5-乙基-2-吡啶乙醇对甲苯磺酸盐 | 144809-27-8

• 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: 5-乙基-2-吡啶乙醇对甲苯磺酸盐
• 英文名称: toluene-4-sulfonic acid 2-(5-ethylpyridin-2-yl)ethyl ester
• 英文别名: toluene-4-sulfonic acid-2-(5-ethylpyridin-2-yl)-ethyl ester；2-(5-ethylpyridin-2-yl)ethyl 4-methylbenzenesulfonate；2-(5-ethyl-pyridin-2-yl)ethyl p-toluenesulfonate；2-(5-ethyl-2-pyridyl)ethyl p-toluenesulfonate；5-Ethyl-2-pyridineethanol Tosylate
• CAS: 144809-27-8
• 化学式: C₁₆H₁₉NO₃S
• 分子量: 305.398
• InChiKey: XOKOJAMQAAPMRF-UHFFFAOYSA-N

物化性质

• 沸点：
  464.4±33.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、二氯甲烷、乙酸乙酯（微溶）、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-乙基-2-吡啶乙醇对甲苯磺酸盐 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 5-乙基-2-乙烯基吡啶
  参考文献：
  名称：

  Development of an Improved and Scalable Process for 2-(5-Ethylpyridin-2-yl)ethan-1-ol: Solvent-Free Reaction and Recycling of the Starting Material 5-Ethyl-2-picoline

  摘要：

  The main objective of this exercise was to develop a more efficient process for 2-(5-ethylpyridin-2-yl)ethan-1-ol (1), which is the key intermediate in the synthesis of pioglitazone hydrochloride. This process not only features the yield improvement of (1) by optimizing reaction variables in solvent-free conditions but also highlights improving the mass efficiency of 5-ethyl-2-picoline (2), thereby reducing the effluent load per kilogram of the intermediate.

  DOI：

  10.1021/op400196y
• 作为产物：
  描述：

  5-乙基-2-甲基-吡啶 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 水 、 甲苯 为溶剂， 155.0 ℃ 、600.01 kPa 条件下， 反应 4.0h， 生成 5-乙基-2-吡啶乙醇对甲苯磺酸盐
  参考文献：
  名称：

  Development of an Improved and Scalable Process for 2-(5-Ethylpyridin-2-yl)ethan-1-ol: Solvent-Free Reaction and Recycling of the Starting Material 5-Ethyl-2-picoline

  摘要：

  The main objective of this exercise was to develop a more efficient process for 2-(5-ethylpyridin-2-yl)ethan-1-ol (1), which is the key intermediate in the synthesis of pioglitazone hydrochloride. This process not only features the yield improvement of (1) by optimizing reaction variables in solvent-free conditions but also highlights improving the mass efficiency of 5-ethyl-2-picoline (2), thereby reducing the effluent load per kilogram of the intermediate.

  DOI：

  10.1021/op400196y

文献信息

• Phosphoryl Chloride Mediated Synthesis of 5-Arylidene-2,4-Thiazolidinediones Derivatives via Aromatic Bisulfite Adducts
  作者：Sandeep Mohanty、Sandeep G、Arun Karmakar

  DOI：10.2174/15701786113106660081

  日期：2014.2

  The carbon-carbon bond formation by the condensation of bisulfite adduct of aromatic aldehydes with thiazolidine-2, 4-dione to furnish 5-arylidene-2,4-thiazolidinedione’s has been investigated. This novel methodology was applied to convert substituted aryl bisulfite adducts to corresponding 5-arylidene-2,4-thiazolidinedione’s with POCl3 in less-polar solvents such as toluene, chlorobenzene and o-xylene. 5-(4-methoxybenzylidene)thiazolidine-2,4-dione and 5-(4-ethoxybenzylidene)thiazolidine-2,4-dione were obtained in good yields.

  通过芳香醛的亚硫酸氢盐加合物与噻唑烷-2,4-二酮的缩合反应形成碳-碳键以制备5-芳亚甲基-2,4-噻唑烷二酮的研究已经开展。这一新颖方法被应用于将取代的芳基亚硫酸氢盐加合物在较非极性溶剂如甲苯、氯苯和邻二甲苯中，使用POCl3转化为相应的5-芳亚甲基-2,4-噻唑烷二酮。5-(4-甲氧基苄叉基)噻唑烷-2,4-二酮和5-(4-乙氧基苄叉基)噻唑烷-2,4-二酮以良好产率获得。
• Selective C-H Fluorination of Pyridines and Diazines Inspired by a Classic Amination Reaction
  作者：Patrick S. Fier、John F. Hartwig

  DOI：10.1126/science.1243759

  日期：2013.11.22

  Fluorinating Pyridine Appending fluorine substituents to carbon centers is commonly used to tune small-molecule properties in pharmaceutical and agrochemical research. However, fluorinations often require the use of corrosive, hazardous reagents. Fier and Hartwig (p. 956) present an unusually mild and convenient protocol for fluorinating carbon sites adjacent to nitrogen in pyridines and related nitrogen-bearing

  氟化吡啶 将氟取代基附加到碳中心通常用于调节药物和农业化学研究中的小分子特性。然而，氟化通常需要使用腐蚀性、危险的试剂。Fier 和 Hartwig (p. 956) 提出了一种异常温和且方便的方案，用于氟化吡啶和相关含氮芳烃中与氮相邻的碳位点。该反应需要用二氟化银处理并在室温下快速进行。温和的氟化方法可以帮助生产医学研究中感兴趣的化合物。氟化杂环广泛存在于药物、农用化学品和材料中。然而，将氟结合到杂芳烃中的反应范围有限并且可能是危险的。我们提出了一种广泛适用且安全的方法，用于使用市售的氟化银 (II) 对吡啶和二嗪中的单个碳氢键进行位点选择性氟化。反应在环境温度下在 1 小时内发生，并且对氮附近的氟化具有唯一的选择性。温和的条件允许获得具有重要医学意义的化合物的氟化衍生物，以及通过随后的氟化物亲核置换制备的一系列 2-取代吡啶。机理研究表明，经典的吡啶胺化途径可适用于广泛范围的氮杂环的选择性氟化。反应在环境温度下在
• [EN] PROCESS FOR THE PREPARATION OF 5-[[4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY]PHENYL] METHYL]-2,4-THIAZOLIDINEDIONE<br/>[FR] PROCEDE SERVANT A PREPARER 5-[[4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY]PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE
  申请人：SUN PHARMACEUTICAL IND LTD

  公开号：WO2004108721A1

  公开（公告）日：2004-12-16

  A process for the preparation of 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione (formula 1) comprising a. reacting diazonium salt of 4-[2-(5-Ethyl-2-pyridyl) ethoxy] amino- benzene, compound of formula 2, with acrylamide, aqueous HX (wherein X is Br or Cl), under meerwein arylation conditions to yield compound of formula 3; b. condensing compound of formula 3 with thiourea to obtain compound of formula 4; and c. converting compound of formula 4 to compound of formula 1.

  一种制备5-[[4-[2-(5-乙基-2-吡啶基)乙氧基]苯基]甲基]-2,4-噻唑二酮（式1）的方法，包括a.将4-[2-(5-乙基-2-吡啶基)乙氧基]氨基苯的重氮盐（式2化合物）与丙烯酰胺、水溶HX（其中X为Br或Cl）在Meerwein芳基化条件下反应，得到式3化合物；b.将式3化合物与硫脲缩合得到式4化合物；c.将式4化合物转化为式1化合物。
• [EN] 5-(4-HYDROXYBENZYL)THIAZOLIDINE-2,4-DIONE AS INTERMEDIATE FOR SYNTHESIS OF THIAZOLIDINEDIONE BASED COMPOUNDS AND PROCESS FOR PREPARING THE SAME<br/>[FR] COMPOSÉ DE 5(4-HYDROXYBENZYL)THIAZOLIDINE-2,4-DIONE COMME PRODUIT INTERMÉDIAIRE DANS LA SYNTHÈSE DE COMPOSÉS À BASE DE THIAZOLIDINEDIONE ET PROCÉDÉ DE PRÉPARATION DE CELUI-CI
  申请人：DAEBONG LS LTD

  公开号：WO2009148195A1

  公开（公告）日：2009-12-10

  The present invention relates to 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by the following Chemical Formula [1], which is useful as an intermediate for synthesis of thiazolidinedione based compounds, a method for preparing the compound, and a method for preparing pioglitazone or pioglitazone hydrochloride, which is a thiazolidinedione based drug and useful in treating and preventing diabetes, using the 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by Chemical Formula [1] as an intermediate:

  本发明涉及以下化学式[1]所表示的5-(4-羟基苄基)噻唑烷-2,4-二酮，该化合物可用作合成噻唑烷二酮类化合物的中间体，以及制备该化合物的方法，以及制备吡格列酮或吡格列酮盐酸盐的方法。吡格列酮是一种基于噻唑烷二酮的药物，对治疗和预防糖尿病有用。利用化学式[1]表示的5-(4-羟基苄基)噻唑烷-2,4-二酮作为中间体。
• Pioglitazone impurities
  作者：Richter, Jindrich、Jirman、Havlicek、Hrdina

  DOI：10.1691/ph.2007.8.6720

  日期：——

  Methods of preparation of API pioglitazone were discussed from the point of view of impurities occurrence. Four real impurities (I–IV) of pioglitazone were prepared and characterized by means of NMR spectroscopy.

  从杂质出现的角度讨论了原料药吡格列酮的制备方法。制备了四种真正的吡格列酮杂质（I-IV），并通过核磁共振光谱进行了表征。