5-(4-methoxybenzyl)thiazolidine-2,4-dione | 184840-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxybenzyl)thiazolidine-2,4-dione
• 英文别名: 5-[(4-methoxyphenyl)-methyl]thiazolidine-2,4-dione；5-[(4-Methoxyphenyl)methyl]thiazolidine-2,4-dione；5-[(4-methoxyphenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 184840-77-5
• 化学式: C₁₁H₁₁NO₃S
• 分子量: 237.279
• InChiKey: MLEYEAMBTJOEKR-UHFFFAOYSA-N

物化性质

• 熔点：
  111.5-113.6 °C
• 沸点：
  430.3±18.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-methoxybenzyl)thiazolidine-2,4-dione 在 三溴化硼 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 5-(4-羟基苄基)噻唑烷-2,4-二酮
  参考文献：
  名称：

  Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis

  摘要：

  该发明提供了在治疗2型糖尿病中有用的药物化合物。这些化合物具有优势，因为它们可以被代谢药物解毒系统迅速代谢。特别地，设计了在化合物结构中包含酯的噻唑烷二酮类似物。该发明还涉及治疗疾病的方法，如糖尿病，包括给予经设计为能够被血清或细胞内水解酶和酯酶代谢的化合物的治疗有效组合物。还教授了含酯基噻唑烷二酮类似物的药物组合物。

  公开号：

  US06958355B2
• 作为产物：
  描述：

  5-P-甲氧基苄亚基-2,4-噻唑烷二酮 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲酸 为溶剂， 22.84 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 5-(4-methoxybenzyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  5-亚烷基-2,4-噻唑烷二酮在温和条件下在 Pd/C 催化剂上加氢：吡格列酮的替代合成路线

  摘要：

  使用 Pd/C 研究 5-亚烷基-2,4-噻唑烷二酮的氢化，以建立吡格列酮合成的替代工艺。据报道，反应缓慢是由于甲酸的反应温度高。在 296 K 条件下将条件提高到 1 个大气压，这导致使用较少量催化剂的定量产品。图形摘要

  DOI：

  10.1007/s10562-013-0976-8

文献信息

• Processes for making pioglitazone and compounds of the processes
  申请人：Zhu Jie

  公开号：US20070167629A1

  公开（公告）日：2007-07-19

  Pioglitazone can be made via a Darzens Condensation reaction in an industrially useful process.

  Pioglitazone可以通过Darzens缩合反应在工业上进行制备。
• ピオグリタゾン塩酸塩の製造方法
  申请人：株式会社トクヤマ

  公开号：JP2009013091A

  公开（公告）日：2009-01-22

  PROBLEM TO BE SOLVED: To inexpensively produce pioglitazone hydrochloride using a reduced number of reaction steps.

  SOLUTION: Pioglitazone hydrochloride represented by the formula is produced by causing p-methoxybenzyl halide to react with thiazolidinedione to synthesize 5-(4-methoxybenzyl)-2,4-thiazolidinedione, demethylating the thus-obtained 5-(4-methoxybenzyl)-2,4-thiazolidinedione by causing hydrogen bromide to react therewith to obtain 5-(4-hydroxybenzyl)-2,4-thiazolidinedione, further causing this product to react with 5-ethyl-2-(2-chloroethyl)pyridine, to give 5-ä4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione, and then causing this product to react with hydrogen chloride.

  COPYRIGHT: (C)2009,JPO&INPIT

  要解决的问题：以较少的反应步骤低成本生产吡格列酮盐酸盐。 解决方案：通过使对甲氧基苄基卤化物与噻唑烷二酮反应合成5-(4-甲氧基苄基)-2,4-噻唑烷二酮，使得得到的5-(4-甲氧基苄基)-2,4-噻唑烷二酮与氢溴酸反应去甲基化，得到5-(4-羟基苄基)-2,4-噻唑烷二酮，进一步使该产物与5-乙基-2-(2-氯乙基)吡啶反应，得到5-(4-【2-(5-乙基-2-吡啶基)乙氧基】苄基)-2,4-噻唑烷二酮，然后使该产物与氯化氢反应，生产吡格列酮盐酸盐。 版权：(C)2009，JPO&INPIT
• Substituted benzylthiazolidine-2, 4-dione derivatives
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US06730687B1

  公开（公告）日：2004-05-04

  The invention provides novel substituted benzylthiazolidine-2,4-dione derivatives that bind to receptor to activate as ligands of human peroxisome proliferator-activated receptor (PPAR) and exhibit blood glucose-decreasing action and lipid-decreasing action, and processes for preparing them. It relates to substituted benzylthiazolidine-2,4-dione derivatives represented by the general formula (1) [wherein the bond mode of A denotes —CH2CONH—, —NHCONH—, —CH2CH2CO— or —NHCOCH2—, and B denotes a lower alkyl group with carbon atoms of 1 to 4, lower alkoxy group with carbon atoms of 1 to 3, halogen atom, trifluoromethyl group, trifluoromethoxy group, phenyl group which is unsubstituted or may have substituents, phenoxy group which is unsubstituted or may have substituents or benzyloxy group which is unsubstituted or may have substituents], their medicinally acceptable salts, their hydrates and processes for preparing them.

  该发明提供了新型的取代苯基噻唑烷-2,4-二酮衍生物，其结合受体以激活人类过氧化物酶体增殖物激活受体（PPAR）作为配体，并表现出降低血糖和降低脂质的作用，以及制备它们的过程。它涉及由通式（1）所表示的取代苯基噻唑烷-2,4-二酮衍生物 [其中，A的键合模式表示为—CH2CONH—、—NHCONH—、—CH2CH2CO—或—NHCOCH2—，B表示碳原子为1到4的低碳基，碳原子为1到3的低碳氧基，卤素原子，三氟甲基基团，三氟甲氧基团，苯基未取代或可能有取代基，苯氧基未取代或可能有取代基或苄氧基未取代或可能有取代基]，其医学上可接受的盐，其水合物和制备它们的过程。
• Photocatalytic Radical Coupling of Organoborates with α-Halogenated Electron-Poor Olefins
  作者：Marina Caldarelli、Sarah Jane Rezzi、Nicoletta Colombo、Tracey Pirali、Gianluca Papeo

  DOI：10.1021/acs.joc.3c02386

  日期：2024.1.5

  Herein, we report the visible-light-mediated addition of organoborates to α-halogenated electron-poor olefins enabled by an environmentally benign metal-free catalyst. The method accommodates a variety of boronic acid derivatives as well as alkenes and delivers the corresponding saturated α-halo-derivatives in up to 90% yields. The obtained products are high-value building blocks in organic synthesis

  在此，我们报告了通过环境友好的无金属催化剂实现的可见光介导的有机硼酸盐与α-卤代贫电子烯烃的加成。该方法适用于各种硼酸衍生物以及烯烃，并以高达 90% 的产率提供相应的饱和 α-卤代衍生物。所得产品是有机合成中的高价值构建模块，可进行各种后续转化。
• PROCESS FOR PRODUCING THIAZOLIDINEDIONE COMPOUND AND PRODUCTION INTERMEDIATE THEREOF
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1894929A1

  公开（公告）日：2008-03-05

  There are provided crystals of a thiazolidinedione derivative having excellent prophylactic and therapeutic effects on a disease caused by insulin resistance and a process for producing the thiazolidinedione derivative with a high purity. A process for producing a compound represented by the general formula (A) or a salt thereof, comprising converting 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid represented by the following formula into a compound of the general formula (I), wherein X = a halogen atom; then reacting the compound with a compound represented by the general formula (II), wherein R1, R2, R3 and R4 = a hydrogen atom, a hydroxyl group, C1-C6 alkyl, C1-C6 alkoxy, benzyloxy, acetoxy, trifluoromethyl or a halogen atom, R5 = C1-C6 alkyl, and R6 = a protecting group for an amino group, to produce a compound represented by the general formula (III); and subsequently cyclizing the compound into the final product, and crystals of a compound represented by the general formula (A) or a salt thereof.

  本发明提供了一种对胰岛素抵抗引起的疾病具有良好预防和治疗效果的噻唑烷二酮衍生物晶体，以及一种高纯度噻唑烷二酮衍生物的生产工艺。一种生产通式(A)所代表的化合物或其盐的工艺，包括将下式所代表的 4-[(2,4-二氧代噻唑烷-5-基)甲基]苯氧乙酸转化为通式(I)的化合物，其中 X＝卤素原子；然后将该化合物与通式 (II) 所代表的化合物反应，其中 R1、R2、R3 和 R4 = 氢原子、羟基、C1-C6 烷基、C1-C6 烷氧基、苄氧基、乙酰氧基、三氟甲基或卤原子，R5 = C1-C6 烷基，R6 = 氨基的保护基团，生成通式 (III) 所代表的化合物；然后将该化合物环化成最终产物，以及通式 (A) 所代表的化合物或其盐的结晶。