2-(3,5-dimethoxyphenyl)propan-2-yl 2-(5,7-dinitroindolin-1-yl)-2-oxoethylcarbamate | 1161881-30-6

• 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: 2-(3,5-dimethoxyphenyl)propan-2-yl 2-(5,7-dinitroindolin-1-yl)-2-oxoethylcarbamate
• 英文别名: 2-(3,5-dimethoxyphenyl)propan-2-yl N-[2-(5,7-dinitro-2,3-dihydroindol-1-yl)-2-oxoethyl]carbamate
• CAS: 1161881-30-6
• 化学式: C₂₂H₂₄N₄O₉
• 分子量: 488.454
• InChiKey: DMPGOKJLOILPCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  169
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethoxyphenyl)propan-2-yl 2-(5,7-dinitroindolin-1-yl)-2-oxoethylcarbamate 、 甘氨酸叔丁酯盐酸盐 在 三乙胺 作用下， 以 乙腈 为溶剂， 以93%的产率得到tert-butyl (((2-(3,5-dimethoxyphenyl)propan-2-yl)oxy)carbonyl)glycylglycinate
  参考文献：
  名称：

  Towards a Photochemical Synthesis of Peptides

  摘要：

  肽的实验室制备，曾经是一个挑战，现在已经成为可以自动化的标准操作。然而，在特定情况下（例如在细胞或微流体装置中），需要相对严苛条件（强酸或碱）去除特定保护基和反应偶联剂可能会有问题。在这篇文章中，我们描述了我们努力实现完全光化学方法合成肽的努力，其中偶联和去保护步骤均使用光而不是试剂。为了在一次只促进两个步骤中的一个，使用单色光。

  DOI：

  10.2533/chimia.2013.896
• 作为产物：
  描述：

  2-(3,5-dimethoxyphenyl)propan-2-yl (2-bromo-3,5-dinitrophenethylcarbamoyl)methylcarbamate 在 potassium carbonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-二环己基磷-2'-甲基联苯 作用下， 以 甲苯 、 乙腈 为溶剂， 以76%的产率得到2-(3,5-dimethoxyphenyl)propan-2-yl 2-(5,7-dinitroindolin-1-yl)-2-oxoethylcarbamate
  参考文献：
  名称：

  Preparation of Photoactivable Amino Acid Derivatives

  摘要：

  A range of N-protected-alpha-amino acyl-5,7-dinitroindolines 3a-z were prepared in good yields from commercially available N-protected-alpha-amino acids 1a-z by a two-step sequence of acylation and intramolecular amide N-arylation. Subsequent photochemical acylation of the N-protected-alpha-amino acyl-5,7-dinitroindolines 3e,g,r afforded the corresponding N-protected-alpha-amino acid amides 22e,g,r (77-92%) under mild conditions. All these reactions occurred with complete retention of chirality as evidenced by NMR analysis. This scheme provides an attractive and alternative method to the conventional acylation of alpha-amino acids, especially in cases where the amide bond needs to be formed without the use of a coupling reagent.

  DOI：

  10.1021/jo900442p

文献信息

• Preparation of Photoactivable Amino Acid Derivatives
  作者：Jean-Luc Débieux、Christian G. Bochet

  DOI：10.1021/jo900442p

  日期：2009.6.19

  A range of N-protected-alpha-amino acyl-5,7-dinitroindolines 3a-z were prepared in good yields from commercially available N-protected-alpha-amino acids 1a-z by a two-step sequence of acylation and intramolecular amide N-arylation. Subsequent photochemical acylation of the N-protected-alpha-amino acyl-5,7-dinitroindolines 3e,g,r afforded the corresponding N-protected-alpha-amino acid amides 22e,g,r (77-92%) under mild conditions. All these reactions occurred with complete retention of chirality as evidenced by NMR analysis. This scheme provides an attractive and alternative method to the conventional acylation of alpha-amino acids, especially in cases where the amide bond needs to be formed without the use of a coupling reagent.
• Towards a Photochemical Synthesis of Peptides
  作者：Christian G. Bochet

  DOI：10.2533/chimia.2013.896

  日期：——

  The laboratory preparation of peptides, once a challenge, is now a standard operation that can be automatised. However, the need for particular protecting groups requiring relatively harsh conditions for their removal (strong acids or bases) and reactive coupling agents can be problematic in specific cases (e.g. in a cell or in a microfluidic device). In this account, we describe our efforts towards a fully photochemical approach to peptide synthesis, where both the coupling and the deprotection steps use light instead of reagents. In order to selectively promote one of the two steps at a time, monochromatic light is used.

  肽的实验室制备，曾经是一个挑战，现在已经成为可以自动化的标准操作。然而，在特定情况下（例如在细胞或微流体装置中），需要相对严苛条件（强酸或碱）去除特定保护基和反应偶联剂可能会有问题。在这篇文章中，我们描述了我们努力实现完全光化学方法合成肽的努力，其中偶联和去保护步骤均使用光而不是试剂。为了在一次只促进两个步骤中的一个，使用单色光。