(1R,2R)-2-[[(S)-1-苯基乙基]氨基]环戊甲酸乙酯 | 359586-67-7

• 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: (1R,2R)-2-[[(S)-1-苯基乙基]氨基]环戊甲酸乙酯
• 英文名称: ethyl (1R,2R)-2-[(1'S)-phenylethyl]aminocyclopentane-1-carboxylate
• 英文别名: Ethyl (1R,2R)-2-[[(S)-1-Phenylethyl]amino]cyclopentanecarboxylate；ethyl (1R,2R)-2-[[(1S)-1-phenylethyl]amino]cyclopentane-1-carboxylate
• CAS: 359586-67-7
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: XFESHQNKLZLTHP-NWANDNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 (1R,2R)-2-[[(S)-1-苯基乙基]氨基]环戊甲酸乙酯
  参考文献：
  名称：

  (S,S)-trans-Cyclopentane-Constrained Peptide Nucleic Acids. A General Backbone Modification that Improves Binding Affinity and Sequence Specificity

  摘要：

  Replacing the ethylenediamine portion of aminoethylglycine peptide nucleic acids (aegPNAs) with one or more (S,S)-trans-cyclopentane diamine units significantly increases binding affinity and sequence specificity to complementary DNA, making these modified PNAs ideal for use as nucleic acid probes in genomic analysis. The synthesis and study of this new class of PNAs (tcypPNAs) is described in which trans-cyclopentane diamine has been incorporated into several positions, and in varying number, within PNA backbones of mixed-base sequences.

  DOI：

  10.1021/ja046280q

文献信息

• Optimized stereoselective and scalable synthesis of five‐membered cyclic <i>trans</i>‐β‐amino acid building blocks via reductive amination
  作者：Jungwoo Hong、Wonchul Lee、Hee‐Seung Lee

  DOI：10.1002/bkcs.12786

  日期：2023.12

  We present an optimized method for the stereoselective synthesis of five-membered alicyclic and heterocyclic trans-β-amino acid derivatives. The process involves a reductive amination of β-keto esters using chiral auxiliary amines, with formic acid acting as a facilitator for rapid, diastereoselective reductions under gentle conditions. Our approach notably enhances isolated yields and permits the

  我们提出了一种立体选择性合成五元脂环族和杂环反式-β-氨基酸衍生物的优化方法。该过程涉及使用手性辅助胺对 β-酮酯进行还原胺化，并以甲酸作为促进剂，在温和条件下实现快速、非对映选择性还原。我们的方法显着提高了分离产率，并允许大规模生产反式-2-氨基环戊烷甲酸（反式-ACPC）、4-氨基吡咯烷-3-甲酸（反式-APC）、4-氨基四氢呋喃-3-甲酸（反式-ATFC） ）和4-氨基四氢噻吩-3-羧酸（反式-ATTC）结构单元。
• An Efficient Route to Either Enantiomer of <i>trans</i>-2-Aminocyclopentanecarboxylic Acid
  作者：Paul R. LePlae、Naoki Umezawa、Hee-Seung Lee、Samuel H. Gellman

  DOI：10.1021/jo010279h

  日期：2001.8.1
• (<i>S</i>,<i>S</i>)-<i>trans-</i>Cyclopentane-Constrained Peptide Nucleic Acids. A General Backbone Modification that Improves Binding Affinity and Sequence Specificity
  作者：Jonathan K. Pokorski、Mark A. Witschi、Bethany L. Purnell、Daniel H. Appella

  DOI：10.1021/ja046280q

  日期：2004.11.1

  Replacing the ethylenediamine portion of aminoethylglycine peptide nucleic acids (aegPNAs) with one or more (S,S)-trans-cyclopentane diamine units significantly increases binding affinity and sequence specificity to complementary DNA, making these modified PNAs ideal for use as nucleic acid probes in genomic analysis. The synthesis and study of this new class of PNAs (tcypPNAs) is described in which trans-cyclopentane diamine has been incorporated into several positions, and in varying number, within PNA backbones of mixed-base sequences.