methyl D-glucarate 1,4-lactone | 22140-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: methyl D-glucarate 1,4-lactone
• 英文别名: methyl D-glucarate-1,4-lactone；D-glucaric acid-1=>4-lactone-6-methyl ester；D-Glucarsaeure-1=>4-lacton-6-methylester；methyl (2S)-2-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetate
• CAS: 22140-16-5
• 化学式: C₇H₁₀O₇
• 分子量: 206.152
• InChiKey: KIDJCDRSJYKKRK-MBMOQRBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl D-glucarate 1,4-lactone 反应 12.0h， 以98%的产率得到D-glucaro-1,4:6,3-dilactone
  参考文献：
  名称：

  Hydroxylated nylons based on unprotected esterified D-glucaric acid by simple condensation reactions

  摘要：

  Convenient procedures are described for the preparation of hydroxylated nylons (polyhydroxypolyamides) from D-glucaric acid. The procedures, which do not require protection/deprotection of carbohydrate hydroxyl groups, can be used to make a variety of polymers with a range of properties from D-glucaric acid. Simple alcohol (e.g. methanol or ethanol) esterification mixtures of D-glucaric acid (from oxidation of D-glucose) were reacted with bis-primary diamines in a polar solvent, typically methanol, to produce the polyamides. D-Glucaric acid esterification mixtures contain varying amounts of dialkyl D-glucarate, alkyl D-glucarate 1,4-lactone, and alkyl D-glucarate 6,3-lactone. These ester forms of D-glucaric acid are also in equilibrium under the conditions of the polymerization. Diamines employed included linear alkylenediamines, a branched alkylenediamine, arylalkylenediamines, and diamines with oxygen or nitrogen atoms in the alkylene chain. Considerable differences in polymer physical properties were observed by changing the diamine monomer. Linear aliphatic and arylalkylenediamines gave crystalline solid polyamides with high melting points. The C2 and C4 diamine copolymers were water soluble, whereas the C6 and above were water insoluble. The branched diamine copolymer and those with oxygen or nitrogen in the diamine chain had lower melting points and higher alcohol solubility than the unbranched alkylenediamine copolymers.

  DOI：

  10.1021/ja00081a018
• 作为产物：
  描述：

  葡糖二酸 在 乙醚 、 丙酮 作用下， 生成 methyl D-glucarate 1,4-lactone
  参考文献：
  名称：

  173.葡萄糖酸内酯。第三部分 单和双内酯

  摘要：

  DOI：

  10.1039/jr9440000633

文献信息

• Hydrogen Gas-Mediated Deoxydehydration/Hydrogenation of Sugar Acids: Catalytic Conversion of Glucarates to Adipates
  作者：Reed T. Larson、Andrew Samant、Jianbin Chen、Woojin Lee、Martin A. Bohn、Dominik M. Ohlmann、Stephan J. Zuend、F. Dean Toste

  DOI：10.1021/jacs.7b07801

  日期：2017.10.11

  of polyhydroxylated biomass into industrially relevant feedstock chemicals is described. This system includes a bimetallic Pd/Re catalyst in combination with hydrogen gas as a terminal reductant and enables the high-yielding reduction of sugar acids. This procedure has been applied to the synthesis of adipate esters, precursors for the production of Nylon-6,6, in excellent yield from biomass-derived

  描述了用于将多羟基化生物质转化为工业相关原料化学品的操作简单、可扩展的系统的开发。该系统包括双金属 Pd/Re 催化剂和作为末端还原剂的氢气，能够实现糖酸的高产还原。该程序已应用于合成己二酸酯，即生产尼龙 6,6 的前体，从生物质来源中以优异的产量合成。
• Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass
  作者：Weiping Deng、Longfei Yan、Binju Wang、Qihui Zhang、Haiyan Song、Shanshan Wang、Qinghong Zhang、Ye Wang

  DOI：10.1002/anie.202013843

  日期：2021.2.23

  adipic acid from renewable biomass is a very attractive goal of sustainable chemistry. Herein, we report efficient catalysts for a two‐step transformation of cellulose‐derived glucose into adipic acid via glucaric acid. Carbon nanotube‐supported platinum nanoparticles are found to work efficiently for the oxidation of glucose to glucaric acid. An activated carbon‐supported bifunctional catalyst composed

  由可再生生物质绿色合成己二酸是可持续化学的一个非常诱人的目标。本文中，我们报道了通过葡糖二酸将纤维素衍生的葡萄糖分两步转化为己二酸的有效催化剂。发现碳纳米管支持的铂纳米颗粒可有效地将葡萄糖氧化为葡糖二酸。发现由氧化rh和钯组成的活性炭负载双功能催化剂可有效去除葡糖二酸中的四个羟基，可提供99％的己二酸收率。氧化hen具有脱氧功能，但去除四个羟基的效率较低。钯的共存不仅催化烯烃中间体的加氢，而且协同促进脱氧。
• Hydroxypolyamide Gel Forming Agents
  申请人：Kiely Donald E.

  公开号：US20090131259A1

  公开（公告）日：2009-05-21

  Hydroxypolyamides, hydroxypolyamide products, and post-hydroxypolyamides are disclosed as gel forming agents. Hydroxypolyamides and post-hydroxypolyamides are prepared from known methods. Hydroxypolyamide products are produced from a modified polymerization procedure which utilizes strong base for deprotonation of ammonium salts from the esterification of stoichiometrically equivalent polyacid:polyamine salts. The hydroxypolyamide products are capable of gel formation at lower concentrations than hydroxypolyamides and post-hydroxypolyamides from the known methods of preparation, and are therefore superior gel forming agents.

  本发明公开了羟基聚酰胺、羟基聚酰胺产品和后处理羟基聚酰胺作为凝胶形成剂。羟基聚酰胺和后处理羟基聚酰胺是通过已知的方法制备的。羟基聚酰胺产品是通过改进的聚合程序制备的，该程序利用强碱去质子化酯化反应中的聚酸：聚胺盐的铵盐。羟基聚酰胺产品能够在较低浓度下形成凝胶，比通过已知制备方法制备的羟基聚酰胺和后处理羟基聚酰胺更为优越，因此是优良的凝胶形成剂。
• Hydroxypolyamide gel forming agents
  申请人：Kiely Donald E.

  公开号：US08623943B2

  公开（公告）日：2014-01-07

  Hydroxypolyamides, hydroxypolyamide products, and post-hydroxypolyamides are disclosed as gel forming agents. Hydroxypolyamides and post-hydroxypolyamides are prepared from known methods. Hydroxypolyamide products are produced from a modified polymerization procedure which utilizes strong base for deprotonation of ammonium salts from the esterification of stoichiometrically equivalent polyacid:polyamine salts. The hydroxypolyamide products are capable of gel formation at lower concentrations than hydroxypolyamides and post-hydroxypolyamides from the known methods of preparation, and are therefore superior gel forming agents.

  本发明涉及羟基聚酰胺、羟基聚酰胺产品和后处理羟基聚酰胺作为凝胶形成剂。羟基聚酰胺和后处理羟基聚酰胺是通过已知方法制备的。羟基聚酰胺产品是通过一种改良的聚合方法生产的，该方法利用强碱去质子化酯化的化学计量比等量的多酸多胺盐中的铵盐。羟基聚酰胺产品能够在较低的浓度下形成凝胶，比通过已知制备方法制备的羟基聚酰胺和后处理羟基聚酰胺更优秀。
• HYDROXYPOLYAMIDE GEL FORMING AGENTS
  申请人：THE UNIVERSITY OF MONTANA

  公开号：US20140228452A1

  公开（公告）日：2014-08-14

  Hydroxypolyamides, hydroxypolyamide products, and post-hydroxypolyamides are disclosed as gel forming agents. Hydroxypolyamides and post-hydroxypolyamides are prepared from known methods. Hydroxypolyamide products are produced from a modified polymerization procedure which utilizes strong base for deprotonation of ammonium salts from the esterification of stoichiometrically equivalent polyacid:polyamine salts. The hydroxypolyamide products are capable of gel formation at lower concentrations than hydroxypolyamides and post-hydroxypolyamides from the known methods of preparation, and are therefore superior gel forming agents.

  本发明公开了羟基聚酰胺、羟基聚酰胺产品和后处理羟基聚酰胺作为凝胶形成剂。羟基聚酰胺和后处理羟基聚酰胺是通过已知方法制备的。羟基聚酰胺产品是通过改进的聚合程序生产的，该程序利用强碱去质子化聚酸：聚胺盐的酯化反应。与已知制备方法的羟基聚酰胺和后处理羟基聚酰胺相比，羟基聚酰胺产品在较低浓度下就能形成凝胶，因此是更优秀的凝胶形成剂。