dimethyl N-ethoxycarbonylpiperidine-4-phosphonate | 278596-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: dimethyl N-ethoxycarbonylpiperidine-4-phosphonate
• 英文别名: Ethyl 4-dimethoxyphosphorylpiperidine-1-carboxylate
• CAS: 278596-05-7
• 化学式: C₁₀H₂₀NO₅P
• 分子量: 265.246
• InChiKey: CSJVQTLAXPMPEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dimethyl N-ethoxycarbonylpiperidine-2-phosphonate 生成 dimethyl N-ethoxycarbonylpiperidine-4-phosphonate
  参考文献：
  名称：

  Process for preparing tricyclic compounds having antihistaminic activity

  摘要：

  揭示了一种制备具有以下结构的化合物的过程：其中R1从以下组中选择：烷基，烯基，炔基，芳基，芳基烷基，环烷基和环烷基烷基，R1可以选择地被来自卤素、—OH、烷基、烷氧基或—CF3的取代基取代，所述过程包括以下步骤：(a)将具有以下结构的酮与具有以下结构的碳负离子反应，其中R1如上定义，R2和R3独立地选自—ORA和—RA组成的组，其中RA是烷基、苯基、取代苯基、环烷基、取代环烷基、环烷基烷基或取代环烷基烷基；(b)用质子化剂处理步骤(a)中的反应混合物；和(c)热分解产物16，形成式(I)的化合物。通过这种方法制备的化合物具有抗组胺活性，例如洛拉替丁。还揭示了具有以下结构的新型中间体，其中R1、R2和R3如上定义。

  公开号：

  US06271378B1

文献信息

• PROCESS FOR PREPARING TRICYCLIC COMPOUNDS HAVING ANTIHISTAMINIC ACTIVITY
  申请人：SCHERING CORPORATION

  公开号：EP1140899B1

  公开（公告）日：2003-09-10
• US6271378B1
  申请人：——

  公开号：US6271378B1

  公开（公告）日：2001-08-07
• [EN] PROCESS FOR PREPARING TRICYCLIC COMPOUNDS HAVING ANTIHISTAMINIC ACTIVITY<br/>[FR] PROCEDE DE PREPARATION DE COMPOSES TRICYCLIQUES AYANT UNE ACTIVITE ANTIHISTAMINIQUE
  申请人：SCHERING CORP

  公开号：WO2000037457A1

  公开（公告）日：2000-06-29

  Disclosed is a process for preparing a compound having formula (I) wherein R1 is selected from the group consisting of: alkyl, alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, and cycloalkyalkyl, R1 being optionally substituted by substituents selected from halo, -OH, alkyl, alkoxy, or -CF¿3?, said process comprising the following steps: (a) reacting a ketone having formula (A) with a carbanion having formula (B) wherein R?1¿ is defined above, and R?2 and R3¿ are independently selected from the group consisting of -OR?A and -RA¿; wherein RA is alkyl, phenyl, substituted phenyl, cycloalkyl, substituted cycloalkyl, cycloalkylalkyl, or substituted cycloalkylalkyl; (b) treating the reaction mixture from step (a) with a protonating agent to form a β-hydroxy intermediate having formula (C) wherein R?1, R2 and R3¿ are as defined above; and (c) thermally decomposing the β-hydroxy intermediate to form the compound of formula (I). The compounds made by this process have antihistaminic activity, e.g., loratadine. Also disclosed is a process for preparing descarboethoxyloratadine, by carrying out the process above, and converting the product to descarboethoxyloratadine. Also disclosed are novel intermediates having formula (II) and (III) wherein R?1, R2 and R3¿ are as defined above.