(2R,4R)-2,4-吡咯烷二甲酸 | 130830-78-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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
• 中文名称: (2R,4R)-2,4-吡咯烷二甲酸
• 英文名称: (2R,4R)-2,4-pyrrolidinedicarboxylic acid
• 英文别名: (2R,4R)-4-(2-methylethenyl)-2-carboxypyrrolidine；cis-4-carboxy-D-proline；D-cis-2,4-PDC；(2R,4R)-pyrrolidine-2,4-dicarboxylic acid
• CAS: 130830-78-3
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: NRSBQSJHFYZIPH-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-cis-4-carboxy-D-proline dimethyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.33h， 生成 (2R,4R)-2,4-吡咯烷二甲酸
  参考文献：
  名称：

  Conformationally defined neurotransmitter analogs. Selective inhibition of glutamate uptake by one pyrrolidine-2,4-dicarboxylate diastereomer

  摘要：

  In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared. These ''conformer mimics'', the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of [H-3]-L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites. While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport. These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.

  DOI：

  10.1021/jm00106a037

文献信息

• An enantioselective route to pyrrolidines: removal of the chiral template from homochiral pyrroloimidazoles
  作者：Raymond C.F. Jones、Kevin J. Howard、John S. Snaith、Alexander J. Blake、Wang-Shei Li、Peter J. Steel

  DOI：10.1016/j.tet.2011.08.099

  日期：2011.11

  Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral 4,5-dihydroimidazolium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g., naturally occurring and other optically active proline derivatives, and optically active pyrrolizidines and indolizidines

  从旋光的吡咯并咪唑类化合物中进行两步还原性去除，可以从均手性的4，5-二氢咪唑鎓内酯的1，3-偶极环加成中获得旋光性的取代的吡咯烷。取代基的选择性操纵提供了例如天然存在的和其他光学活性的脯氨酸衍生物，以及光学活性的吡咯烷核苷和吲哚并核苷。
• Asymmetric synthesis of α-amino acids via cationic aza-cope rearrangements
  作者：Claude Agami、François Couty、Jing Lin、Axelle Mikaeloff、Michel Poursoulis

  DOI：10.1016/s0040-4020(01)87201-x

  日期：1993.8

  Ene-iminium intermediates resulting from reaction between glyoxal and β-amino alcohols rearrange by an aza-Cope process. Three different tandem reactions are thus carried out; their first component is this cationic rearrangement, the second step being either an iminium hydrolysis, a nucleophile-induced ene-iminium cyclization or a Mannich reaction. The last two sequences lead to homochiral proline

  由乙二醛和β-氨基醇之间的反应产生的乙炔亚胺中间体通过aza-Cope工艺重排。因此进行了三种不同的串联反应。它们的第一个成分是阳离子重排，第二个步骤是亚胺水解，亲核试剂诱导的烯-亚胺环化或曼尼希反应。最后两个序列导致同手性脯氨酸衍生物。
• Stereospecific Synthesis of cis-2,4-Pyrrolidinedicarboxylic Acid and cis-2,5-Piperidinedicarboxylic Acid.
  作者：Yasushi ARAKAWA、Mika YASUDA、Masafumi OHNISHI、Shigeyuki YOSHIFUJI

  DOI：10.1248/cpb.45.255

  日期：——

  Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2, 4-pyrrolidinedicarboxylic acid and cis-2, 5-piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S, 4S)-(-)-2, 4-pyrrolidinedicarboxylic acid and (2R, 4R)-(+)-2, 4-pyrrolidinedicarboxylic acid were synthesized from (1S, 4R)-(+)-2-azabicyclo[2.2.1]hept-5-en-3-one and (1R, 4S)-(-)-2-azabicyclo[2.2.1]hept-5-en-3-one, respectively.

  来自杂环Diels-Alder加合物的内酰胺通过钌四氧化物氧化被立体特异性地转化为顺-2, 4-吡咯烷二羧酸和顺-2, 5-哌啶二羧酸。光学活性的（2S, 4S）-(-)-2, 4-吡咯烷二羧酸和（2R, 4R）-(+)-2, 4-吡咯烷二羧酸分别是从（1S, 4R）-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮和（1R, 4S）-(-)-2-氮杂双环[2.2.1]庚-5-烯-3-酮合成的。
• BRIDGES, RICHARD J.;STANLEY, MARK S.;ANDERSON, MICHAEL W.;COTMAN, CARL W.+, J. MED. CHEM., 34,(1991) N, C. 717-725
  作者：BRIDGES, RICHARD J.、STANLEY, MARK S.、ANDERSON, MICHAEL W.、COTMAN, CARL W.+

  DOI：——

  日期：——
• METHOD OF INHIBITING THE TRANSPORT OF L-GLUTAMATE
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0497895A1

  公开（公告）日：1992-08-12