二甲基马来酸2,3-二甲基顺丁烯二酸 | 488-21-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 二甲基马来酸2,3-二甲基顺丁烯二酸
• 中文别名: 2,3-二甲基马来酸
• 英文名称: 2,3-dimethylmaleic acid
• 英文别名: cis-2,3-dimethylbutenedioic acid；acide dimethylmaleique；Dimethylmaleic acid；methylcitraconic acid；(Z)-2,3-dimethylbut-2-enedioic acid
• CAS: 488-21-1
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: CGBYBGVMDAPUIH-ARJAWSKDSA-N

物化性质

• 稳定性/保质期：

  存在于白肋烟和香料烟的烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

制备方法

• 烟草: BU,56; OR,44。

合成制备方法

• 烟草：BU，56；OR，44。

用途简介

（暂无内容）

反应信息

• 作为反应物：
  描述：

  二甲基马来酸2,3-二甲基顺丁烯二酸 生成 2,3-二甲基马来酸酐
  参考文献：
  名称：

  Dicarboxylic Acids Link Proton Transfer Across a Liquid Membrane to the Synthesis of Acyl Phosphates. A Model for P-Type H+-ATPases

  摘要：

  H+-ATPases are ion pumps that link proton transfer across cell membranes to the synthesis or hydrolysis of ATP. A current research goal is to understand the molecular-level mechanism of this linking. We present a chemical model that mimics some features of H+-ATPases by linking proton transfer across a liquid membrane to the synthesis of acyl phosphates using carboxylic acid anhydride intermediates. Citraconic acid (cis-2-methyl-2-butenedioic acid) accelerated the transfer of protons from a pH 0.3 solution across a chloroform liquid membrane to a pH 10 solution. The mechanism involved spontaneous formation of a small amount of citraconic anhydride (0.6%) in the pH 0.3 layer. This anhydride partitioned into the chloroform layer and diffused to the pH 10 layer, where it hydrolyzed, generating two protons. When the pH 10 layer contained phosphate (1.0 M), some of the citraconic anhydride reacted with phosphate to form citraconyl phosphate, 5.0% yield. In separate experiments, we confirmed that citraconyl phosphate had high phosphoryl donor potential by reacting it with morpholine to form a phosphoramidate (11.5% yield) or with fluoride to form fluorophosphonate (32% yield). To demonstrate the link between an acyl phosphate and a proton gradient in the reverse direction, we used succinyl phosphate, whose hydrolysis occurs in two steps: formation of succinic anhydride, which consumes protons, followed by hydrolysis of succinic anhydride, which releases protons. We generated a pH gradient by carrying out these two steps in separate solutions. Hydrolysis of succinyl phosphate (3.9 mmol) at pH 6.00 started with a increase in pH to 6.16 (0.59 mmol of H+ consumed) caused by the formation of succinic anhydride. We extracted this anhydride with dichloromethane and transferred it to a separate solution at pH 6.05. Hydrolysis of the anhydride released protons (0.36 mmol), decreasing the pH to 5.23. Our model suggests that H+-ATPases could use acyl phosphates and carboxylic acid anhydride intermediates to link proton transfer to ATP synthesis or hydrolysis.

  DOI：

  10.1021/jo00092a023
• 作为产物：
  描述：

  2,3-二甲基马来酸酐 在 水 作用下， 生成 二甲基马来酸2,3-二甲基顺丁烯二酸
  参考文献：
  名称：

  单和二烷基取代的马来酰胺酸的合成及pH依赖的水解曲线

  摘要：

  马来酰胺酸衍生物作为弱酸敏感性连接基或笼蔽基团已广泛用于智能递送系统中。在这里，我们报告了单-和二烷基取代的马来酰胺酸的受控合成方法及其pH依赖的水解行为。首先，我们研究了正丁胺与柠康酸酐之间的反应，发现可以通过控制反应温度和时间来精细调节两种正丁基柠康酸异构体（α和β）的比例。其次，我们研究了溶剂，碱性催化剂和温度对n反应的影响丁胺与2,3-二甲基马来酸酐的反应，并优化了反应条件以有效合成二甲基马来酰胺酸。最后，我们比较了四种OEG-NH 2衍生的水溶性马来酰胺酸衍生物的pH依赖性水解曲线。结果表明，顺式-双键上的取代基的数量，结构和位置对pH相关的水解动力学和马来酰胺衍生物的选择性表现出显着的影响。有趣的是，对于单取代的柠康酸（α-/β-异构体），我们发现它们的水解伴随着两种异构体之间的异构化。

  DOI：

  10.1039/c7ob02188g

文献信息

• [EN] CRYSTALLINE FORM OF QUINAPRIL HYDROCHLORIDE AND PROCESS FOR PREPARING THE SAME<br/>[FR] FORME CRISTALLINE D'UN HYDROCHLORURE DE QUINAPRIL ET PROCEDE DE PREPARATION DE CELLE-CI
  申请人：LUPIN LTD

  公开号：WO2004054980A1

  公开（公告）日：2004-07-01

  A novel crystalline form of quinapril hydrochloride of formula (I). An amorphous form of quinapril hydrochloride substantially free of impurities, specially diketopiperazine compound, and conforming to pharmacopoeial specifications formed from the said novel crystalline form of quinapril hydrochloride of formula (I). The crystalline quinapril hydrochloride is in the form nitroalkane solvate in which the nitroalkane is nitromethane, nitroethane and nitropropane. Each such nitroalkane solvate having particular characteristic X- ray diffraction patterns. A process for preparation of amorphous from of quinapril hydrochloride, substantially free of impurities, specially diketopiperazine compound, and conforming to pharmacopoeial specifications, using the novel crystalline quinapril hydrochloride as an intermediate. The process involves obtaining free base compound of formula (V) by adjusting the pH of a solution of the benzyl ester maleate salt of quinapril of formula (V) between 7.5-8.5 in a mixture of water and an organic solvent; catalytic hydrogenation of this compound (V) in an alcoholic solvent in the presence of concentrated hydrochloric acid or hydrogen chloride dissolved in an alcoholic solvent and in the presence of catalytic amounts of Pd/C to obtain a residue containing formula (I); crystallization of the said residue by evaporating the alcoholic solvent from a nitroalkane solvent to give crystalline quinapril hydrochloride, associated with a solvate of the nitroalkane solvent, and drying the crystalline quinapril hydrochloride nitroalkane solvate at a temperature between 40°C and 45°C under vacuum to give amorphous quinapril hydrochloride of formula (I).

  盐酸喹那普利的一种新颖结晶形式，其化学式为(I)。一种基本上无杂质的盐酸喹那普利无定形形式，特别是二酮哌嗪化合物，并且符合药典规格，由所述的盐酸喹那普利新颖结晶形式（化学式为I）形成。该结晶形式的盐酸喹那普利是以硝基烷为溶剂的溶剂化物，其中硝基烷是硝基甲烷、硝基乙烷和硝基丙烷。每一种这样的硝基烷溶剂化物都具有特定的特征X-射线衍射图谱。一种制备基本上无杂质，特别是二酮哌嗪化合物，并符合药典规格的盐酸喹那普利无定形形式的过程，使用新颖的结晶盐酸喹那普利作为中间体。该过程包括通过将喹那普利苯甲基酯马来酸盐（化学式为V）的水和有机溶剂混合溶液的pH值调整在7.5-8.5之间，获得自由碱化合物（化学式为V）；在醇溶剂中对该化合物（V）进行催化氢化，在浓盐酸或溶于醇溶剂中的氯化氢的存在下，以及在Pd/C的催化量存在下，获得含有化学式（I）的残留物；通过从硝基烷溶剂中蒸发醇溶剂使所述残留物结晶，得到与硝基烷溶剂的溶剂化物相关的结晶盐酸喹那普利，并在40°C至45°C的温度下，在真空下干燥结晶盐酸喹那普利硝基烷溶剂化物，得到无定形的盐酸喹那普利（化学式为I）。
• [EN] DISUBSTITUTED MALEIC ANHYDRIDES WITH ALTERED KINETICS OF RING CLOSURE<br/>[FR] ANHYDRIDES MALÉIQUES DISUBSTITUÉS AYANT UNE CINÉTIQUE MODIFIÉ DE FERMETURE DE CYCLE
  申请人：ARROWHEAD MADISON INC

  公开号：WO2012173784A1

  公开（公告）日：2012-12-20

  We describe anhydride compounds suitable for physiologically labile modification of amine- containing molecules. The described anhydrides form reversible linkages having desirable kinetics for in vivo delivery of biologically active molecules. Also described are endosomolytic polymers formed by modification of membrane active polyamines with the described anhydrides.

  我们描述了适用于生理易降解修饰胺基含有分子的酐化合物。所述的酐形成可逆连接，具有适合体内传递生物活性分子的理想动力学特性。还描述了通过修饰膜活性多胺与所述酐化合物形成的内体溶解聚合物。
• [EN] PROCESS FOR THE PREPARATION OF AGOMELATINE IN CRYSTALLINE FORM<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AGOMÉLATINE SOUS FORME CRISTALLINE
  申请人：KRKA D D NOVO MESTO

  公开号：WO2019072864A1

  公开（公告）日：2019-04-18

  The present invention pertains to a process for the preparation of polymorph form X of agomelatine, which comprises providing agomelatine, and crystallizing agomelatine in the presence of at least one of an acid and a salt thereof, and to a polymorph form of agomelatine.

  本发明涉及一种制备阿戈美拉汀多晶型X的方法，包括提供阿戈美拉汀，并在酸和/或其盐的存在下结晶阿戈美拉汀，以及阿戈美拉汀的多晶型。
• [EN] MICROORGANISMS FOR PRODUCING 4C-5C COMPOUNDS WITH UNSATURATION AND METHODS RELATED THERETO<br/>[FR] MICRO-ORGANISMES POUR LA PRODUCTION DE COMPOSÉS EN 4C-5 C AVEC UNE INSATURATION ET PROCÉDÉS ASSOCIÉS
  申请人：GENOMATICA INC

  公开号：WO2016004334A1

  公开（公告）日：2016-01-07

  The invention provides a non-naturally occurring microbial organism having a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol, pathway. The microbial organism contains at least one exogenous nucleic acid encoding an enzyme in a pathway. The invention additionally provides a method for producing butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol,. The method can include culturing a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol-producing microbial organism, where the microbial organism expresses at least one exogenous nucleic acid encoding a pathway enzyme in a sufficient amount, and under conditions and for a sufficient period of time to produce butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol.

  该发明提供了一种具有丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇途径的非自然微生物生物体。该微生物生物体含有至少一个编码途径中酶的外源核酸。该发明还提供了一种生产丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇的方法。该方法可以包括培养一种生产丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇的微生物生物体，其中该微生物生物体表达至少一个编码途径酶的外源核酸，且在足够的量下，在适当的条件和足够的时间内产生丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇。
• [EN] NANOPARTICLE, LIPOSOMES, POLYMERS, AGENTS AND PROTEINS MODIFIED WITH REVERSIBLE LINKERS<br/>[FR] NANOPARTICULES, LIPOSOMES, POLYMÈRES, AGENTS ET PROTÉINES MODIFIÉS AVEC DES LIEURS RÉVERSIBLES
  申请人：UNIV NORTH CAROLINA

  公开号：WO2012112689A1

  公开（公告）日：2012-08-23

  Pharmaceutical, chemical and biological agents containing a reversible disulfide linker are described. These agents can also be covalently bound or contained in delivery vehicles for delivering the agents to desired targets or areas. Also described are delivery vehicles which contain an agent having a reversible disulfide linker and to vehicles that are covalently linked to the agent containing a reversible disulfide linker. The modifications described herein can modify properties of the agents and vehicles, thereby providing desired solubility, stability, hydrophobicity and targeting while the reversibility of the linker can leave the agent to which it is attached free from residual chemical groups after being reduced.

  描述了含有可逆二硫键的药物、化学物质和生物制剂。这些制剂也可以共价结合或包含在传递载体中，以将制剂传递到所需的靶标或区域。还描述了含有可逆二硫键的制剂的传递载体，以及与含有可逆二硫键的制剂共价结合的载体。本文描述的修饰可以改变制剂和载体的性质，从而提供所需的溶解性、稳定性、疏水性和靶向性，而连接物的可逆性可以使其附着的制剂在还原后不受残留化学基团的影响。