5-tetrahydro-1-benz oxepins and their valuable use as 5-HT.sub.3 antagonists having CNS and gastric prokinetic acticity and void of any significant D.sub.2 receptor binding properties are disclosed. Methods for their preparation also are described.

  本发明揭示了某些特定的替代的9-N-(1-azabicyclo-[2.2.2.]辛烷-3-基)羧胺基-2,3,4,5-四氢-1-苯并噁啉及其作为5-HT.sub.3拮抗剂的有价值用途，具有中枢神经系统和胃动力促进作用，且不具有任何显著的D.sub.2受体结合性质。同时还描述了它们的制备方法。
• Benzoxepins as intermediates to 5HT.sub.3 antagonists
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04924010A1

  公开（公告）日：1990-05-08

  Certain specific substituted 9-N-(1-azabicycolo-[2.2.2.]octan-3-yl)carboxamido-2,3,4,5-tetrahydro-1-ben zoxepins and their valuable use as 5-HT.sub.3 antagonists having CNS and gastric prokinetic activity and void of any significant D.sub.2 receptor binding properties are disclosed. Methods for their preparation also are described.

  本发明涉及特定的取代9-N-(1-氮杂双环[2.2.2]辛烷-3-基)羧酰胺基-2,3,4,5-四氢-1-苯并氧杂芳烃及其作为5-HT.sub.3拮抗剂的有价值的应用，具有中枢神经系统和胃动力学活性，并且不具有任何显著的D.sub.2受体结合性质。同时还描述了制备它们的方法。
• Stable Isotope Characterization of the <i>ortho</i>-Oxygenated Phenylpropanoids:  Coumarin and Melilotol
  作者：Elisabetta Brenna、Giovanni Fronza、Claudio Fuganti、Francesco G. Gatti、Valentina Grande、Stefano Serra、Claude Guillou、Fabiano Reniero、Francesca Serra

  DOI：10.1021/jf0518507

  日期：2005.11.1

  The natural abundance H-2 NMR spectra of extractive coumarin 10 and of its dihydroderivative melilotol 11 produced by baker's yeast reduction has been compared with synthetic materials. Diagnostic for the differentiation of 10 are the (D/H)(beta) values, which are in the 128.1 -133.6 ppm interval for the natural compounds but 258.5 and 189.8 ppm for the synthetic materials. Such a dramatic difference is also found for methyl cinnamate 12, which shows (D/H)(beta) values of 127.2 and 515.8 ppm, respectively. In extractive 10, the ratio (D/H)(4(Para))/(D/H)(6(ortho)) = 1.24 is similar to that observed in structurally related salicin and methyl salicylate. Coumarin 10 is transformed in salicyl alcohol 9, providing diacetate 14, showing in the natural series the trend (D/H)(3(meta)) > (D/H)(4(para)) > (D/H)(5(meta)) similar to (D/H)(6(ortho)). A similar trend is shown also by the synthetic 10. A clear distinction between extractive and synthetic 10 is obtained through 6180 determinations on 10 and on chroman 13. The bulk delta O-18 values in the extractive series of 10 are 20.3, 23.6, and 22.6 parts per thousand, while those of the aromatic oxygen are 2.3, 0.5, and -0.5 parts per thousand. In the synthetic sample, the values are 12.6 and 5.6%., respectively. As a final product, the reduction of 10 leads to the dihydroderivative 11. Both the baker's yeast reduction and the catalytic hydrogenation lead to a marked decrease of the deuterium content of 11, which is stronger for the beta-position than for the alpha-position.
• Methylase models: studies on general-base vs. nucleophilic catalysis in the intramolecular alkylation of phenols
  作者：Jay O. Knipe、Peter J. Vasquez、James K. Coward

  DOI：10.1021/ja00375a045

  日期：1982.6