Acetic acid tert-butylcarbamoyl-cyano-methyl-methyl ester | 799778-93-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid tert-butylcarbamoyl-cyano-methyl-methyl ester
• 英文别名: [1-(Tert-butylamino)-2-cyano-1-oxopropan-2-yl] acetate
• CAS: 799778-93-1
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: VCMOKTOTFVSOJF-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C(Solv: ethanol (64-17-5))
• 沸点：
  369.6±32.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetic acid tert-butylcarbamoyl-cyano-methyl-methyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 23.0h， 以73%的产率得到3-Acetylamino-N-tert-butyl-2-hydroxy-2-methyl-propionamide
  参考文献：
  名称：

  Three-Component Condensation Leading to β-Amino Acid Diamides:  Convergent Assembly of β-Peptide Analogues

  摘要：

  A Passerini condensation of acyl cyanides, carboxylic acids, and isonitriles has been developed that affords efficient access to functionalized diamides as well as beta-peptides of alpha-hydroxy-beta-amino acids. Such compounds are protease-resistant and form stable helical and sheet structures when incorporated into larger peptides. N-Protected alpha-amino acids and isocyanoesters derived from alpha-amino acids participate in the condensation, leading to alpha/beta peptides embodying the heterogeneous alpha/beta/alpha backbone motif, recent examples of which display antibiotic activity.

  DOI：

  10.1021/ja0450152
• 作为产物：
  描述：

  丙酮腈 、 异氰酸叔丁酯 、 溶剂黄146 反应 1.17h， 以67%的产率得到Acetic acid tert-butylcarbamoyl-cyano-methyl-methyl ester
  参考文献：
  名称：

  Three-Component Condensation Leading to β-Amino Acid Diamides:  Convergent Assembly of β-Peptide Analogues

  摘要：

  A Passerini condensation of acyl cyanides, carboxylic acids, and isonitriles has been developed that affords efficient access to functionalized diamides as well as beta-peptides of alpha-hydroxy-beta-amino acids. Such compounds are protease-resistant and form stable helical and sheet structures when incorporated into larger peptides. N-Protected alpha-amino acids and isocyanoesters derived from alpha-amino acids participate in the condensation, leading to alpha/beta peptides embodying the heterogeneous alpha/beta/alpha backbone motif, recent examples of which display antibiotic activity.

  DOI：

  10.1021/ja0450152

文献信息

• Tandem multicomponent/click reactions: synthesis of functionalized oxazoles and tetrazoles from acyl cyanides
  作者：Isabelle F. Clémençon、Bruce Ganem

  DOI：10.1016/j.tet.2007.03.127

  日期：2007.8

  The combination of multicomponent condensations with post-condensation dipolar cycloaddition reactions provides a useful route to densely functionalized oxazoles and tetrazoles in just two synthetic steps. (c) 2007 Elsevier Ltd. All rights reserved.