2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile | 169280-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile
• 英文别名: 2-(4-cyclopropanecarbonyl-phenyl)-2-methyl-propionitrile；2-(4-(Cyclopropanecarbonyl)phenyl)-2-methylpropanenitrile；2-[4-(cyclopropanecarbonyl)phenyl]-2-methylpropanenitrile
• CAS: 169280-06-2
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: OEGDIOHJCJQYBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• 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-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 2-[4-(cyclopropanecarbonyl)phenyl]-2-methylpropanamide
  参考文献：
  名称：

  Intermediates useful for the preparation of antihistaminic piperidine derivatives

  摘要：

  本发明涉及一种新型中间体和过程，该中间体和过程在制备某些抗组胺酸哌啶衍生物的过程中非常有用，其化学式为 其中 W代表—C(═O)—或—CH(OH)—; R1代表氢或羟基; R2代表氢; R1和R2一起形成连接R1和R2的碳原子之间的第二键; n为1至5的整数; m为0或1的整数; R3为—COOH或—COO烷基，其中烷基基团具有1至6个碳原子，直链或支链，A的每个是氢或羟基;以及其药用可接受盐和各自的光学异构体， 但是当R1和R2一起形成连接R1和R2的碳原子之间的第二键或当R1代表羟基时，m为0。

  公开号：

  US06348597B2
• 作为产物：
  描述：

  2-(4-(4-hydroxybutanoyl)phenyl)-2-methylpropanenitrile 在 氢溴酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile
  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
• 作为试剂：
  描述：

  α,α-二苯基-4-哌啶甲醇 在 2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile 、 对甲苯磺酸 作用下， 以 邻二甲苯 为溶剂， 以49%的产率得到4-二苯基亚甲基哌啶
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF FEXOFENADINE AND OF INTERMEDIATES USED THEREIN
  [FR] PROCÉDÉ DE PRÉPARATION DE FEXOFÉNADINE ET D'INTERMÉDIAIRES UTILISÉS DANS CELLE-CI

  摘要：

  提供一种新的制备费洛芬那定及其相关中间体的方法，可用于费洛芬那定的制备。

  公开号：

  WO2017068129A1

文献信息

• [EN] Process for the production of 2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile<br/>[FR] PROCÉDÉ POUR LA PRODUCTION DE 2-[4-(CYCLOPROPANECARBONYL)PHÉNYL]-2-MÉTHYL-PROPANENITRILE
  申请人：SANOFI AVENTIS DEUTSCHLAND

  公开号：WO2016116555A1

  公开（公告）日：2016-07-28

  A new process for the production of 2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl- propanenitrile is described. This compound can be used for the production of drugs, such as Fexofenadine.

  描述了一种生产2-[4-(环丙基甲酰基)苯基]-2-甲基丙腈的新工艺。这种化合物可用于生产药物，如非索非丁。
• Intermediates useful for the preparation of antihistaminic piperidine
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US06147216A1

  公开（公告）日：2000-11-14

  The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula ##STR1## wherein W represents --C(.dbd.O)-- or --CH(OH)--; R.sub.1 represents hydrogen or hydroxy; R.sub.2 represents hydrogen; R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; n is an integer of from 1 to 5; m is an integer 0 or 1; R.sub.3 is --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched each of A is hydrogen or hydroxy; and pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R.sub.1 and R.sub.2 are ta to form a second bond between the carbon R.sub.1 and R.sub.2 or where R.sub.1 represented hydroxy integer 0.

  本发明涉及一种新型中间体和工艺，可用于制备某些抗组胺酸哌啶衍生物，其化学式为##STR1##其中W代表--C(.dbd.O)--或--CH(OH)--；R.sub.1代表氢或羟基；R.sub.2代表氢；R.sub.1和R.sub.2共同形成连接R.sub.1和R.sub.2的碳原子之间的第二键；n为1至5的整数；m为0或1的整数；R.sub.3为--COOH或--COOalkyl，其中alkyl基含有1至6个碳原子，是直链或支链；每个A都是氢或羟基；以及其药用盐和单体光学异构体，但其中R.sub.1和R.sub.2形成连接R.sub.1和R.sub.2的碳原子之间的第二键或R.sub.1代表羟基时除外。
• 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。
• PROCESS FOR THE PRODUCTION OF 2-[4-(CYCLOPROPANECARBONYL)PHENYL]-2-METHYL-PROPANENITRILE
  申请人：SANOFI-AVENTIS DEUTSCHLAND GMBH

  公开号：US20170369440A1

  公开（公告）日：2017-12-28

  A new process for the production of 2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile is described. This compound can be used for the production of drugs, such as Fexofenadine.

  一种生产2-[4-(环丙烷羰基)苯基]-2-甲基丙腈的新工艺被描述。该化合物可用于制造药物，如费索非那定。
• Intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives
  申请人：Aventisub II Inc.

  公开号：EP2261208A1

  公开（公告）日：2010-12-15

  The present invention is related to novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of formula (I) wherein W represents -C(=O)- or -CH(OH)-; R1 represents hydrogen or hydroxy; R2 represents hydrogen; R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2; n is an integer of from 1 to 5; m is an integer 0 or 1; R3 is -COOH or -COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; each of A is hydrogen or hydroxy; and pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R1 and R2 are taken together to form a second bond between the carbon atoms bearing R1 and R2 or where R1 represented hydroxy, m is an integer 0.

  本发明涉及一种新型中间体和制备某些抗组胺哌啶衍生物的方法，其化学式为(I)，其中W代表-C（=O）-或-CH（OH）-；R1代表氢或羟基；R2代表氢；R1和R2一起形成连接带有R1和R2的碳原子之间的第二个键；n为1至5的整数；m为0或1的整数；R3为-COOH或-COOalkyl，其中烷基具有1至6个碳原子，是直链或支链；每个A是氢或羟基；以及其药学上可接受的盐和单一光学异构体，但当R1和R2一起形成连接带有R1和R2的碳原子之间的第二个键或当R1代表羟基时，m为0。