1-methoxy-3-(4-nitrophenoxy)propan-2-ol | 94925-70-9

• 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-methoxy-3-(4-nitrophenoxy)propan-2-ol
• CAS: 94925-70-9
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: NEXKZJYBKGHMMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-methoxy-3-(4-nitrophenoxy)propan-2-ol 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 130.0h， 生成 2-{4-(2-hydroxy-3-methoxypropoxy)phenylcarbamoyl}ethyldimethylsulfonium p-toluenesulfonate
  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：

  (甲氧基甲基)环氧乙烷 、 对硝基苯酚 在 吡啶 作用下， 反应 6.0h， 生成 1-methoxy-3-(4-nitrophenoxy)propan-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

文献信息

• Cellulose sulfate: An efficient heterogeneous catalyst for the ring-opening of epoxides with alcohols and anilines
  作者：Pooja Chaudhary、Deepa、Dhan Raj Meena、Mohd Jubair Aalam、Geeta Devi Yadav、Surendra Singh

  DOI：10.1080/00397911.2021.1910304

  日期：2021.6.18

  acts as a heterogeneous catalyst for the ring-opening of epoxides with alcohols or anilines and the Friedel-Crafts reaction between N-benzylindole and crotonaldehyde at room temperature. Methanolysis of cyclic epoxides, styrene oxide, terminal aliphatic epoxides, and glycidyl ethers were carried out using the catalyst (0.4–6.8 mg/mmol of epoxide) and afforded the corresponding products in 53–97% isolated

  摘要 硫酸纤维素是通过将α-纤维素与浓硫酸在-10°C的乙醇中酯化而合成的。纤维素主要在纤维素的3、6和3、6位硫酸化。它在室温下用作环氧化物与醇或苯胺开环以及N-苄基吲哚和巴豆醛之间的Friedel-Crafts反应的非均相催化剂。使用催化剂（0.4–6.8 mg / mmol环氧）对环状环氧化合物，氧化苯乙烯，末端脂肪族环氧化合物和缩水甘油醚进行甲醇分解，在10分钟至24小时后，分离出的产率为53–97％，得到了相应的产物。硫酸纤维素已成功回收，并最多可重复使用3个催化循环，以使氧化苯乙烯与甲醇一起开环。
• Ring opening of epoxides with alcohols using Fe(Cp)2BF4 as catalyst
  作者：Geeta Devi Yadav、Surendra Singh

  DOI：10.1016/j.tetlet.2014.05.017

  日期：2014.7

  Fe(Cp)(2)BF4 is an efficient catalyst for the alcoholysis of aromatic, aliphatic, and cyclic epoxides giving excellent yields of the corresponding beta-alkoxy alcohols under ambient conditions. The methanolysis of styrene oxide using Fe(Cp)(2)BF4 as a catalyst (5 mol %) gave excellent yield of 2-methoxy-2-phenylethanol with complete regio-selectivity. The ring opening of cyclic epoxides gave 77-97% yields of trans-beta-methoxy alcohols, in 0.5-6 h. The use of 1,2-epoxyhexane and 1,2-epoxydodecane as substrates gave both regioisomers in excellent yields. The first order rate of reaction with respect to catalyst was observed for the kinetics of ring opening of 1,2-epoxyhexane with methanol. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.