N,N-dibenzylasparaginic acid dibenzyl ester | 159497-65-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-dibenzylasparaginic acid dibenzyl ester
• 英文别名: N,N-dibenzyl-L-aspartic acid dibenzyl ester；dibenzyl N,N-dibenzylaspartate；dibenzyl (2S)-2-(dibenzylamino)butanedioate
• CAS: 159497-65-1
• 化学式: C₃₂H₃₁NO₄
• 分子量: 493.602
• InChiKey: SIUKCNKSBCNLAT-PMERELPUSA-N

物化性质

• 沸点：
  619.2±55.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-dibenzylasparaginic acid dibenzyl ester 在 palladium dihydroxide 盐酸 、 lithium aluminium tetrahydride 、 氯化亚砜 、 水 、 氢气 、 氰化四丁基铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， -50.0~65.0 ℃ 、101.01 kPa 条件下， 反应 91.33h， 生成 methyl (S)-(+)-1-(phenylmethyl)-3-pyrrolidinecarboxylate
  参考文献：
  名称：

  A Practical Ex-Chiral-Pool Synthesis of β-Proline and Homo-β-Proline

  摘要：

  DOI：

  10.1055/s-1998-2185
• 作为产物：
  描述：

  L-天门冬氨酸 、 溴甲苯 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 以77%的产率得到N,N-dibenzylasparaginic acid dibenzyl ester
  参考文献：
  名称：

  实用的EPC合成1,2-和1,3-氨基醇

  摘要：

  据报道，通过从L-天冬氨酸获得的关键中间体2和8a，b有效合成了对映体纯的1，2-和1，3-氨基醇（4，10）。以4d为例，表明该产品可以用作不寻常的氨基醛和非蛋白氨基酸的前体。

  DOI：

  10.1016/s0040-4039(00)79340-3

文献信息

• Enantio- and diastereocontrolled dopamine D1, D2, D3 and D4 receptor binding of N-(3-pyrrolidinylmethyl)benzamides synthesized from aspartic acid
  作者：Christoph Thomas、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(99)00086-4

  日期：1999.3

  N-(3-pyrrolidinyl)benzamides leading to the selective dopamine D3 ligand ent1h and the derivatives 1g and 1e/ent1e which preferably recognize human D2 or D4 receptors, respectively, is described. Binding profiles were controlled by both, absolute and relative configuration. The enantiopure target compounds were synthesized from aspartic acid.

  描述了N-（3-吡咯烷基）苯甲酰胺的亚受体选择性调节，导致选择性的多巴胺D3配体ent1h以及优选分别识别人D2或D4受体的衍生物1g和1e / ent1e。结合概况由绝对和相对构型两者控制。对映体纯的目标化合物由天冬氨酸合成。
• Isolation and structural elucidation of callipeltins J–M: antifungal peptides from the marine sponge Latrunculia sp.
  作者：Maria Valeria D'Auria、Valentina Sepe、Rosa D'Orsi、Filomena Bellotta、Cécile Debitus、Angela Zampella

  DOI：10.1016/j.tet.2006.10.032

  日期：2007.1

  Continued investigation of the polar extracts of the marine sponge Latrunculia sp. has resulted in the discovery of callipeltins J–M. The new structures were determined by interpretation of their NMR and MS data. The stereochemistry of the unusual 3-methylglutamine residue in callipeltins J and K was secured by stereoselective synthesis and Marfey's LC–MS analysis.

  继续研究海洋海绵Latrunculia sp。的极性提取物。已经导致发现卡培尔丁J–M。通过解释其NMR和MS数据确定新结构。立体选择性合成和Marfey的LC-MS分析确保了愈伤组织J和K中不常见的3-甲基谷氨酰胺残基的立体化学。
• Guarnieri, Walter; Grehl, Matthias; Hoppe, Dieter, Angewandte Chemie, 1994, vol. 106, # 17, p. 1815 - 1818
  作者：Guarnieri, Walter、Grehl, Matthias、Hoppe, Dieter

  DOI：——

  日期：——
• Regio- and Stereoselective Lithiation and C-Substitution of (S)-2-(Dibenzylamino)butane-1,4-diol via Dicarbamates
  作者：Walter Guarnieri、Martin Sendzik、Roland Fröhlich、Dieter Hoppe

  DOI：10.1055/s-1998-6099

  日期：1998.9
• Enantiomerically Pure Amino Alcohols and Diamino Alcohols from L-Aspartic Acid. Application to the Synthesis of Epi- and Diepislaframine
  作者：Peter Gmeiner、Dagmar Junge、Annerose Kaertner

  DOI：10.1021/jo00101a042

  日期：1994.11

  Starting from natural aspartic acid (6) a practical method for the synthesis of enantiomerically pure 3-amino alcohols 8 including 3,4-diamino derivatives is described. After perbenzylation of 6 and reduction of both carboxylates, position 4 of the resultant (dibenzylamino)butanediol (11) could be regioselectively blocked to afford the silyloxy-protected intermediate 12a. Functionalization of position 1 was accomplished by nucleophilic displacement reactions including a 2-fold migration of the dibenzylamino substituent or by reductive amination of the amino aldehyde 15. Both routes proceeded under complete preservation of the optical purity. For envisioned SAR studies, we, furthermore, report on the application of this method to a chirospecific synthesis of epi- and diepislaframine (9a and 9b) as diastereomers of the highly bioactive indolizidine alkaloid slaframine (9c). Our first approach including reductive coupling of the chiral amino aldehyde 15 with 5-hydroxypyrrolidine failed when formation of a quaternary ammonium salt occurred, preventing the anticipated anionic cyclization. Therefore, we turned out attention to methodology developed by Wasserman. In fact, introduction of a 3-hydroxypyrrole-2-carboxylate fragment gave a cyclization precursor (30b) which could be successfully transformed into epi- and diepislaframine.