(S)-1-cyclopropyl-2-methoxyethanamine | 1173690-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-cyclopropyl-2-methoxyethanamine
• 英文别名: (1S)-1-cyclopropyl-2-methoxyethan-1-amine；(1S)-1-cyclopropyl-2-methoxyethanamine
• CAS: 1173690-15-7
• 化学式: C₆H₁₃NO
• 分子量: 115.175
• InChiKey: APFVIOCNPBAUSZ-ZCFIWIBFSA-N

物化性质

• 沸点：
  161.6±13.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-cyclopropyl-2-methoxyethanamine 在 甲醇 、 sodium tetrahydroborate 、 sodium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 (S)-1-cyclopropyl-2-methoxy-N-((5-(trifluoromethyl)pyridin-2-yl)methyl)ethanamine
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS OF USE
  [FR] COMPOSÉS ET PROCÉDÉS D'UTILISATION

  摘要：

  提供了式(A)化合物：式（A）；及其药学上可接受的盐，以及其药物组合物、制备工艺和处理方法；其中 Ra、Ra'、环 A、环 B 和 R1 如本文所述的任一实施方案中所定义。

  公开号：

  WO2023146987A1
• 作为产物：
  描述：

  癸酸乙酯 、 1-环丙基-2-甲氧基乙胺 在 Candida antarctica B lipase 作用下， 以 甲基叔丁基醚 为溶剂， 反应 120.0h， 以35%的产率得到(S)-1-cyclopropyl-2-methoxyethanamine
  参考文献：
  名称：

  Preparation of (S)-1-Cyclopropyl-2-methoxyethanamine by a Chemoenzymatic Route Using Leucine Dehydrogenase

  摘要：

  (S)-1-Cyclopropyl-2-methoxyethanamine is a key chiral intermediate for the synthesis of a corticotropin-releasing factor-1(CRF-1) receptor antagonist. Resolution of the racemic amine by transaminase from Vibrio fluvalis gave a 38% yield of the S-amine with 53% ee. Resolution by lipase-catalyzed acylation provided the S-amine in 35% yield with 91% ee. With limited success of these resolution approaches, an efficient chemo-enzymatic route to (S)-1-cyclopropyl-2-methoxyethanamine was devised starting from methylcyclopropyl ketone. Permanganate oxidation of the ketone gave cyclopropylglyoxylic acid, which was converted to (S)-cyclopropylglycine by reductive amination using leucine dehydrogenase from Thermoactinomyces intermedius with NADH cofactor recycling by formate dehydrogenase from Pichia pastoris. Both enzymes were cloned and expressed in recombinant E. coli. (S)-Cyclopropylglycine obtained from enzymatic reductive amination was isolated as the N-Boc derivative and converted to the desired amine by reduction, methylation, and deprotection to give (S)1-cyclopropyl-2-methoxyethanamine in 62% overall yield from cyclopropylglyoxylic acid, with no detectable R-enantiomer.

  DOI：

  10.1021/op2003562

文献信息

• Pyrazinone Modulator of Corticotropin-Releasing Factor Receptor Activity
  申请人：Hartz Richard A.

  公开号：US20100029684A1

  公开（公告）日：2010-02-04

  The invention relates to the compound (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-(6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylamino)-5-oxo-4,5-dihydropyrazine-2-carbonitrile, pharmaceutical compositions of the compound, and methods of using the compound for the treatment of psychiatric disorders and neurological diseases including depression, anxiety related disorders, irritable bowel syndrome, addiction and negative aspects of drug and alcohol withdrawal, and other conditions associated with CRF.

  这项发明涉及化合物(S)-4-(1-环丙基-2-甲氧基乙基)-6-(6-(二氟甲氧基)-2,5-二甲基吡啶-3-基氨基)-5-氧代-4,5-二氢吡嗪-2-羰基腈，该化合物的药物组合物，以及使用该化合物治疗精神障碍和神经系统疾病，包括抑郁症、焦虑相关障碍、肠易激综合征、成瘾以及药物和酒精戒断的负面影响，以及与CRF相关的其他症状的方法。
• PYRAZINONE MODULATOR OF CORTICOTROPIN-RELEASING FACTOR RECEPTOR ACTIVITY
  申请人：Bristol-Myers Squibb Company

  公开号：EP2303867B1

  公开（公告）日：2014-12-17
• US7932256B2
  申请人：——

  公开号：US7932256B2

  公开（公告）日：2011-04-26
• [EN] STEREOSELECTIVE RESOLUTION OF RACEMIC AMINES<br/>[FR] RÉSOLUTION STÉRÉO-SÉLECTIVE D'AMINES RACÉMIQUES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2009006492A2

  公开（公告）日：2009-01-08

  The invention relates to processes for the enzymatic, stereoselective resolution of racemic amines to provide chiral amines.
• [EN] PYRAZINONE MODULATOR OF CORTICOTROPIN-RELEASING FACTOR RECEPTOR ACTIVITY<br/>[FR] MODULATEUR PYRAZINONE DE L'ACTIVITÉ DE LA CORTICOLIBÉRINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010014280A1

  公开（公告）日：2010-02-04

  The invention relates to the compound (S)~4»(l-cyclopropyl-2-methoxyethyl)- 6-(6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylatnino)-5-oxo-4,5-dihydropyrazine- 2-carbonitrile, pharmaceutical compositions of the compound, and methods of using the compound for the treatment of psychiatric disorders and neurological diseases including depression, anxiety related disorders, irritable bowel syndrome, addiction and negative aspects of drug and alcohol withdrawal, and other conditions associated with CRF.