(1R,3S)-3-amino-2,2-dimethylcyclobutanecarboxylic acid | 865799-12-8

• 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: (1R,3S)-3-amino-2,2-dimethylcyclobutanecarboxylic acid
• 英文别名: (1R,3S)-3-azaniumyl-2,2-dimethylcyclobutane-1-carboxylate
• CAS: 865799-12-8
• 化学式: C₇H₁₃NO₂
• mdl: MFCD18835297
• 分子量: 143.186
• InChiKey: HEVNTZPOSTVEDU-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3S)-3-amino-2,2-dimethylcyclobutanecarboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以70%的产率得到(1R,3S)-3-amino-2,2-dimethylcyclobutylmethanol
  参考文献：
  名称：

  Synthesis of enantiopure cyclobutane amino acids and amino alcohols

  摘要：

  4-)-(IR,3S)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid and (+)-(IR,3S)-3-amino-2,2-dimethylcyclobutylmethanol, which can be used to prepare enantiopure oligopeptides and cyclobutane-based carbocyclic nucleosides, were synthesized from (+)-(1R)-alpha-pinene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.030
• 作为产物：
  描述：

  (1S,3S)-methyl (3-acetamido-2,2-dimethylcyclobutyl)acetate 在 盐酸 、 ruthenium(IV) oxide 、 sodium periodate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 甲苯 、 乙腈 为溶剂， 反应 53.0h， 生成 (1R,3S)-3-amino-2,2-dimethylcyclobutanecarboxylic acid
  参考文献：
  名称：

  Synthesis of enantiopure cyclobutane amino acids and amino alcohols

  摘要：

  4-)-(IR,3S)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid and (+)-(IR,3S)-3-amino-2,2-dimethylcyclobutylmethanol, which can be used to prepare enantiopure oligopeptides and cyclobutane-based carbocyclic nucleosides, were synthesized from (+)-(1R)-alpha-pinene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.030

文献信息

• Replacement of Thr³² and Gln³⁴ in the <i>C</i>-Terminal Neuropeptide Y Fragment 25–36 by <i>cis</i>-Cyclobutane and <i>cis</i>-Cyclopentane β-Amino Acids Shifts Selectivity toward the Y₄ Receptor
  作者：Łukasz Berlicki、Melanie Kaske、Raquel Gutiérrez-Abad、Günther Bernhardt、Ona Illa、Rosa M. Ortuño、Chiara Cabrele、Armin Buschauer、Oliver Reiser

  DOI：10.1021/jm4008505

  日期：2013.11.14

  Neuropeptide Y (NPY) and pancreatic polypeptide (PP) control central and peripheral processes by activating the G protein coupled receptors YxR (x = 1, 2, 4, 5). We present analogs of the C-terminal fragments 25-36 and 32-36 of NPY and PP containing (1R,2S)-cyclobutane (beta Cbu) or (1R,2S)cyclopentane (beta 6Cpe) fl-amino acids, which display exclusively Y4R affinity. In particular, [beta Cpe(34)]-NPY-(25-36) is a Y4R selective partial agonist (EC50 41 +/- 6 nM, E-max 71%) that binds Y4R with a K-i of 10 +/- 2 nM and a selectivity >100-fold relative to YiR ancrY2R and >50-fold relative to Y5R Comparably, [Y-32, beta Cpe(34)-NPY(PP)-(32-36) selectively binds and activates Y4R (EC50 94 +/- 21 nM, E-max 73%). The NMR structure of [beta Cpe(34)]NPY-(25-36) in dodecylphosphatidylcholine micelles shows a short helix at residues 27-32, while the C-terminal segment R-33 beta Cpe(34)R(35)Y(36) is extended. The biological properties of the,beta Cbu- or beta Cpe-containing NPY and PP C-terminal fragments encourage the future application of these beta-amino acids in the synthesis of selective Y4R ligands.
• AVOTINSH, F. M.;GILIS, A. S.;GUDRINIETSE, EH. YU.;SPINTSE, B. A., IZV. AN LATVSSR. CEP. XIM., 1984, N 3, 339-346
  作者：AVOTINSH, F. M.、GILIS, A. S.、GUDRINIETSE, EH. YU.、SPINTSE, B. A.

  DOI：——

  日期：——
• Synthesis of enantiopure cyclobutane amino acids and amino alcohols
  作者：Carmen Balo、Olga Caamaño、Franco Fernández、Carmen López

  DOI：10.1016/j.tetasy.2005.06.030

  日期：2005.8

  4-)-(IR,3S)-3-Amino-2,2-dimethylcyclobutanecarboxylic acid and (+)-(IR,3S)-3-amino-2,2-dimethylcyclobutylmethanol, which can be used to prepare enantiopure oligopeptides and cyclobutane-based carbocyclic nucleosides, were synthesized from (+)-(1R)-alpha-pinene. (c) 2005 Elsevier Ltd. All rights reserved.