1-(4'-nitrophenoxy)-3-phenoxypropan-2-ol | 94925-78-7

• 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: 1-(4'-nitrophenoxy)-3-phenoxypropan-2-ol
• 英文别名: 1-(4-nitrophenoxy)-3-phenoxypropan-2-ol；1-(4-nitro-phenoxy)-3-phenoxy-propan-2-ol
• CAS: 94925-78-7
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: KYJCOORUDUPNLT-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  486.5±30.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4'-nitrophenoxy)-3-phenoxypropan-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 1-(4-Aminophenoxy)-3-phenoxypropan-2-ol
  参考文献：
  名称：

  Synthesis and Antiallergic Activity of Dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-Toluenesulfonate Derivatives

  摘要：

  The derivatives of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonates were synthesized and evaluated for antiallergic activity. The 2,3-dihydroxyethoxy group was introduced to the phenyl ring from the standpoint of lipophilicity and electronic effects of substituent. The IgE-induced rat passive cutaneous anaphylaxis (PCA) was inhibited by oral administration of several substituted 2-[(4-propoxyphenyl)carbamoyl]ethyldimethylsulfonium p-toluenesulfonate derivatives. Among them (+/-)-2-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-carbamoyl]ethyldimethylsulfonium p-toluenesulfonate (1a, IPD-1151T) was found to possess considerable activity in the PCA test, and it was launched as Suplatast tosilate in Japan.

  DOI：

  10.1021/jm970285z
• 作为产物：
  描述：

  对硝基苯酚 、 苯基缩水甘油醚 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到1-(4'-nitrophenoxy)-3-phenoxypropan-2-ol
  参考文献：
  名称：

  Bi(OTf)3 催化的环氧化物与酚的区域选择性开环：1,3-二芳氧基-2-丙醇的简易合成

  摘要：

  在催化量的三氟甲磺酸铋 (III) 存在下，取代的芳基环氧乙烷与酚类轻松开环，在温和条件下以优异的产率得到 1,3-二芳氧基-2-丙醇。三氟甲磺酸铋 (III) 相对无毒、易于处理且价格低廉，这使得该程序对大规模合成特别有吸引力。

  DOI：

  10.1246/cl.2005.1142

文献信息

• Synergistic dual activation catalysis by palladium nanoparticles for epoxide ring opening with phenols
  作者：Kapileswar Seth、Sudipta Raha Roy、Bhavin V. Pipaliya、Asit K. Chakraborti

  DOI：10.1039/c3cc42507j

  日期：——

  Synergistic dual activation catalysis has been devised for epoxide phenolysis wherein palladium nanoparticles induce electrophilic activation via coordination with the epoxide oxygen followed by nucleophilic activation through anion-pi interaction with the aromatic ring of the phenol, and water (reaction medium) also renders assistance through 'epoxide-phenol' dual activation.

  已经设计了用于环氧酚醛化的协同双重活化催化，其中钯纳米颗粒通过与环氧氧的配位而诱导亲电活化，然后通过与苯酚的芳香环的阴离子-π相互作用进行亲核活化，并且水（反应介质）也通过“环氧-苯酚的双重活化。
• 2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2- diazaphosphorine Supported on Polystyrene (PS-BEMP) as an Efficient Recoverable and Reusable Catalyst for the Phenolysis of Epoxides under Solvent-Free Conditions
  作者：Artis Zvagulis、Simona Bonollo、Daniela Lanari、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1002/adsc.201000375

  日期：2010.10.4

  setting a cyclic continuous-flow reactor operating under solvent-free conditions (SolFC) that allowed us to minimize waste and reduce the E-factor by 95% compared to batch conditions. In addition the representative synthesis of a 2,3-dihydrobenzo[1,4]dioxepin-5-one has been realized. Optimization of this process was achieved by setting up an automated multi-step continuous-flow reactor based on a phenolysis

  2叔聚苯乙烯（PS-BEMP）上负载的-Butylimino-2-二乙氨基-1,3-二甲基过氢-1,3,2-二氮杂膦是一种有效的催化剂，用于使环氧化物与酚（1.0当量）开环。已经获得了优异的产率，并且在大多数情况下，最终产物已经以纯净的形式分离出来，而无需任何额外的纯化步骤。与该协议相关的E因子很小，并且通过设置在无溶剂条件下运行的循环连续流反应器（SolFC）获得了进一步的改进，这使我们能够最大限度地减少浪费并将E因子与批处理条件相比减少了95％ 。另外，已经实现了2，3-二氢苯并[1，4]二氧杂环戊烯-5-酮的代表性合成。通过建立基于酚醛化方法的自动化多步连续流反应器并随后通过反应混合物的热处理进行内酯化来实现此过程的优化。3-Phenoxymethyl-2,3-dihydrobenzo [e [[1,4] dioxepin-5-one）以纯克形式和多克级分离，总收率非常令人满意，为86％，E因子为1
• Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases
  作者：Marco Tassi、Elena Bartollini、Peter Adriaensens、Luca Bianchi、Balaka Barkakaty、Robert Carleer、Jihua Chen、Dale K. Hensley、Assunta Marrocchi、Luigi Vaccaro

  DOI：10.1039/c5ra21140a

  日期：——

  In view of searching for efficient solid catalysts to be used in environmentally friendly reaction conditions, novel gel-type cross-linked polystyrenes functionalized with diethylamine and 1,5,7-triazabicyclo[4.4.0]dec-5-ene, have been prepared.

  鉴于寻找在环保反应条件下使用的高效固体催化剂，已制备了新型的明胶型交联聚苯乙烯，它们经过二乙胺和1,5,7-三氮杂双环[4.4.0]癸-5-烯功能化。
• Levas, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1946, vol. 223, p. 901
  作者：Levas

  DOI：——

  日期：——
• Synthesis and Antiallergic Activity of Dimethyl-2-(phenylcarbamoyl)ethylsulfonium <i>p</i>-Toluenesulfonate Derivatives
  作者：Yukio Tada、Ichiro Yamawaki、Shuichi Ueda、Hiroshi Matsumoto、Naosuke Matsuura、Mitsugi Yasumoto、Akihide Koda、Mikio Hori

  DOI：10.1021/jm970285z

  日期：1998.8.1

  The derivatives of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonates were synthesized and evaluated for antiallergic activity. The 2,3-dihydroxyethoxy group was introduced to the phenyl ring from the standpoint of lipophilicity and electronic effects of substituent. The IgE-induced rat passive cutaneous anaphylaxis (PCA) was inhibited by oral administration of several substituted 2-[(4-propoxyphenyl)carbamoyl]ethyldimethylsulfonium p-toluenesulfonate derivatives. Among them (+/-)-2-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-carbamoyl]ethyldimethylsulfonium p-toluenesulfonate (1a, IPD-1151T) was found to possess considerable activity in the PCA test, and it was launched as Suplatast tosilate in Japan.