2-(difluoromethyl)phenylalanine | 105743-54-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-(difluoromethyl)phenylalanine
• 英文别名: α-Difluormethylphenylalanin；D-Phenylalanine, I+/--(difluoromethyl)-；2-amino-2-benzyl-3,3-difluoropropanoic acid
• CAS: 105743-54-2
• 化学式: C₁₀H₁₁F₂NO₂
• 分子量: 215.2
• InChiKey: WDMZLTTVVYDAHH-UHFFFAOYSA-N

物化性质

• 沸点：
  347.2±42.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-(benzylideneamino)-3-phenylpropionate 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-(difluoromethyl)phenylalanine
  参考文献：
  名称：

  Direct synthesis of .alpha.-halogenomethyl-.alpha.-amino acids from the parent .alpha.-amino acids

  摘要：

  DOI：

  10.1021/jo01329a029

文献信息

• [EN] TRIAZINES DERIVATIVES AS CELL ADHESION INHIBITORS<br/>[FR] DERIVES DE TRIAZINES COMME INHIBITEURS DE L'ADHESION CELLULAIRE
  申请人：RANBAXY LAB LTD

  公开号：WO2005030735A1

  公开（公告）日：2005-04-07

  The present invention relates to triazine derivatives as cell adhesion inhibitors. The compounds of this invention can be useful inter alia, for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies, including inflammatory and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type I diabetes, multiple sclerosis, allograft rejection, psoriasis. The compounds can be used to formulate pharmacological compositions, and the methods of treating bronchial asthma, rheumatoid arthritis, multiple sclerosis, type I diabetes, psoriasis, allograft rejection, and other inflammatory and/or autoimmune disorders, using the compounds are also provided herein.

  本发明涉及三嗪衍生物作为细胞黏附抑制剂。本发明的化合物可以用于抑制和预防细胞黏附和细胞黏附介导的病理反应，包括支气管哮喘、类风湿性关节炎、1型糖尿病、多发性硬化症、移植排斥、牛皮癣等炎性和自身免疫性疾病。这些化合物可以用于制备药物组合物，并且本文还提供了使用这些化合物治疗支气管哮喘、类风湿性关节炎、多发性硬化症、1型糖尿病、牛皮癣、移植排斥和其他炎性和/或自身免疫性疾病的方法。
• A New Strategy for the Synthesis of α-Difluoromethyl-Substituted α-Hydroxy and α-Amino Acids
  作者：Sergey N. Osipov、Alexander S. Golubev、Norbert Sewald、Thomas Michel、Alexey F. Kolomiets、Alexander V. Fokin、Klaus Burger

  DOI：10.1021/jo9608331

  日期：1996.1.1

  A new method for the preparation of alpha-chlorodifluoromethyl-, alpha-bromodifluoromethyl-, and alpha-difluoromethyl-substituted alpha-hydroxy and alpha-amino acid esters 11, 19-21 is described. The key step of the synthesis is the regioselective alkylation of ketones 5, 7-9 and imines 16-18 with C-nucleophiles. The ketones 7-9 are readily available from 3,3,3-trifluorolactate 1 by a five-step procedure

  描述了一种制备α-氯二氟甲基，α-溴二氟甲基和α-二氟甲基取代的α-羟基和α-氨基酸酯11、19-21的新方法。合成的关键步骤是用C-亲核试剂对酮5、7-9和亚胺16-18进行区域选择性烷基化。酮7-9可通过五步法容易地从3,3,3-三氟乳酸酯1获得。随后从19-21除去保护基团提供相应的游离氨基酸25、26、28。
• Amine-based and amide-based inhibitors of semicarbazide-sensitive amine oxidase (SSAO) enzyne activity and VAP-1 mediated adhesion useful for treatment of diseases
  申请人：Salter-Cid M. Luisa

  公开号：US20060025438A1

  公开（公告）日：2006-02-02

  Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.

  本发明揭示了一种抑制半卡巴肼敏感性胺基氧化酶（SSAO）的化合物和方法，SSAO也被称为血管黏附蛋白-1（VAP-1）。所揭示的化合物为含有胺基和酰胺基的化合物。这些化合物和组合物对于治疗炎症、炎症性疾病和自身免疫性疾病等疾病是有用的。
• Amine-based and amide-based inhibitors of semicarbazide-sensitive amine oxidase (SSAO)enzyme activity and VAP-1 mediated adhesion useful for treatment of diseases
  申请人：Salter-Cid M. Luisa

  公开号：US20070078157A1

  公开（公告）日：2007-04-05

  Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.

  本发明公开了抑制半卡巴肼敏感性胺氧化酶（SSAO），也称为血管黏附蛋白-1（VAP-1）的组合物和方法。所公开的化合物是含有胺基和酰胺基的化合物。这些化合物和组合物可用于治疗炎症、炎症性疾病和自身免疫性疾病等疾病。
• AMINE-BASED AND AMIDE-BASED INHIBITORS OF SEMICARBAZIDE-SENSITIVE AMINE OXIDASE (SSAO) ENZYME ACTIVITY AND VAP-1 MEDIATED ADHESION USEFUL FOR TREATMENT OF DISEASES
  申请人：SALTER-CID LUISA M.

  公开号：US20120172392A1

  公开（公告）日：2012-07-05

  Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.

  本文揭示了一种抑制半卡巴肼敏感性胺氧化酶（SSAO），也称为血管粘附蛋白-1（VAP-1）的组合物和方法。所揭示的化合物包括含胺和含酰胺的化合物。这些化合物和组合物对于治疗疾病，包括炎症、炎症性疾病和自身免疫性疾病非常有用。

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