2-<(tert-butyloxycarbonyl)amino>-N-(3-hydroxybenzyl)acetamide | 147949-76-6

• 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-<(tert-butyloxycarbonyl)amino>-N-(3-hydroxybenzyl)acetamide
• 英文别名: tert-butyl N-[2-[(3-hydroxyphenyl)methylamino]-2-oxoethyl]carbamate
• CAS: 147949-76-6
• 化学式: C₁₄H₂₀N₂O₄
• mdl: MFCD24391894
• 分子量: 280.324
• InChiKey: GLFLPDHXHRCGGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<(tert-butyloxycarbonyl)amino>-N-(3-hydroxybenzyl)acetamide 在 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 18-Nitro-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-10,13-dione
  参考文献：
  名称：

  14元大环的新途径：替考拉宁模型FOG环的合成

  摘要：

  为合成14元大环化合物，开发了一种基于分子内S N Ar反应的新策略。容易进行大环化的原因已经得到了先进的研究，并得到了计算研究的支持。

  DOI：

  10.1016/0040-4039(95)00015-5
• 作为产物：
  描述：

  3-氰基苯酚 在 盐酸 、 甲醇 、 硼烷四氢呋喃络合物 、 氯甲酸乙酯 、 三乙胺 作用下， 生成 2-<(tert-butyloxycarbonyl)amino>-N-(3-hydroxybenzyl)acetamide
  参考文献：
  名称：

  14元大环的新途径：替考拉宁模型FOG环的合成

  摘要：

  为合成14元大环化合物，开发了一种基于分子内S N Ar反应的新策略。容易进行大环化的原因已经得到了先进的研究，并得到了计算研究的支持。

  DOI：

  10.1016/0040-4039(95)00015-5

文献信息

• A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction
  作者：Jieping Zhu、Rene Beugelmans、Sebastien Bourdet、Jacqueline Chastanet、George Roussi

  DOI：10.1021/jo00125a026

  日期：1995.10

  An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.
• SNAr-Based Macrocyclization: An Application to the Synthesis of Vancomycin Family Models
  作者：Rene Beugelmans、Girij Pal Singh、Michele Bois-Choussy、Jacqueline Chastanet、Jieping Zhu

  DOI：10.1021/jo00098a010

  日期：1994.9

  The first examples of macrocyclization using the intramolecular SNAr reaction are reported. The method has allowed the efficient preparation of the elusive 16-membered macrocyclic COD and DOE rings related to vancomycin. The mild conditions used allow the incorporation of very racemization-prone amino acids, such as p-methoxyphenylglycine, into the peptide chain. After serving as an activator, the nitro group ortho to the diaryl ether linkage is converted either into a chlorine or a hydrogen atom, thus achieving the substitution pattern found in the vancomycin family of glycopeptides. When compound 20 was submitted to the same macrocyclization conditions, two atropisomers 21 and 22 were isolated and characterized.
• Vancomycin and ristocetin models: synthesis via the Ullmann macrocyclization reaction
  作者：Dale L. Boger、Yuji Nomoto、Bradley R. Teegarden

  DOI：10.1021/jo00058a024

  日期：1993.3

  The preparations of 2 and 3, the parent skeletons of the CD and DE diphenyl ether 16-membered ring systems of vancomycin and ristocetin, based on the implementation of an intramolecular Ullmann macrocyclization reaction are detailed. Additional studies which define the scope of substrates suitable for use in the Ullmann macrocyclization reaction are described including a limited study of those bearing centers capable of racemization. Within the limited series of agents examined, Ullmann macrocyclization closure of the DE ring system was found to occur at a faster rate and in higher overall yields than those providing the CD ring system. N-Methylation of the amide linking chain decelerates or inhibits Ullmann macrocyclization and a-substitution of the central amino acid of the linking chain significantly increases the cyclization conversions. Racemization of the central amino acid of the linking amide chain was found to be minimal (5%) under reaction conditions where the secondary amides are deliberately deprotonated prior to exposure of the substrate to the thermal, basic reaction conditions.
• A new access to 14-membered macrocycle: Synthesis of model F-O-G ring of teicoplanin
  作者：René Beugelmans、Sebastien Bourdet、Jieping Zhu

  DOI：10.1016/0040-4039(95)00015-5

  日期：1995.2

  A new strategy based upon the intramolecular SNAr reaction was developped for the synthesis of 14-membered macrocycle. The reason for the easy macrocyclisation was advanced and supported by computational studies.

  为合成14元大环化合物，开发了一种基于分子内S N Ar反应的新策略。容易进行大环化的原因已经得到了先进的研究，并得到了计算研究的支持。