ethyl (S)-1-(2-thiopheneacetyl)-3-piperidinecarboxylate | 310454-69-4

• 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: ethyl (S)-1-(2-thiopheneacetyl)-3-piperidinecarboxylate
• 英文别名: (S)-ethyl 1-(2-thiopheneacetyl)-3-piperidinecarboxylate；ethyl (3S)-1-(2-thiophen-2-ylacetyl)piperidine-3-carboxylate
• CAS: 310454-69-4
• 化学式: C₁₄H₁₉NO₃S
• mdl: MFCD25104134
• 分子量: 281.376
• InChiKey: NWYHIRYENVSJSF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (S)-1-(2-thiopheneacetyl)-3-piperidinecarboxylate 生成 (S)-1-(2-thiopheneacetyl)-3-piperidinecarboxylic acid
  参考文献：
  名称：

  Immunopotentiator agents

  摘要：

  新化合物和制备方法，免疫增强组合物，以及增强宿主动物免疫系统的方法。该方法包括向动物施用公式I或公式II的免疫增强化合物或生理上可接受的盐的有效量。

  公开号：

  US06664271B1
• 作为产物：
  描述：

  3-哌啶甲酸乙酯 在 sodium carbonate 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 15.5h， 生成 ethyl (S)-1-(2-thiopheneacetyl)-3-piperidinecarboxylate
  参考文献：
  名称：

  Development of an Efficient Synthesis for a Nipecotate-Containing Immunopotentiator

  摘要：

  The preparation of Elanco Animal Health immunopotentiator (S)-ethyl-1-(2-thiopheneacetyl)-3-piperidinecarboxylate (1) is described. The synthesis includes a new resolution of racemic ethyl nipecotate with dibenzoyl-L-tartaric acid. The resolved salt is found to couple directly with commercially available 2-thiopheneacetyl chloride under environmentally friendly Schotten-Baumann conditions to afford the amide in high yield. The final product is an oil which is purified by wiped film evaporative distillation.

  DOI：

  10.1021/op049941c

文献信息

• Immunopotentiator agents
  申请人：Eli Lilly and Company

  公开号：US06664271B1

  公开（公告）日：2003-12-16

  Novel compounds and methods for preparing same, immunopotentiating compositions, and a method for potentiating the immune system of a host animal. The method comprises administering to the animal an effective amount of an immunopotentiating compound of Formula I or Formula II, or a physiologically acceptable salt.

  新化合物和制备方法，免疫增强组合物，以及增强宿主动物免疫系统的方法。该方法包括向动物施用公式I或公式II的免疫增强化合物或生理上可接受的盐的有效量。
• Development of an Efficient Synthesis for a Nipecotate-Containing Immunopotentiator
  作者：Eric D. Moher、Allie E. Tripp、Lawrence C. Creemer、Jeffrey T. Vicenzi

  DOI：10.1021/op049941c

  日期：2004.7.1

  The preparation of Elanco Animal Health immunopotentiator (S)-ethyl-1-(2-thiopheneacetyl)-3-piperidinecarboxylate (1) is described. The synthesis includes a new resolution of racemic ethyl nipecotate with dibenzoyl-L-tartaric acid. The resolved salt is found to couple directly with commercially available 2-thiopheneacetyl chloride under environmentally friendly Schotten-Baumann conditions to afford the amide in high yield. The final product is an oil which is purified by wiped film evaporative distillation.