N,N'-dipropyl-D-glucaramide | 108991-69-1

• 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: N,N'-dipropyl-D-glucaramide
• 英文别名: N,N'-dipropyl-D-glucaramide；N,N'-Dipropyl-D-glucaramid；D-Glucarsaeure-bis-propylamid；(2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-N,N'-dipropylhexanediamide
• CAS: 108991-69-1
• 化学式: C₁₂H₂₄N₂O₆
• 分子量: 292.332
• InChiKey: MGUNSVQZAJGRKX-AATLWQCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  正丙胺 、 D-glucaro-1,4:6,3-dilactone 以 甲醇 为溶剂， 反应 3.0h， 以96%的产率得到N,N'-dipropyl-D-glucaramide
  参考文献：
  名称：

  Mechanisms for the Formation of Diamides and Polyamides by Aminolysis of d‐Glucaric Acid Esters

  摘要：

  H-1 and C-13 NMR were employed to chart the conversion of the five-membered lactone esters methyl D-glucarate 1,4-lactone (1) and ethyl D-glucarate 6,3-lactone (5) to N,N'-dipropyl-D-glucaramide with n-propylamine in DMSO-d(6). These experiments were carried out to model the amide forming steps in polycondensation reactions between esterified D-glucaric acid and diamines to give poly(D-glucaramides). It was clear from the resulting NMR spectra that the lactones 1 and 5 were each converted in three consecutive steps to the product diamides; aminolysis of the lactone ester to the corresponding acyclic N-propyl-D-glucaramide monoester, followed by lactonization to a five-membered lactone amide, and concluding with aminolyis of the lactone amide to N,N'-dipropyl-D-glucaramide (4). Comparison of the reaction pathways from 1 and 5 by H-1 NMR analysis suggests that ring opening of the 1,4-lactone ester (1) and 1,4-lactone amide (7) is faster than ring opening of the corresponding 6,3-lactone ester (5) and 6,3-lactone amide (3). Aminolysis of dimethyl L-tartrate, which cannot form a five-membered lactone, with n-propylamine in DMSO--d(6) was much slower than aminolysis of esterified glucaric acid, indicating that the lactone forming/lactone aminolysis steps are the dominant aminolysis rate enhancing steps from glucarate.

  DOI：

  10.1081/car-120026601

文献信息

• [EN] N-ALKYL-D-GLUCARO-6 AMIDE DERIVATIVES AND ALKYLAMMONIUM SALTS THEREOF AS INTERMEDIATES FOR PREPARING D-GLUCARO-6,3-LACTONE MONOAMIDE<br/>[FR] DÉRIVÉS DE N-ALKYL-D-GLUCARO-6 AMIDE ET SELS D'ALKYLAMMONIUM DE CEUX-CI UTILISÉS EN TANT QU'INTERMÉDIAIRES POUR LA PRÉPARATION DE D-GLUCARO-6,3-LACTONE MONOAMIDE
  申请人：BASF SE

  公开号：WO2019068583A1

  公开（公告）日：2019-04-11

  The presently claimed invention is directed to a process for preparing D-glucaro-6,3-lactone monoamide from D-glucaro-6,3-lactone.

  目前所宣称的发明涉及从D-葡糖醛酸-6,3-内酯制备D-葡糖醛酸-6,3-内酯单酰胺的方法。
• Amphiphilic Amide Derivatives ofD-Glucaric Acid. Synthesis and Complexing Properties Toward Lanthanide(III) Ions
  作者：Sabrina Aury、Patrice Rubini、Christine Gérardin、Claude Selve

  DOI：10.1002/ejoc.200300749

  日期：2004.5

  corresponding amines. The complexing abilities of these compounds toward trivalent lanthanide cations have been studied, using the water-soluble propyl compound, and compared to that of gulonic acid, which corresponds to the complexing part of these molecules. The formation constants of the complexes have been determined and their structures discussed. The surfactant properties of the C8, C10 and C12

  D-葡糖二酸的疏水衍生物 HOOC-(CHOH)4-CONHR，其中 R 是具有 3、8、10 或 12 个碳原子的烷基链，已由 D-glucaro-1,4-内酯和相应的胺。已经使用水溶性丙基化合物研究了这些化合物对三价镧系元素阳离子的络合能力，并与对应于这些分子络合部分的古洛糖酸进行了比较。已经确定了配合物的形成常数并讨论了它们的结构。还评估了 C8、C10 和 C12 葡糖酰胺的表面活性剂特性及其对 LnIII 离子的萃取能力。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• N-alkyl-D-glucaro-6 amide derivatives and alkylammonium salts thereof as intermediates for preparing D-glucaro-6,3-lactone monoamide
  申请人：BASF SE

  公开号：US11208392B2

  公开（公告）日：2021-12-28

  Provided herein is a process for preparing D-glucaro-6,3-lactone monoamide from D-glucaro-6,3-lactone.

  本文提供了一种从 D-葡萄糖-6,3-内酯制备 D-葡萄糖-6,3-内酯单酰胺的工艺。
• Zinner; Fischer, Chemische Berichte, 1956, vol. 89, p. 1503,1506
  作者：Zinner、Fischer

  DOI：——

  日期：——
• Kurtz; Wilson, Journal of Biological Chemistry, 1939, vol. 129, p. 695
  作者：Kurtz、Wilson

  DOI：——

  日期：——