(αR,1R,2S)-2-methyl-1-(1-phenylethylamino)cyclobutanecarboxamide | 530102-43-3

• 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: (αR,1R,2S)-2-methyl-1-(1-phenylethylamino)cyclobutanecarboxamide
• 英文别名: (1R,2S)-2-methyl-1-[[(1R)-1-phenylethyl]amino]cyclobutane-1-carboxamide
• CAS: 530102-43-3
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: PZDVOTIDJACBNT-MISXGVKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (αR,1R,2S)-2-methyl-1-(1-phenylethylamino)cyclobutanecarboxamide 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (1R,2S)-1-amino-2-methylcyclobutanecarboxamide hydrochloride
  参考文献：
  名称：

  Cyclobutane amino acids (CBAAs): asymmetric Strecker synthesis of enantiopure cis- and trans-2,4-methanovalines

  摘要：

  Synthesis of enantiopure 2.4-methanovalines has been achieved by means of asymmetric Strecker synthesis starting from racemic 2-methylcyclobutanone. The trans-configured alpha-amino acids were obtained from cyanide additions carried out in methanol, whereas the cis-configured 2,4-methatiovalines were accessible via reactions in hexane. Relative stereochemistry was elucidated from NOESY experiments, while absolute configurations were assigned from X-ray crystallographic analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00868-6
• 作为产物：
  描述：

  2alpha-甲基环丁酮 在 硫酸 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 111.0h， 生成 (αR,1R,2S)-2-methyl-1-(1-phenylethylamino)cyclobutanecarboxamide
  参考文献：
  名称：

  Cyclobutane amino acids (CBAAs): asymmetric Strecker synthesis of enantiopure cis- and trans-2,4-methanovalines

  摘要：

  Synthesis of enantiopure 2.4-methanovalines has been achieved by means of asymmetric Strecker synthesis starting from racemic 2-methylcyclobutanone. The trans-configured alpha-amino acids were obtained from cyanide additions carried out in methanol, whereas the cis-configured 2,4-methatiovalines were accessible via reactions in hexane. Relative stereochemistry was elucidated from NOESY experiments, while absolute configurations were assigned from X-ray crystallographic analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00868-6

文献信息

• Cyclobutane amino acids (CBAAs): asymmetric Strecker synthesis of enantiopure cis- and trans-2,4-methanovalines
  作者：Franz-J. Volk、Marita Wagner、August W. Frahm

  DOI：10.1016/s0957-4166(02)00868-6

  日期：2003.2

  Synthesis of enantiopure 2.4-methanovalines has been achieved by means of asymmetric Strecker synthesis starting from racemic 2-methylcyclobutanone. The trans-configured alpha-amino acids were obtained from cyanide additions carried out in methanol, whereas the cis-configured 2,4-methatiovalines were accessible via reactions in hexane. Relative stereochemistry was elucidated from NOESY experiments, while absolute configurations were assigned from X-ray crystallographic analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.