2-(1-acetylamino-ethyl)-thiazole-4-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-amide | 959853-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(1-acetylamino-ethyl)-thiazole-4-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-amide
• 英文别名: (R)-N-(2-(1H-indol-3-yl)ethyl)-2-(1-acetamidoethyl)thiazole-4-carboxamide；bacillamide C；(-)-bacillamide C；(R)-bacillamide C；2-[(1R)-1-acetamidoethyl]-N-[2-(1H-indol-3-yl)ethyl]-1,3-thiazole-4-carboxamide
• CAS: 959853-22-6
• 化学式: C₁₈H₂₀N₄O₂S
• 分子量: 356.448
• InChiKey: NNOWKGATWUOFNF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-ethyl 2-(1-acetamidoethyl)thiazole-4-carboxylate 在 盐酸 、 4-二甲氨基吡啶 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 7.0h， 生成 2-(1-acetylamino-ethyl)-thiazole-4-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-amide
  参考文献：
  名称：

  Total syntheses of bacillamide C and neobacillamide A; revision of their absolute configurations

  摘要：

  The enantiospecific syntheses of both enantiomers of bacillamide C and neobacillamide A are described, along with the measurement of their optical activities, leading to the revision of the proposed absolute configurations of these natural products. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.11.001

文献信息

• (−)-Bacillamide C: the convergent approach
  作者：Wei Wang、Shannon Joyner、Kareem Andrew Sameer Khoury、Alexander Dömling

  DOI：10.1039/b918214d

  日期：——

  The newly discovered natural product bacillamide C and several derivatives were convergently synthesized for the first time and in only three steps. The key transformation constitutes a thiazole Ugi multicomponent reaction. These compounds will serve to elucidate chemical biology and SAR of this potent anti-algae natural product and shows the synthetic pathway to related natural products.

  新发现的天然产物巴卡拉酰胺 C 及其几种衍生物首次在三个步骤内被聚合合成。关键的转化过程是噻唑乌基多组分反应。这些化合物将有助于阐明这种强效抗藻天然产物的化学生物学和 SAR，并展示了相关天然产物的合成途径。
• Total syntheses of bacillamide C and neobacillamide A; revision of their absolute configurations
  作者：Verónica Martínez、Danilo Davyt

  DOI：10.1016/j.tetasy.2013.11.001

  日期：2013.12

  The enantiospecific syntheses of both enantiomers of bacillamide C and neobacillamide A are described, along with the measurement of their optical activities, leading to the revision of the proposed absolute configurations of these natural products. (C) 2013 Elsevier Ltd. All rights reserved.