2-phenyl-1-tosyloxy-2-propanol | 93006-85-0

• 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: 2-phenyl-1-tosyloxy-2-propanol
• 英文别名: 2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate；(2-hydroxy-2-phenylpropyl) 4-methylbenzenesulfonate
• CAS: 93006-85-0
• 化学式: C₁₆H₁₈O₄S
• 分子量: 306.383
• InChiKey: KPLGJNCVAVQNJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 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：

  2-phenyl-1-tosyloxy-2-propanol 、 6-乙氧基-2,2,4-三甲基-1,2-二氢喹啉 在 碳酸氢钠 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以66%的产率得到(2R,6R,11R)-3-(2-hydroxy-2-phenylpropyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocin-8-ol
  参考文献：
  名称：

  Development of novel LP1-based analogues with enhanced delta opioid receptor profile

  摘要：

  Pain relief achieved by co-administration of drugs acting at different targets is more effective than that obtained with conventional MOR selective agonists usually associated to relevant side effects. It has been demonstrated that simultaneously targeting different opioid receptors is a more effective therapeutic strategy. Giving the promising role for DOR in pain management, novel LP1-based analogues with different N-substituents were designed and synthesized with the aim to improve DOR profile. For this purpose, we maintained the phenyl ring in the N-substituent of 6,7-benzomorphan scaffold linked to an ethyl spacer bearing a hydroxyl/methyl or methoxyl group at carbon 2 or including it in a 1,4-benzodioxane ring. LP1 analogues were tested by competition binding assays. Compounds 6 (K-i(MOR) = 2.47 nM, K-i(DOR) = 9.6 nM), 7 (K-i(DOR) = 0.5 nM and K-i(DOR) = 0.8 nM) and 9 (K-i(DOR) = 1.08 nM, K-i(DOR) = 6.6 nM) retained MOR affinity but displayed an improved DOR binding capacity as compared to LP1 (K-i(DOR) = 0.83 nM, KKiDOR = 29.1 nM). Moreover, GPI and MVD functional assays indicated that compounds 6 (IC50 = 49.2 and IC50 = 10.8 nM), 7 (IC50 = 9.9 and IC50 = 11.8 nM) and 9 (IC50 = 21.5 and IC50 = 4.4 nM) showed a MOR/DOR agonist profile, unlike LP1 that was a MOR agonist/DOR antagonist (IC50 = 1.9 and IC50 = 1240 nM). Measurements of their antinociceptive effect was evaluated by mice radiant tail flick test displaying for compounds 6, 7 and 9 ED50 values of 1.3, 1.0 and 0.9 mg/kg, i.p., respectively. Moreover, the antinociceptive effect of compound 9 was longer lasting with respect to LP1. In conclusion the N-substituent nature of compounds 6, 7 and 9 shifts the DOR profile of LP1 from antagonism to agonism. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.021
• 作为产物：
  描述：

  DL-阿卓乳酸半水物 在 吡啶 、 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 2.0h， 生成 2-phenyl-1-tosyloxy-2-propanol
  参考文献：
  名称：

  A concise synthesis of (S)-(+)-1-(4-{2-[bis-(4-fluorophenyl)methoxy]-ethyl}piperazin-1-yl)-2-phenylpropan-2-ol dimaleate

  摘要：

  (S)-(+)-1-(4-{2-[Bis-(4-fluorophenyl)methoxy]-ethyl}piperazin-1-yl)-2-phenylpropan-2-ol dimaleate was prepared in several steps from (S)-(+)-atrolactic acid by a process permitting synthesis of multigram quantities. With the information provided by asymmetric synthesis, the X-ray crystal structure was solved. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2003.05.001

文献信息

• [EN] INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1<br/>[FR] INHIBITEURS DE LA 11-BÊTA-HYDROXYSTÉROÏDE DÉSHYDROGÉNASE DE TYPE 1
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2009117109A1

  公开（公告）日：2009-09-24

  This invention relates to novel compounds of the Formula (I) and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11β-HSD1 in mammals.

  本发明涉及一种新型化合物的公式（I）及其药用盐，以及与之相关的药物组合物，用于治疗与哺乳动物中11β-HSD1的调节或抑制相关的疾病。
• Inhibitors Of 11beta-Hydroxysteroid Dehydrogenase Type 1
  申请人：Claremon David A.

  公开号：US20110105504A1

  公开（公告）日：2011-05-05

  This invention relates to novel compounds of the Formula (I) and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11β-HSD1 in mammals.

  本发明涉及公式(I)的新化合物及其药学上可接受的盐，以及这些化合物的药物组合物，用于治疗与哺乳动物中11β-HSD1的调节或抑制有关的疾病。
• Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols:  Scope and Mechanistic Insight
  作者：Michael J. Martinelli、Rajappa Vaidyanathan、Joseph M. Pawlak、Naresh K. Nayyar、Ulhas P. Dhokte、Christopher W. Doecke、Lisa M. H. Zollars、Eric D. Moher、Vien Van Khau、Berta Košmrlj

  DOI：10.1021/ja016031r

  日期：2002.4.1

  This paper describes a convenient protocol for the regioselective sulfonylation of alpha-chelatable alcohols. Typically, the reaction of alpha-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of Sn-119 NMR studies.
• Dibutyltin Oxide Catalyzed Selective Sulfonylation of α-Chelatable Primary Alcohols
  作者：Michael J. Martinelli、Naresh K. Nayyar、Eric D. Moher、Ulhas P. Dhokte、Joseph M. Pawlak、Rajappa Vaidyanathan

  DOI：10.1021/ol990658l

  日期：1999.8.1

  The reaction of substituted glycols with catalytic dibutyltin oxide, stoichiometric p-toluenesulfonyl chloride, and triethylamine in CH2Cl2 resulted in the complete and rapid sulfonylation at the primary alcohol, The alpha-heterosubstituted primary alcohol moiety appeared optimal for best results, supporting the intermediacy of a five-membered chelate, The role of the amine is discussed, in addition to catalyst requirements and solvent effects.
• Selective sulfonylation of 1,2-diols and derivatives catalyzed by a recoverable fluorous tin oxide
  作者：Brian Bucher、Dennis P Curran

  DOI：10.1016/s0040-4039(00)01720-2

  日期：2000.12

  Fluorous tin oxide (C6F13CH2CH2)(2)SnO is readily synthesized, exhibits spectra that are generally similar to dibutyltin oxide and appears to exist as an oligomer or polymer. The fluorous tin oxide can be used catalytically to effect the selective monotosylation of 1,2-diols with TsCl/Et3N, and it can be readily recovered and reused. (C) 2000 Published by Elsevier Science Ltd.