N-{3-[N'-(2,7-Di-tert-butyl-9H-fluoren-9-ylmethoxycarbonyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamic acid ethyl ester | 295800-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-{3-[N'-(2,7-Di-tert-butyl-9H-fluoren-9-ylmethoxycarbonyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamic acid ethyl ester
• CAS: 295800-32-7
• 化学式: C₃₅H₄₁N₃O₇
• 分子量: 615.726
• InChiKey: FFRGUCMNJMVAEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  45.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  132.06
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-{3-[N'-(2,7-Di-tert-butyl-9H-fluoren-9-ylmethoxycarbonyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamic acid ethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 N-((S)-1-Butylcarbamoyl-2-methyl-propyl)-N'-{3-[N'-((S)-2-isobutyrylamino-3-phenyl-propionyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamide
  参考文献：
  名称：

  An Unnatural Amino Acid that Mimics a Tripeptide β-Strand and Forms β-Sheetlike Hydrogen-Bonded Dimers

  摘要：

  Unnatural amino acid 2 (5-HO2CCONH-2-MeO-C6H3-CONHNH2) duplicates the hydrogen-bonding functionality of one edge of a tripeptide P-strand. It is composed of hydrazine, 5-amino-2-methoxybenzoic acid, and oxalic acid groups and is designated by the three-letter abbreviation "Hao" to reflect these three components. The 2,7-di-tert-butylfluorenylmethyloxycarbonyl (Fmoc*)- and tert-butyloxycarbonyl (Boc)-protected derivatives of Hao are prepared efficiently and in high yield by the condensation of suitably protected derivatives of hydrazine, 5-amino-2-methoxybenzoic acid, and oxalic acid. Fmoc*-Hao and Boc-Hao behave like typical Fmoc- and Boc-protected amino acids and can be incorporated into peptides by standard solid-and solution-phase peptide synthesis techniques using carbodiimide coupling agents. Hao-containing peptide 9 (i-PrCO-Phe-Hao-Val-NHBu) forms a beta-sheetlike hydrogen-bonded dimer in CDCl3 acid CD3OD-CDCl3 solutions. Peptides containing Hao and natural amino acids display hydrogen-bonding surfaces that are complementary to the hydrogen-bonding edges of protein beta-sheets.

  DOI：

  10.1021/ja001142w
• 作为产物：
  描述：

  2,7-二叔丁基-9-芴甲基氯甲酸酯 在 10percent Pd/C 吡啶 、 氢气 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 5.75h， 生成 N-{3-[N'-(2,7-Di-tert-butyl-9H-fluoren-9-ylmethoxycarbonyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamic acid ethyl ester
  参考文献：
  名称：

  An Unnatural Amino Acid that Mimics a Tripeptide β-Strand and Forms β-Sheetlike Hydrogen-Bonded Dimers

  摘要：

  Unnatural amino acid 2 (5-HO2CCONH-2-MeO-C6H3-CONHNH2) duplicates the hydrogen-bonding functionality of one edge of a tripeptide P-strand. It is composed of hydrazine, 5-amino-2-methoxybenzoic acid, and oxalic acid groups and is designated by the three-letter abbreviation "Hao" to reflect these three components. The 2,7-di-tert-butylfluorenylmethyloxycarbonyl (Fmoc*)- and tert-butyloxycarbonyl (Boc)-protected derivatives of Hao are prepared efficiently and in high yield by the condensation of suitably protected derivatives of hydrazine, 5-amino-2-methoxybenzoic acid, and oxalic acid. Fmoc*-Hao and Boc-Hao behave like typical Fmoc- and Boc-protected amino acids and can be incorporated into peptides by standard solid-and solution-phase peptide synthesis techniques using carbodiimide coupling agents. Hao-containing peptide 9 (i-PrCO-Phe-Hao-Val-NHBu) forms a beta-sheetlike hydrogen-bonded dimer in CDCl3 acid CD3OD-CDCl3 solutions. Peptides containing Hao and natural amino acids display hydrogen-bonding surfaces that are complementary to the hydrogen-bonding edges of protein beta-sheets.

  DOI：

  10.1021/ja001142w