2-(4-(4-hydroxybutanoyl)phenyl)-2-methylpropanenitrile | 394222-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-(4-hydroxybutanoyl)phenyl)-2-methylpropanenitrile
• 英文别名: 4-(4-Hydroxy-1-Oxobutyl)-α,α-Dimethylphenylacetonitrile；2-[4-(4-Hydroxybutanoyl)phenyl]-2-methylpropanenitrile
• CAS: 394222-37-8
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: FLCMBFYUEIKENX-UHFFFAOYSA-N

物化性质

• 沸点：
  431.6±35.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-(4-hydroxybutanoyl)phenyl)-2-methylpropanenitrile 在 sodium tetrahydroborate 、 氢溴酸 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 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：

  sodium (4-(2-cyanopropan-2-yl)phenyl)(2-oxodihydrofuran-3(2H)-ylidene)methanolate 在 盐酸 、 水 作用下， 反应 4.0h， 以165 g的产率得到2-(4-(4-hydroxybutanoyl)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

• 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。
• PROCESSES FOR THE PRODUCTION OF FEXOFENADINE
  申请人：Texcontor Etablissement

  公开号：EP1307423B1

  公开（公告）日：2008-03-19
• US7176318B2
  申请人：——

  公开号：US7176318B2

  公开（公告）日：2007-02-13
• Novel Preparation of H₁ Receptor Antagonist Fexofenadine
  作者：Jun Huang、Wen Wang、Li-Xin Wang

  DOI：10.1021/op100090j

  日期：2010.11.19

  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.