(N-tert-butyloxycarbonyl-glycylglycine)-O-pentachlorophenyl ester | 68560-42-9

• 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: (N-tert-butyloxycarbonyl-glycylglycine)-O-pentachlorophenyl ester
• 英文别名: Boc-Gly-Gly-OPCP；(2,3,4,5,6-Pentachlorophenyl) 2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetate
• CAS: 68560-42-9
• 化学式: C₁₅H₁₅Cl₅N₂O₅
• 分子量: 480.56
• InChiKey: NJIOOXOUXQIHMG-UHFFFAOYSA-N

物化性质

• 沸点：
  642.9±55.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (N-tert-butyloxycarbonyl-glycylglycine)-O-pentachlorophenyl ester 在 三氟乙酸 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  15N NMR spectroscopy. 19—spectroscopic characterization of cyclodipeptides (2,5-dioxopiperazines)

  摘要：

  AbstractVarious cyclodipeptides containing glycine, alanine, leucine, valine, phenylalanine, phenylglycine and sarcosine units were synthesized by cyclization of dipeptide pentachlorophenyl esters. The 13C and natural abundance 15N NMR spectra of these heterocycles were measured in trifluoroacetic acid and compared with the spectra of the corresponding amino acids and polypeptides. The 13C NMR carbonyl signals of all cyclodipeptides show a 1.5–4.0 ppm upfield shift relative to the corresponding polypeptides. The 15N NMR signals show no such consistent relationship. The substituent effects and the neighbouring residue effects observed in the 15N NMR spectra of the cyclodipeptides are different from those of polypeptides, while the one bond NH coupling constant of cis and trans amide groups was almost identical. The nitrogen and the carbonyl signal of the Gly units in cyclo‐Gly‐Phe show an extraordinary downfield shift, reflecting the interaction of the phenyl group with the 2,5‐dioxopiperazine ring.

  DOI：

  10.1002/mrc.1270130111

文献信息

• Jeric, Ivanka; Momcilovic, Marko; Bratos, Igor, Croatica Chemica Acta, 2006, vol. 79, # 2, p. 261 - 272
  作者：Jeric, Ivanka、Momcilovic, Marko、Bratos, Igor、Horvat, Stefica

  DOI：——

  日期：——
• US4093610A
  申请人：——

  公开号：US4093610A

  公开（公告）日：1978-06-06
• 15N NMR spectroscopy. 19—spectroscopic characterization of cyclodipeptides (2,5-dioxopiperazines)
  作者：Hans R. Kricheldorf

  DOI：10.1002/mrc.1270130111

  日期：1980.1

  AbstractVarious cyclodipeptides containing glycine, alanine, leucine, valine, phenylalanine, phenylglycine and sarcosine units were synthesized by cyclization of dipeptide pentachlorophenyl esters. The 13C and natural abundance 15N NMR spectra of these heterocycles were measured in trifluoroacetic acid and compared with the spectra of the corresponding amino acids and polypeptides. The 13C NMR carbonyl signals of all cyclodipeptides show a 1.5–4.0 ppm upfield shift relative to the corresponding polypeptides. The 15N NMR signals show no such consistent relationship. The substituent effects and the neighbouring residue effects observed in the 15N NMR spectra of the cyclodipeptides are different from those of polypeptides, while the one bond NH coupling constant of cis and trans amide groups was almost identical. The nitrogen and the carbonyl signal of the Gly units in cyclo‐Gly‐Phe show an extraordinary downfield shift, reflecting the interaction of the phenyl group with the 2,5‐dioxopiperazine ring.