N-cycloheptylnicotinamide | 346720-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-cycloheptylnicotinamide
• 英文别名: N-cycloheptylpyridine-3-carboxamide
• CAS: 346720-18-1
• 化学式: C₁₃H₁₈N₂O
• mdl: MFCD00784189
• 分子量: 218.299
• InChiKey: YCNAIZSBSFXJGD-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86 °C
• 沸点：
  427.6±18.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  硫代烟酸 、 环庚胺 在 N,O-双三甲硅基乙酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到N-cycloheptylnicotinamide
  参考文献：
  名称：

  In Situ Carboxyl Activation Using a Silatropic Switch: A New Approach to Amide and Peptide Constructions

  摘要：

  The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1 degrees and 2 degrees amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.

  DOI：

  10.1021/ja2065158

文献信息

• Processes For Forming Amide Bonds And Compositions Related Thereto
  申请人：Liebeskind Lanny S.

  公开号：US20120107902A1

  公开（公告）日：2012-05-03

  The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.

  本披露涉及生产酰胺键的方法及相关试剂。在某些实施例中，本披露涉及生产酰胺的方法，包括混合O-硅基硫代酯和胺，以形成酰胺。在另一实施例中，本披露涉及混合硫酸、硅基化试剂和胺的方法，以形成酰胺。
• PROCESSES FOR FORMING AMIDE BONDS AND COMPOSITIONS RELATED THERETO
  申请人：EMORY UNIVERSITY

  公开号：US20150315129A1

  公开（公告）日：2015-11-05

  The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.

  本公开涉及制备酰胺键及其相关试剂的方法。在一些实施例中，本公开涉及制备酰胺的方法，包括混合O-硅基硫酰酯和胺，在形成酰胺的条件下进行。在另一实施例中，本公开涉及混合硫酸酯、硅基化试剂和胺，在形成酰胺的条件下进行。
• US8921599B2
  申请人：——

  公开号：US8921599B2

  公开（公告）日：2014-12-30
• US9382193B2
  申请人：——

  公开号：US9382193B2

  公开（公告）日：2016-07-05
• In Situ Carboxyl Activation Using a Silatropic Switch: A New Approach to Amide and Peptide Constructions
  作者：Wenting Wu、Zhihui Zhang、Lanny S. Liebeskind

  DOI：10.1021/ja2065158

  日期：2011.9.14

  The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1 degrees and 2 degrees amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.