2-methyl-4,4,4-trifluorobutyryl chloride | 136564-78-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 2-methyl-4,4,4-trifluorobutyryl chloride
• 英文别名: 4,4,4-trifluoro-2-methylbutanoyl chloride
• CAS: 136564-78-8
• 化学式: C₅H₆ClF₃O
• mdl: MFCD18641894
• 分子量: 174.55
• InChiKey: KJGTUKSHPIVAPB-UHFFFAOYSA-N

物化性质

• 沸点：
  106.8±35.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  2-methyl-4,4,4-trifluorobutyryl chloride 在 三氯化铝 、 potassium tert-butylate 、 氧气 、 间氯过氧苯甲酸 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(R)-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-4.4,4-trifluoro-1-butanone
  参考文献：
  名称：

  Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile

  摘要：

  The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00739-4
• 作为产物：
  描述：

  2-甲基-4,4,4-三氟丁酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 2-methyl-4,4,4-trifluorobutyryl chloride
  参考文献：
  名称：

  配体促进的 C(sp3)–H 和 C(sp2)–H 键的烷基化

  摘要：

  9-甲基吖啶被确定为一种普遍有效的配体，可促进 Pd(II) 催化的 C(sp3)-H 和 C(sp2)-H 与各种烷基碘的简单酰胺的烷基化。这种烷基化反应用于制备非天然氨基酸和几何控制的三和四取代丙烯酸。

  DOI：

  10.1021/ja508165a

文献信息

• Developing Pd(II) Catalyzed Double sp³ C–H Alkoxylation for Synthesis of Symmetric and Unsymmetric Acetals
  作者：Yu Zong、Yu Rao

  DOI：10.1021/ol502377x

  日期：2014.10.17

  effective Pd(II) catalyzed double unactivated C(sp3)–H alkoxylation has been developed to prepare both symmetric and unsymmetric acetals. This new reaction demonstrates good functional group tolerance, excellent reactivity, and high yields. A variety of novel acetals can be readily accessed via this new method.

  一种有效的Pd（II）催化的双未活化C（sp 3）–H烷氧基化反应已被开发用于制备对称和不对称的缩醛。该新反应显示出良好的官能团耐受性，出色的反应性和高收率。通过这种新方法可以很容易地获得各种新型的缩醛。
• Weak, bidentate chelating group assisted cross-coupling of C(sp³)–H bonds in aliphatic acid derivatives with aryltrifluoroborates
  作者：Zhihua Cai、Shangda Li、Yuzhen Gao、Lei Fu、Gang Li

  DOI：10.1039/c8cc07481j

  日期：——

  A protocol of Pd(II)-catalyzed, weak bidentate directing group assisted β-C(sp3)–H activation/cross-coupling with organoboron reagents has been achieved, affording arylation of aliphatic acid derivatives that contain α-hydrogen atoms in moderate to good yields. The potential of this method for an asymmetric β-C(sp3)–H arylation via desymmetrization was also presented.

  已实现了由Pd（II）催化的弱双齿指导基团辅助的β-C（sp 3）-H活化/与有机硼试剂交叉偶联的方案，使含α-氢原子的脂肪族酸衍生物芳构化高产。还介绍了该方法通过去对称化进行不对称β-C（sp 3）-H芳构化的潜力。
• Carbamoyl derivatives
  申请人：Imperial Chemical Industries PLC

  公开号：US05286740A1

  公开（公告）日：1994-02-15

  The present invention concerns novel carbamoyl derivatives of formula I, set out herein, which antagonize the pharmacological actions of one or more of the arachidonic acid metabolites known as leukotrienes, making them useful whenever such antagonism is desired, such as in the treatment of those diseases in which leukotrienes are implicated, for example, in the treatment of allergic or inflammatory diseases, or of endotoxic or traumatic shock conditions. The invention also provides pharmaceutical compositions containing the novel derivatives for use in such treatments, methods for their use and processes and intermediates for the manufacture of the novel derivatives.

  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。
• OXO-HETEROCYCLIC SUBSTITUTED CARBOXYLIC ACID DERIVATIVES AND THE USE THEREOF
  申请人：Hahn Michael

  公开号：US20110034450A1

  公开（公告）日：2011-02-10

  The present application relates to novel carboxylic acid derivatives having an oxo-substituted azaheterocyclic partial structure, processes for their preparation, their use for the treatment and/or prophylaxis of diseases, and their use for producing medicaments for the treatment and/or prophylaxis of diseases, especially for the treatment and/or prevention of cardiovascular disorders.

  本申请涉及具有氧代取代的氮杂杂环部分结构的新型羧酸衍生物，其制备方法，其用于治疗和/或预防疾病的用途，以及其用于生产用于治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防心血管疾病的用途。
• Process for preparing (2R)-methyl-4,4,4-trifluorobutylamine
  申请人：Imperial Chemical Industries PLC

  公开号：US05274118A1

  公开（公告）日：1993-12-28

  A process for the preparation of (2R)-methyl-4,4,4-trifluorobutylamine, or an acid addition salt thereof which comprises a) acylating an optically active amine with 2-methyl-4,4,4-trifluorobutanoic acid or a reactive derivative thereof to afford a butyramide; b) separating (R)-diastereomeric butyramide from (S)-diastereomeric butyramide; and c) converting the (R)-diastereomeric butyramide into the desired (2R)-methyl-4,4,4-trifluorobutylamine, or an acid addition salt thereof. The product may be acylated with a carboxylic acid of formula III ##STR1## wherein U is carboxy, or a reactive derivative thereof to afford (R)-4-[5-(N-[4,4,4-trifluoro-2-methylbutyl]carbamoyl)-1-methylindol-3-yl-m ethyl]-3-methoxy-N-o-tolylsulphonylbenzamide. The indole is useful as a leukotriene antagonist, for example in the treatment of asthma or allergic rhinitis.

  制备（2R）-甲基-4,4,4-三氟丁基胺或其酸加成盐的过程包括：a)用2-甲基-4,4,4-三氟丁酸或其反应衍生物酰化手性胺以得到丁酰胺；b)将（R）-对映异构体丁酰胺与（S）-对映异构体丁酰胺分离；c)将（R）-对映异构体丁酰胺转化为所需的（2R）-甲基-4,4,4-三氟丁基胺或其酸加成盐。该产品可与公式III的羧酸进行酰化反应，其中U是羧基或其反应衍生物，以得到（R）-4-[5-(N-[4,4,4-三氟-2-甲基丁基]氨基甲酰)-1-甲基吲哚-3-基甲基]-3-甲氧基-N-邻甲苯磺酰苯甲酰胺。该吲哚化合物可用作白三烯拮抗剂，例如用于治疗哮喘或过敏性鼻炎。