4-氯苯基丁基 4-甲基苯磺酸酯 | 93982-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯苯基丁基 4-甲基苯磺酸酯
• 中文别名: 4-氯苯基丁基4-甲基苯磺酸酯
• 英文名称: 4-(4-chlorophenyl)butyl tosylate
• 英文别名: 4-Chlorophenylbutyl 4-methylbenzenesulphonate；4-(4-chlorophenyl)butyl 4-methylbenzenesulfonate
• CAS: 93982-99-1
• 化学式: C₁₇H₁₉ClO₃S
• 分子量: 338.855
• InChiKey: GMBWFZODOYMUJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  4-氯苯基丁基 4-甲基苯磺酸酯 在 potassium tert-butylate 、 乙酸酐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.58h， 生成
  参考文献：
  名称：

  Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents

  摘要：

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.

  DOI：

  10.1021/jm00102a016
• 作为产物：
  描述：

  3-(4-氯苯甲酰)丙酸 在 吡啶 、 三氯化铝 、 硼烷-叔丁基胺 作用下， 以 二氯甲烷 为溶剂， 反应 219.5h， 生成 4-氯苯基丁基 4-甲基苯磺酸酯
  参考文献：
  名称：

  Synthesis of [18F]Fluoroclofilium as a potential cardiac imaging agent for PET studies

  摘要：

  N-4-(4-氯苯基)丁基-N,N-二乙基-7-[18F]氟庚基铵（[18F]-氟氯菲啶）已被制备为潜在的心脏成像剂。为了合成这种放射性标记的铵盐，其对甲苯磺酸酯化的类似物被制备为前体，而非放射性的氟类似物被合成作为参比化合物。通过在乙腈中使用Kryptofix-2.2.2的存在下，将N-4-(4-氯苯基)丁基-N,N-二乙基-7-(对甲苯磺酰氧基)庚基铵对甲苯磺酸盐与18F−反应，实现了放射性氟标记。版权所有 © 2003 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.747

文献信息

• Photoexcited Palladium-Initiated Remote Desaturation of <i>N</i>-Alkoxypyridinium Salts
  作者：Weiwei Jin、Shouyun Yu

  DOI：10.1021/acs.joc.2c02036

  日期：2022.11.4

  1,5-Hydrogen atom transfer (HAT) is an effective strategy to achieve remote desaturation of nonfunctionalized alkanes. Herein, we report a photoinduced remote desaturation reaction of N-alkoxypyridinium salts, which serve as alkoxyl radical precursors. Mechanistic studies show that a single electron transfer between the excited palladium complex and a N-alkoxypyridinium salt initiates a radical chain

  1,5-氢原子转移 (HAT) 是一种实现非功能化烷烃远程脱饱和的有效策略。在此，我们报告了作为烷氧基自由基前体的N -烷氧基吡啶盐的光诱导远程去饱和反应。机理研究表明，激发的钯络合物和N -烷氧基吡啶盐之间的单个电子转移会引发自由基链过程，导致N -烷氧基吡啶盐去饱和。这种链式机制得到了该反应 (Φ = 82) 量子产率测量的支持。该反应适用于一系列N -烷氧基吡啶盐，包括一些复杂的分子衍生盐。
• Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents
  作者：Jay Wrobel、Arlene Dietrich、Shiela A. Woolson、Jane Millen、Michael McCaleb、Maria C. Harrison、Thomas C. Hohman、Janet Sredy、Donald Sullivan

  DOI：10.1021/jm00102a016

  日期：1992.11

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.
• Synthesis of [18F]Fluoroclofilium as a potential cardiac imaging agent for PET studies
  作者：K. H. Yu、Y. S. Kim、S. W. Kim、J. H. Park、S. D. Yang、W. Herdering、A. Knoechel

  DOI：10.1002/jlcr.747

  日期：2003.10.31

  N-4-(4-chlorophenyl)butyl-N,N-diethyl-7-[18F]fluoroheptylammonium ([18F]-fluoroclofilium) has been prepared as a potential cardiac imaging agent. For the synthesis of this radiolabelled ammonium salt, its tosyloxylated analogue was prepared as a precursor, and the non-radioactive fluorine analogue was synthesized as a reference compound. Radiofluorination was achieved by the treatment of N-4-(4-chlorophenyl)butyl-N,N-diethyl-7-(p-toluenesulfonyloxy)heptylammonium p-toluenesulfonate with 18F− in the presence of Kryptofix-2.2.2 in acetonitrile. Copyright © 2003 John Wiley & Sons, Ltd.

  N-4-(4-氯苯基)丁基-N,N-二乙基-7-[18F]氟庚基铵（[18F]-氟氯菲啶）已被制备为潜在的心脏成像剂。为了合成这种放射性标记的铵盐，其对甲苯磺酸酯化的类似物被制备为前体，而非放射性的氟类似物被合成作为参比化合物。通过在乙腈中使用Kryptofix-2.2.2的存在下，将N-4-(4-氯苯基)丁基-N,N-二乙基-7-(对甲苯磺酰氧基)庚基铵对甲苯磺酸盐与18F−反应，实现了放射性氟标记。版权所有 © 2003 John Wiley & Sons, Ltd.