methyl D-glucarate-6,3-lactone | 155976-55-9

• 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-6,3-lactone
• 英文别名: methyl (2R)-2-[(2S,3R,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetate
• CAS: 155976-55-9
• 化学式: C₇H₁₀O₇
• 分子量: 206.152
• InChiKey: KIDJCDRSJYKKRK-LECHCGJUSA-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-6,3-lactone 在 氨 作用下， 以 甲醇 为溶剂， 以87.7%的产率得到D-glucaramide
  参考文献：
  名称：

  MM3(96) CONFORMATIONAL ANALYSIS OF d-GLUCARAMIDE AND X-RAY CRYSTAL STRUCTURES OF THREE d-GLUCARIC ACID DERIVATIVES—MODELS FOR SYNTHETIC POLY(ALKYLENE d-GLUCARAMIDES)

  摘要：

  An exhaustive conformational analysis Of D-glucaramide was carried out using MM3(96) [MM3(96). Molecular Mechanics Software used with permission from N.L. Allinger; University of Georgia]. Nine torsion angles were each driven in increments of 120degrees, generating 19,683 starting conformations. Each conformation was then fully energy-minimized using MM3's block diagonal/full matrix optimization option at dielectric constants of both 3.5 and 6.5. Conformer populations were calculated based on the modeling results and calculated theoretical average H-1 vicinal coupling constants were compared to experimental values obtained in D2O solution. Crystal structures of three acyclic D-glucaric acid derivatives (N,N'-dimethyl-D-glucaramide, dipotassium D-glucarate, and sodium potassium D-glucarate) are reported. These structures and that of previously reported monopotassiurn olucarate correspond closely with model conformations that were within one kcal/mol of the global minimum.

  DOI：

  10.1081/car-120003736
• 作为产物：
  描述：

  葡糖二酸 在 乙醚 、 丙酮 作用下， 生成 methyl D-glucarate-6,3-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

• 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。
• Zinner; Fischer, Chemische Berichte, 1956, vol. 89, p. 1503,1506
  作者：Zinner、Fischer

  DOI：——

  日期：——
• Saccharolactone Methyl Ester
  作者：Richard E. Reeves

  DOI：10.1021/ja01872a036

  日期：1939.3
• Hydroxylated nylons based on unprotected esterified D-glucaric acid by simple condensation reactions
  作者：D. E. Kiely、L. Chen、T. H. Lin

  DOI：10.1021/ja00081a018

  日期：1994.1

  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.
• Chen, Liang; Kiely, Donald E., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 4, p. 585 - 602
  作者：Chen, Liang、Kiely, Donald E.

  DOI：——

  日期：——