(2S,4S)-2,4-diaminopentanedioic acid | 73464-43-4

• 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: (2S,4S)-2,4-diaminopentanedioic acid
• 英文别名: (2S,4S)-2,4-diaminoglutaric acid；(S,S)-2,4-diaminoglutaric acid；(2S,4S)-4-aminoglutamic acid；4-aminoglutamic acid
• CAS: 73464-43-4
• 化学式: C₅H₁₀N₂O₄
• 分子量: 162.145
• InChiKey: LOPLXECQBMXEBQ-HRFVKAFMSA-N

物化性质

• 沸点：
  391.2±42.0 °C(Predicted)
• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2-di-tert-butyl (2S,4R)-4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylate 在 palladium on activated charcoal ruthenium(IV) oxide 、 lithium hydroxide 、 sodium periodate 、 sodium azide 、 氢气 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 25.0~70.0 ℃ 、303.98 kPa 条件下， 反应 38.5h， 生成 (2S,4S)-2,4-diaminopentanedioic acid
  参考文献：
  名称：

  An efficient and stereospecific synthesis of (2S,4S)-2,4-diaminoglutaric acid

  摘要：

  An efficient and stereospecific synthesis of (2S,4S)-2,4-diaminoglutaric acid 1 starting from trans-4-hydroxy-L-proline 2 is presented. The key step involves the combined application of ruthenium tetroxide (RuO4) oxidation of 4-(tert-butoxycarbonylamino)proline derivatives 7 and 8 followed by regioselective ring opening of the resulting lactams 9 and 10 with 1 M LiOH. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00594-6

文献信息

• Operationally convenient, efficient asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids via methylene dimerization of chiral glycine equivalents with dichloromethane
  作者：Vadim A. Soloshonok、Takeshi Yamada、Hisanori Ueki、Anna M. Moore、Tanner K. Cook、Kelsey L. Arbogast、Anatolii V. Soloshonok、Collin H. Martin、Yasufumi Ohfune

  DOI：10.1016/j.tet.2006.04.023

  日期：2006.6

  This paper presents a practical and efficient asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids using a quite unusual methylene dimerization of chiral nucleophilic glycine equivalents with dichloromethane under phase-transfer catalysis (PTC) conditions. From a synthetic standpoint, the reported procedure is highly operationally convenient and scalable as it does not require any chromatographic

  本文提出了一种实用有效的不对称合成对映体纯的4-氨基谷氨酸的方法，该方法是在相转移催化（PTC）条件下，使用手性亲核甘氨酸当量与二氯甲烷进行非常不寻常的亚甲基二聚。从合成的观点来看，所报道的程序在操作上非常方便且可扩展，因为它不需要对中间产物进行任何色谱纯化。
• Asymmetric Synthesis of All Possible Stereomers of 4‐Aminoglutamic Acid via Michael Condensation of Chiral Ni(II) Complexes of Glycine and Dehydroalanine
  作者：A. S. Saghiyan、A. V. Geolchanyan

  DOI：10.1080/00397910600945951

  日期：2006.12

  4‐aminoglutamic acid. Stereoselectivity of the asymmetric condensation of the complexes exceeded 94%. The condensation of nucleophilic and electrophilic complexes in four possible combinations has resulted in the formation of dimeric complexes of all the stereomers of 4‐aminoglutamic acid: (2S,4S), (2S,4R)‐meso and (2R,4R). Optically active stereomers of 4‐aminoglutamic acid with high optical purity were

  摘要 开发了一种不对称合成 4-氨基谷氨酸所有可能立体异构体的新方法。该方法基于甘氨酸的亲核部分和脱氢丙氨酸的亲电部分在希夫碱与 (S)- 和 (R)-2-N-(N'-苄基脯氨酰) 的手性 Ni(II) 络合物中的不对称迈克尔缩合)氨基二苯甲酮，导致形成 4-氨基谷氨酸的二聚复合物。配合物不对称缩合的立体选择性超过 94%。亲核和亲电复合物以四种可能的组合缩合形成了 4-氨基谷氨酸所有立体异构体的二聚复合物：(2S,4S)、(2S,4R)-meso 和 (2R,4R)。
• Synthesis and piezoelectric properties of N-phthaloylglutamic acid derivatives
  作者：V. O. Ustinova、A. Yu. Vigorov、D. A. Gruzdev、A. S. Nuraeva、I. A. Nizova、E. N. Chulakov、L. Sh. Sadretdinova、P. A. Slepukhin、P. S. Zelenovsky、V. Ya. Shur、V. P. Krasnov

  DOI：10.1007/s11172-017-1905-6

  日期：2017.8

  The (S,S)- and (R,R)-enantiomers of dimethyl 2,4-diphthalimidoglutarate were synthesized by nucleophilic substitution of bromine in dimethyl (2S,4RS)-4-bromo-N-phthaloyl-glutamate upon treatment with potassium phthalimide, followed by separation. The crystal structure of the obtained compounds was studied by X-ray diffraction. Crystals of enantiomerically pure dimethyl 4-hydroxy- and 4-phthalimido

  2,4-二邻苯二甲酰亚胺戊二酸二甲酯的 (S,S)-和 (R,R)-对映异构体是通过溴在 (2S,4RS)-4-溴-N-邻苯二甲酰-谷氨酸二甲酯中用钾处理后的亲核取代而合成的邻苯二甲酰亚胺，然后分离。通过X射线衍射研究了所得化合物的晶体结构。发现对映体纯二甲基 4-羟基-和 4-邻苯二甲酰亚胺-N-邻苯二甲酰谷氨酸盐的晶体具有显着的压电活性。
• Asymmetric synthesis of (2S,4S)-2,4-diaminoglutaric and (2S,3S)-2,3-diamino-2, 3-dimethylsuccinic acids using chiral Ni(II) complexes
  作者：Yu. N. Belokon'、N. I. Chernoglazova、A. S. Batsanov、N. S. Garbalinskaya、V. I. Bakhmutov、Yu. T. Struchkov、V. M. Belikov

  DOI：10.1007/bf00962319

  日期：1987.4
• Asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids via methylenedimerization of chiral glycine equivalents with dichloromethane under operationally convenient conditions
  作者：Stephen M. Taylor、Takeshi Yamada、Hisanori Ueki、Vadim A. Soloshonok

  DOI：10.1016/j.tetlet.2004.10.111

  日期：2004.12

  We found that simple stirring of a biphasic mixture of the Ni(II) complex of glycine Schiff base 2 solution in dichloromethane with 30% aqueous NaOH in the presence of PT catalyst "Bu4N+Br- at room temperature for 24 h results in the formation of diastereo- and enantiornerically pure Ni(II) complex 3, containing (2S,4S) 4-aminoglutamic acid, in high chemical yield. The procedure described in this communication represents a synthetically efficient method for the asymmetric synthesis of 4-aminoglutamic acid on large scale. (C) 2004 Elsevier Ltd. All rights reserved.