(R)-3-Methyl-1-(phenylmethyl)piperazin-2-one | 170033-55-3

• 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: (R)-3-Methyl-1-(phenylmethyl)piperazin-2-one
• 英文别名: 1-Benzyl-(3R)-methylpiperazine-2-one；(3R)-1-benzyl-3-methylpiperazin-2-one
• CAS: 170033-55-3
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: RTJNLSJXASYVHM-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-Methyl-1-(phenylmethyl)piperazin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (R)-1-苄基-3-甲基哌嗪
  参考文献：
  名称：

  Asymmetric Synthesis of 2,6-Methylated Piperazines

  摘要：

  The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step. The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intramolecular Mitsunobu reaction to set the required stereochemistry. The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6-trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction. These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.

  DOI：

  10.1021/jo00118a039
• 作为产物：
  描述：

  N-苄基乙醇胺 在 三苯基膦 、 N,N'-羰基二咪唑 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 34.75h， 生成 (R)-3-Methyl-1-(phenylmethyl)piperazin-2-one
  参考文献：
  名称：

  Asymmetric Synthesis of 2,6-Methylated Piperazines

  摘要：

  The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step. The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intramolecular Mitsunobu reaction to set the required stereochemistry. The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6-trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction. These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.

  DOI：

  10.1021/jo00118a039

文献信息

• Imidazo[1,5-A]quinolines for treatment of anxiety and sleep disorders
  申请人：The Upjohn Company

  公开号：US05594140A1

  公开（公告）日：1997-01-14

  Imidazo[1,5-a]quinolines of formula (I) which are useful pharmaceutical agents for the treatment of anxiety, sleep disorders, panic states, convulsions and muscle disorders. ##STR1##

  化学式为(I)的咪唑并[1,5-a]喹啉是治疗焦虑、睡眠障碍、惊恐状态、癫痫和肌肉疾病的有用药物。##STR1##
• Use of imidazo\x9b1,5-a!quinolones as neuroprotective agents
  申请人：Pharmacia & Upjohn Company

  公开号：US05935970A1

  公开（公告）日：1999-08-10

  The imidazo\x9b1,5-a!quinolines (I) are useful in treating neurological diseases/conditions or chronic neurodegenerative diseases/conditions.

  咪唑[1,5-a]喹啉（I）在治疗神经疾病/症或慢性神经退行性疾病/症方面具有用处。
• Asymmetric Synthesis of 2,6-Methylated Piperazines
  作者：John W. Mickelson、Kenneth L. Belonga、E. Jon Jacobsen

  DOI：10.1021/jo00118a039

  日期：1995.6

  The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step. The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intramolecular Mitsunobu reaction to set the required stereochemistry. The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6-trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction. These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.