(S)-2-methyl-azetidine-1,2-dicarboxylic acid 1-benzyl ester | 942203-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-methyl-azetidine-1,2-dicarboxylic acid 1-benzyl ester
• 英文别名: (2S)-2-methyl-1-phenylmethoxycarbonylazetidine-2-carboxylic acid
• CAS: 942203-02-3
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: KVJTUZMRAXZYDZ-ZDUSSCGKSA-N

物化性质

• 沸点：
  414.9±45.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-methyl-azetidine-1,2-dicarboxylic acid 1-benzyl ester 在 palladium on activated charcoal 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 生成 (2S)-1-acetyl-2-methyl-N-[(2S)-1-(methylamino)-1-oxopropan-2-yl]azetidine-2-carboxamide
  参考文献：
  名称：

  2-Alkyl-2-carboxy-azetidines as scaffolds for the induction of γ-turns

  摘要：

  To investigate the ability of 2-alkyl-2-carboxy-azetidines (Azx) to induce reverse turns when incorporated into peptides, RCO-Azx-L-A1a-NHMe dipeptide derivatives were selected as simplified tetrapeptide models, in which the azetidine residue is incorporated at the i + 1 position. Molecular modelling, H-1 NMR and FTIR studies showed the high tendency of the model tetrapeptides to adopt gamma-turn conformations, indicating that these azetidine-containing amino acids could serve as general gamma-turn promoters. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.126
• 作为产物：
  描述：

  Tert-butyl 2-[benzyl(2-chloroethyl)amino]propanoate 在 盐酸 、 硫酸 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 水 、 氢气 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 (S)-2-methyl-azetidine-1,2-dicarboxylic acid 1-benzyl ester
  参考文献：
  名称：

  Practical preparation of enantiopure 2-methyl-azetidine-2-carboxylic acid; a γ-turn promoter

  摘要：

  A robust and practical synthesis of each enantiomer of 2-methyl-azetidine-2-carboxylic acid, based on the use of (S)-phenylglycinol as resolving agent, is described. This synthesis affords practical quantities of this quaternary amino acid suitably N- and C-protected for use in further peptide coupling. Synthetic highlights include the formation of the azetidine ring by intramolecular alkylation and the facile separation of the diastereoisomeric amides derived from phenylglycinol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.006

文献信息

• US6544976B1
  申请人：——

  公开号：US6544976B1

  公开（公告）日：2003-04-08
• [EN] NEUROTROPHIC 2-AZETIDINECARBOXYLIC ACID DERIVATIVES, AND RELATED COMPOSITIONS AND METHODS<br/>[FR] DERIVES NEUROTROPHIQUES D'ACIDE 2-AZETIDINECARBOXYLIQUE, ET COMPOSITIONS ET METHODES Y RELATIVES
  申请人：ORTHO MCNEIL PHARM INC

  公开号：WO2001004091A1

  公开（公告）日：2001-01-18

  Compounds having general structure (a) wherein R1 is selected from the group consisting of COCOR?2, CONHR3, SO¿2R4 and (b). X and Y are (i) C=O and (ii) O or NR5, Z is (C¿1?-C5)-straight or branched alkyl or alkenyl substituted in one or more positions with Ar, which Ar is selected from the group consisting of 2-pyridyl, 3-pyridyl, 4-pyridyl, phenyl and substituted phenyl. A ix X-Y-Z or hydrogen, pharmaceutical compositions comprising same and methods of using these compsositions to treat and prevent disorders characterized by neuronal damage.