2-Methylfumaric acid (1-ethyl ester) | 89966-38-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Methylfumaric acid (1-ethyl ester)
• 英文别名: (E)-2-methylmonoethylfumarate；methyl-fumaric acid-1-ethyl ester；Methyl-fumarsaeure-1-aethylester；(E)-4-ethoxy-3-methyl-4-oxobut-2-enoic acid
• CAS: 89966-38-1
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: HWQBUJSWKVPMFY-SNAWJCMRSA-N

物化性质

• 沸点：
  273.5±23.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methylfumaric acid (1-ethyl ester) 在 氯化亚砜 、 硼烷四氢呋喃络合物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl (E)-4-chloro-2-methylbut-2-enoate
  参考文献：
  名称：

  甲基赤藓糖醇磷酸途径：LytB / IspH催化反应旋转的酶学证据。

  摘要：

  IspH / LytB是一种对氧敏感的[4Fe-4S]酶，催化甲基赤藓糖醇磷酸酯（MEP）途径的最后一步，这是开发新型抗微生物剂的目标。该金属酶将（E）-4-羟基-3-甲基丁-2-烯-1-基二磷酸酯（HMBPP）转化为两种类异戊二烯前体：异戊烯基二磷酸酯（IPP）和二甲基烯丙基二磷酸酯（DMAPP）。在此，报告了（S）-[4-2 H1] HMBPP和（R）-[4-2 H1] HMBPP的合成，以及在分别与大肠杆菌IspH /孵育后形成的产物的详细NMR分析。 LytB存在于大肠杆菌用于还原[4Fe-4S]中心的生物还原系统中。（S）-[4-2 H1] HMBPP转化为[4-2 H1] DMAPP和（E）-[4-2 H1] IPP，而（R）-[4-2 H1] HMBPP转化为[4- 2 H1] DMAPP和（Z）-[4-2 H1] IPP，

  DOI：

  10.1002/chem.201904676
• 作为产物：
  描述：

  ethyl (E)-4-hydroxy-2-methylbut-2-enoate 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以76%的产率得到2-Methylfumaric acid (1-ethyl ester)
  参考文献：
  名称：

  A ribozyme with michaelase activity

  摘要：

  The ability to generate RNA molecules that can catalyze complex organic transformations not only facilitates the reconstruction and plausibility of possible prebiotic reaction pathways but is also crucial for elucidating the potential of the application of RNA catalysts in organic syntheses. Iterative RNA selection previously identified a ribozyme that catalyzes the Michael addition of a cysteine thiol to an alpha,beta-unsaturated amide. This reaction is chemically similar to the rate limiting step of the thymidylate synthase reaction, which is the corresponding reaction of a cysteine thiol to the double-bond of the uracil nucleobase. Here we provide a detailed description of the synthesis of the ribozyme substrates and the substrate oligonucleotides used for its characterization and the investigation of the background reaction. We also describe the further characterization of the ribozyme with respect to substrate specificity. We show that the thiol group of the cysteine nucleophile is essential for the reaction to proceed. When substituted for a thiomethyl group, no reaction takes place. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00311-5

文献信息

• Regioselective hydrolysis of diesters of (Z)- and (E)-2-methyl-butenedioic acids by PLE
  作者：Rudolf Schmid、Vassilia Partali、Thorleif Anthonsen、Henrik W Anthonsen、Lise Kvittingen

  DOI：10.1016/s0040-4039(01)01834-2

  日期：2001.11

  (Z)- and (E)-2-methyl-butenedioic acids (citraconic and mesaconic acid) were hydrolysed by pig live esterase, PLE. For the diethyl esters the enzyme showed low regioselectivity for both the (Z)- and the (E)-isomers. However, the hydrolysis of dimethyl and dipropyl (Z)-2-methyl-butenedioic acid gave a ratio of the monoesters of 95:5 and 85:15.

  （Z）-和（E）-2-甲基-丁烯二酸（柠康酸和中康酸）的二甲酯，二乙酯和二丙酯被猪活酯酶PLE水解。对于二乙酯，该酶对（Z）-和（E）-异构体均显示低的区域选择性。然而，二甲基和二丙基（Z）-2-甲基丁烯二酸的水解给出单酯的比例为95：5和85:15。
• Domino condensation/aza-Michael/O→N acyl migration of carbodiimides with activated α,β-unsaturated carboxylic acids to form hydantoins
  作者：Alessandro Volonterio、Matteo Zanda

  DOI：10.1016/j.tetlet.2003.09.134

  日期：2003.11

  Activated α,β-unsaturated carboxylic acids undergo an unexpected domino condensation/aza-Michael/O→N acyl migration with carbodiimides, producing N,N-disubstituted hydantoins in good yields. An array of structurally varied aspartic acid-derived hydantoins, including some fluorinated derivatives, have been synthesized by this method, whose scope and limits are discussed.

  活化的α，β-不饱和羧酸与碳二亚胺发生意想不到的多米诺骨牌缩合/氮杂-迈克尔/ O→N酰基迁移，以高收率生产N，N-二取代的乙内酰脲。通过该方法合成了一系列结构变化的天冬氨酸衍生的乙内酰脲，包括一些氟化衍生物，并讨论了其范围和限制。
• [EN] PHARMACEUTICAL COMPOSITIONS CONTAINING DIMETHYL FUMARATE<br/>[FR] COMPOSITIONS PHARMACEUTIQUES CONTENANT DU FUMARATE DE DIMÉTHYLE
  申请人：BIOGEN IDEC INC

  公开号：WO2013119677A1

  公开（公告）日：2013-08-15

  Provided herein are compositions containing compounds, or pharmaceutically acceptable salts, that metabolize to monomethyl fumarate with certain pharmacokinetic parameters and methods for treating, prophylaxis, or amelioration of neurodegenerative diseases including multiple sclerosis using such compositions in a subject, wherein if the compositions contain dimethyl fumarate, the total amount of dimethyl fumarate in the compositions ranges from about 43% w/w to about 95% w/w.

  本文提供了一些含有化合物或药学上可接受的盐的组合物，这些化合物具有特定的药代动力学参数，可以代谢成单甲基富马酸，并且提供了使用这些组合物在受试者中治疗、预防或缓解神经退行性疾病，包括多发性硬化症的方法。如果这些组合物包含二甲基富马酸，则二甲基富马酸的总含量在43% w/w至95% w/w范围内。
• Coating varnish composition and antifouling coating composition
  申请人：Hitachi Chemical Co., Ltd.

  公开号：EP0711813A2

  公开（公告）日：1996-05-15

  A coating varnish composition comprising a biodegradable polymer (A) comprising one or more kinds of constituent units (b) represented by the general formula (I), (II) or (III) and one or more other kinds of constituent units (a) capable of imparting bio-degradability: wherein in the formula (I), R¹ and R are independently a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group or a phenyl group; in the formula (II), R³ and R⁴ are independently a hydrogen atom, a chlorine atom, a bromine atom, or a substituted or unsubstituted methyl or ethyl group; in the formula (III), R⁵ and R⁶ are independently a hydrogen atom, a methyl group or an ethyl group, and R⁷ is a straight, branched or cyclic alkyl group, an aryl group, a heterocyclic group or an aralkyl group, which may have one or more substituents.

  一种涂料清漆组合物，包含一种可生物降解聚合物 (A)，该聚合物包含一种或多种由通式 (I)、(II) 或 (III) 表示的组成单元 (b) 和一种或多种可赋予生物降解性的其他组成单元 (a)： 其中，在式 (I) 中，R¹ 和 R 独立地为氢原子、氯原子、溴原子、甲基、乙基或苯基；在式 (II) 中，R³ 和 R⁴ 独立地为氢原子、氯原子、溴原子或取代或未取代的甲基或乙基；在式 (III) 中，R⁵ 和 R⁶ 独立地是氢原子、甲基或乙基，R⁷ 是直链、支链或环状烷基、芳基、杂环基或芳烷基，它们可以有一个或多个取代基。
• Dimethyl fumarate and vaccination regimens
  申请人：Biogen MA Inc.

  公开号：US10555993B2

  公开（公告）日：2020-02-11

  Provided herein is a method of treating or preventing a disease or disorder (e.g., MS) in a subject in need thereof, comprising (a) administering to the subject a first dose of a pharmaceutical composition comprising a fumarate agent (e.g., DMF) for a first dosing period; (b) administering a vaccine; and (c) administering to the subject a second dose of the pharmaceutical composition for a second dosing period.

  本文提供了一种在有需要的受试者中治疗或预防疾病或紊乱（如多发性硬化症）的方法，包括(a)在第一给药期向受试者施用第一剂量的包含富马酸剂（如DMF）的药物组合物；(b)施用疫苗；以及(c)在第二给药期向受试者施用第二剂量的药物组合物。