2-(4-(4-bromobutanoyl)phenyl)-2-methylpropanenitrile | 394222-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-(4-bromobutanoyl)phenyl)-2-methylpropanenitrile
• 英文别名: 4-(4-Bromo-1-Oxobutyl)-α,α-Dimethylphenylacetonitrile；2-[4-(4-Bromobutanoyl)phenyl]-2-methylpropanenitrile
• CAS: 394222-38-9
• 化学式: C₁₄H₁₆BrNO
• 分子量: 294.191
• InChiKey: DUTNEPMIXGKXNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-(4-bromobutanoyl)phenyl)-2-methylpropanenitrile 在 sodium tetrahydroborate 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 21.0h， 生成 非索芬那定
  参考文献：
  名称：

  Novel Preparation of H₁ Receptor Antagonist Fexofenadine

  摘要：

  A novel synthetic route for the preparation of H-1 receptor antagonist fexofenadine is described. The synthetic route started from the para-substituted aromatic derivative of methyl 4-(cyanomethyl)benzoate, 2, and gave fexofenadine in 26.0% overall yield via six steps. The whole process featured a method wherein fexofenadine could be obtained in excellent quality without ortho- or meta-unpurified regioisomers.

  DOI：

  10.1021/op100090j
• 作为产物：
  描述：

  2-(4-(4-hydroxybutanoyl)phenyl)-2-methylpropanenitrile 在 氢溴酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以160 g的产率得到2-(4-(4-bromobutanoyl)phenyl)-2-methylpropanenitrile
  参考文献：
  名称：

  Novel Preparation of H₁ Receptor Antagonist Fexofenadine

  摘要：

  A novel synthetic route for the preparation of H-1 receptor antagonist fexofenadine is described. The synthetic route started from the para-substituted aromatic derivative of methyl 4-(cyanomethyl)benzoate, 2, and gave fexofenadine in 26.0% overall yield via six steps. The whole process featured a method wherein fexofenadine could be obtained in excellent quality without ortho- or meta-unpurified regioisomers.

  DOI：

  10.1021/op100090j

文献信息

• Visible-Light Mediated Oxidative Fragmentation of Ethers and Acetals by Means of Fe(III) Catalysis
  作者：Rickard Lindroth、Alica Ondrejková、Carl-Johan Wallentin

  DOI：10.1021/acs.orglett.2c00231

  日期：2022.3.4

  A new method employing iron(III) acetylacetonate along with visible light is described to effect oxidative ring opening of cyclic ethers and acetals with unparalleled efficiency. The method allows for a photocatalytic radical chemistry approach to functionalize relatively inert cyclic ethers into useful synthetic intermediates. The methodology sheds further light on the use of underexplored iron complexes

  描述了一种使用乙酰丙酮铁 (III) 和可见光的新方法，以无与伦比的效率实现环状醚和缩醛的氧化开环。该方法允许使用光催化自由基化学方法将相对惰性的环醚官能化成有用的合成中间体。该方法进一步阐明了在可见光光化学环境中使用未充分探索的铁配合物，并说明简单的 Fe(III) 配合物可以从4 个LMCT 激发态引发氧化还原过程。
• Processes for the production of fexofenadine
  申请人：——

  公开号：US20030166682A1

  公开（公告）日：2003-09-04

  An improved process for the manufacture of fexofenadine is described in which a compound of formula (F): wherein R 2 represents COOH, COO—C 1-6 alkyl or CN; and R 3 represents hydrogen, mesylate, triflate, tosylate or carboxy-C 1-6 -alkyl, or a salt thereof is prepared by: (I) reacting a compound of formula (B): wherein R1 represents hydrogen or carboxy-C 1-6 -alkyl; and R 2 is a hereinbefore defined, with a copper and/or silver compound in the presence of palladium or a compound thereof to yield a compound of formula (C): wherein R 1 , and R 2 are as hereinbefore defined; (II) converting said compound of formula (C) into a compound of formula (E): wherein R 2 and R 3 are as hereinbefore defined and R 4 represents a halogen atom, and (III) reacting said compound of formula (E) with azacyclonol.

  本发明描述了一种改进的费索芬丁制造工艺，其中通过以下步骤制备式（F）的化合物：其中R2代表COOH，COO-C1-6烷基或CN；R3代表氢、甲磺酸盐、三氟甲磺酸盐、对甲苯磺酸盐或羧基-C1-6-烷基，或其盐：（I）将式（B）的化合物与铜和/或银化合物在钯或其化合物的存在下反应，以产生式（C）的化合物：其中R1和R2如上所述；（II）将式（C）的化合物转化为式（E）的化合物：其中R2和R3如上所述，R4代表卤素原子；（III）将式（E）的化合物与氮杂环己烷反应。
• [EN] NEW PROCESSES FOR THE PRODUCTION OF FEXOFENADINE<br/>[FR] NOUVEAUX PROCESSUS DE PRODUCTION DE FEXOFENADINE
  申请人：TEXCONTOR ETS

  公开号：WO2002010115A1

  公开（公告）日：2002-02-07

  An improved process for the manufacture of fexofenadine is described in which a compound of formula (F): wherein R2 represents COOH, COO-C1-6 alkyl or CN; and R3 represents hydrogen, mesylate, triflate, tosylate or carboxy-C1-6-alkyl, or a salt thereof is prepared by: (I) reacting a compound of formula (B): wherein R1 represents hydrogen or carboxy-C1-6-alkyl; and R2 is a hereinbefore defined, with a copper and/or silver compound in the presence of palladium or a compound thereof to yield a compound of formula (C): wherein R1, and R2 are as hereinbefore defined; (II) converting said compound of formula (C) into a compound of formula (E): wherein R2 and R3 are as hereinbefore defined and R4 represents a halogen atom, and (III) reacting said compound of formula (E) with azacyclonol.

  本文描述了一种改进的费索非那定制造工艺，其中通过以下步骤制备化合物（F）的盐：其中R2代表COOH、COO-C1-6烷基或CN；R3代表氢、甲磺酸盐、三氟甲磺酸盐、对甲苯磺酸盐或羧基-C1-6-烷基，或其盐：(I)反应式(B)的化合物：其中R1代表氢或羧基-C1-6-烷基；R2如上所述，与钯或其化合物在铜和/或银化合物的存在下反应，得到式(C)的化合物：其中R1和R2如上所述；(II)将式(C)的化合物转化为式(E)的化合物：其中R2和R3如上所述，R4代表卤素原子；(III)将式(E)的化合物与氮杂环己醇反应。
• PROCESSES FOR THE PRODUCTION OF FEXOFENADINE
  申请人：Texcontor Etablissement

  公开号：EP1307423B1

  公开（公告）日：2008-03-19
• NEW PROCESSES FOR THE PRODUCTION OF FEXOFENADINE
  申请人：Texcontor Etablissement

  公开号：EP1307423A1

  公开（公告）日：2003-05-07