(R,S)-4,4,4-trifluoro-2-methylbutanamine hydrochloride | 136564-89-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: (R,S)-4,4,4-trifluoro-2-methylbutanamine hydrochloride
• 英文别名: 4,4,4-trifluoro-2-methylbutan-1-amine hydrochloride；4,4,4-trifluoro-2-methylbutylamine hydrochloride；4,4,4-trifluoro-2-methylbutan-1-amine;hydrochloride
• CAS: 136564-89-1
• 化学式: C₅H₁₀F₃N*ClH
• 分子量: 177.597
• InChiKey: PKZZMNUWBBIRHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,S)-4,4,4-trifluoro-2-methylbutanamine hydrochloride 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 3-Methoxy-4-[6-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-indol-1-ylmethyl]-benzoic acid
  参考文献：
  名称：

  Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of a Series of Fluorinated 3-Benzyl-5-Indolecarboxamides: Identification of 4-[[5-[((2R)-2-Methyl-4,4,4-trifluorobutyl)carbamoyl]-1-methylindol-3-yl]methyl]-3methoxy-N-[(2-methylphenyl)sulfonyl]benzamide, a Potent, Orally Active Antagonist of Leukotrienes D4 and E4

  摘要：

  The continued exploration of a series of 3-(arylmethyl)-1H-indole-5-carboxamides by the introduction of fluorinated amide substituents has resulted in the discovery of 4-[[5-[((2R)-2-methyl-4,4,4-trifluorobutyl)carbamoyl]-1-methylindol-3-yl]methyl]-3-methoxy-N-[(2-methylphenyl)sulfonyl]benzamide (38p, ZENECA ZD 3523),which has been chosen for clinical evaluation. This compound exhibited a K-i of 0.42 nM for displacement of [H-3]LTD(4) on guinea pig lung membranes, a pK(B) Of 10.13 +/- 0.14 versus LTE(4) on guinea pig trachea, and an oral ED(50) Of 1.14 mu mol/kg opposite LTD(4)-induced bronchoconstriction in guinea pigs. The R enantiomer was found to be modestly more potent than the S enantiomer 38o. Modification of the amide substituent to afford achiral compounds was unsuccessful in achieving comparable levels of activity. Profiling of 38p opposite a variety of functional assays has demonstrated the selectivity of this compound as a leukotriene receptor antagonist. The enantioselective synthesis of 38p, which employed a diastereoselective alkylation of (4R,5S)-3-(1-oxo-4,4,4-trifluorobutyl)-4-methyl-5-phenyl-2-oxazolidinone (27) as the key step to establish the chirality of the amide substituent, provided an efficient route for generating 38p in >99% enantiomeric purity.

  DOI：

  10.1021/jm00035a008
• 作为产物：
  描述：

  (R,S)-4,4,4-trifluoro-2-methylbutanamide 在 盐酸 、 sodium sulfate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以79%的产率得到(R,S)-4,4,4-trifluoro-2-methylbutanamine hydrochloride
  参考文献：
  名称：

  Carbamoyl derivatives

  摘要：

  本发明涉及一种新的氨基甲酰衍生物，其化学式为I，该衍生物在此处列出，能拮抗被称为白三烯的花生四烯酸代谢产物的药理作用，使其在需要拮抗这种作用的情况下非常有用，例如在白三烯参与的疾病治疗中，例如在过敏性或炎症性疾病的治疗中，或在内毒素性或创伤性休克症状的治疗中。该发明还提供了含有这些新衍生物的药物组合物，用于进行这种治疗的方法，以及用于制造这些新衍生物的方法和中间体。

  公开号：

  US05286740A1

文献信息

• Indole carbamates as leukotriene antagonists
  申请人：Pfizer Inc

  公开号：US05965745A1

  公开（公告）日：1999-10-12

  Compounds of the formula ##STR1## wherein R.sup.1 AND R.sup.2 are as defined, useful in the treatment of asthma, rheumatoid arthritis, osteoarthritis, bronchitis, chronic obstructive airways diseases, psoriasis, allergic rhinitis, atopic dermatitis, shock, and other inflammatory diseases and for blocking the leucotriene D4 receptor, pharmaceutical compositions containing such compounds and methods of blocking leucotriene D4 receptors using such compositions.

  式##STR1##中R.sup.1和R.sup.2如定义，用于治疗哮喘、类风湿关节炎、骨关节炎、支气管炎、慢性阻塞性气道疾病、牛皮癣、过敏性鼻炎、特应性皮炎、休克和其他炎症性疾病，并用于阻断白三烯D4受体，含有这类化合物的药物组合物以及使用这类组合物阻断白三烯D4受体的方法。
• PHOTOACTIVE COMPOUNDS FOR VAPOR DEPOSITED ORGANIC PHOTOVOLTAIC DEVICES
  申请人：Ubiquitous Energy, Inc.

  公开号：US20220140266A1

  公开（公告）日：2022-05-05

  Photoactive compounds are disclosed. The disclosed compounds can exhibit molecular structural elements tending to increase the evaporability of the compounds, such as by including geometric core disruption by use of conformationally restricted side groups instead of freely rotatable side groups or use of indandione moieties instead of dicyanomethyleneindanone moieties. The disclosed photoactive compounds include those with an imine-bridging linking moiety, which can shift the optical properties to a more red-shifted absorbance as compared to compounds with an alkene-bridging linking moiety. The disclosed photoactive compounds can be used in organic photovoltaic devices, such as visibly transparent or opaque photovoltaic devices.

  本文披露了光致活性化合物。这些化合物具有分子结构元素，倾向于增加化合物的挥发性，例如通过使用构象限制侧基而不是自由旋转的侧基或使用茚酮基团而不是二氰甲基茚酮基团来包括几何核心破坏。披露的光致活性化合物包括具有亚胺桥连连接基团的化合物，可以将光学性质转移至比具有烯烃桥连连接基团的化合物更红移的吸收。披露的光致活性化合物可用于有机光伏器件，例如可见透明或不透明的光伏器件。
• A process for the preparation of 2(R)-methyl-4,4,4-trifluorobutylamine, intermediates, and a process for the preparation of a derivative thereof
  申请人：ZENECA LIMITED

  公开号：EP0489548B1

  公开（公告）日：1994-12-14
• A process for the preparation of a 3-alkylated indole, intermediates, and a process for the preparation of a derivative thereof
  申请人：ZENECA LIMITED

  公开号：EP0489547B1

  公开（公告）日：1998-07-29
• INDOLE CARBAMATES AS LEUKOTRIENE ANTAGONISTS
  申请人：PFIZER INC.

  公开号：EP0863873A1

  公开（公告）日：1998-09-16