ethyl 4-(3-carboxypropyl)-6-dibenzofuranpropionate | 137959-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl 4-(3-carboxypropyl)-6-dibenzofuranpropionate
• 英文别名: 3-[6-(3-Ethoxy-3-oxopropyl)dibenzofuran-4-yl]propanoic acid
• CAS: 137959-95-6
• 化学式: C₂₀H₂₀O₅
• 分子量: 340.376
• InChiKey: HEIMNODRDYFGCB-UHFFFAOYSA-N

物化性质

• 沸点：
  521.2±40.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(3-carboxypropyl)-6-dibenzofuranpropionate 在 sodium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 40.0h， 生成 4-(N-tert-butyloxycarbonyl-2-aminoethyl)-6-dibenzofuranpentafluorophenylpropionate
  参考文献：
  名称：

  Tsang, Kwok Yin; Diaz, Humberto; Graciani, Nilsa, Journal of the American Chemical Society, 1994, vol. 116, # 9, p. 3988 - 4005

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯并呋喃 在 palladium on activated charcoal sodium hydroxide 、 四甲基乙二胺 、 3 A molecular sieve 、 氢气 、 碘 、 仲丁基锂 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0~95.0 ℃ 、379.21 kPa 条件下， 反应 92.5h， 生成 ethyl 4-(3-carboxypropyl)-6-dibenzofuranpropionate
  参考文献：
  名称：

  Tsang, Kwok Yin; Diaz, Humberto; Graciani, Nilsa, Journal of the American Chemical Society, 1994, vol. 116, # 9, p. 3988 - 4005

  摘要：

  DOI：

文献信息

• The synthesis of dibenzofuran based diacids and amino acids designed to nucleate parallel and antiparallel β-sheet formation.
  作者：Humberto Diaz、Jeffery W. Kelly

  DOI：10.1016/s0040-4039(00)93540-8

  日期：1991.10

  4-(N-tert-butyloxycarbonyl-2-aminoethyl-)-6-dibenzofuranpropionic acid (1) and 4,6-dibenzofurandipropionic acid (2) designed to nucleate antiparallel and parallel beta-sheet formation, respectively, have been synthesized in multi-gram quantities.
• Improved Synthesis of the Boc and Fmoc Derivatives of 4-(2‘-Aminoethyl)-6-dibenzofuranpropionic Acid:  An Unnatural Amino Acid That Nucleates β-Sheet Folding
  作者：Haimanot Bekele、Carey L. Nesloney、Kurt W. McWilliams、Niki M. Zacharias、Penchit Chitnumsub、Jeffery W. Kelly

  DOI：10.1021/jo961063w

  日期：1997.4.1
• The nucleation of monomeric parallel β-sheet-like structures and their self-assembly in aqueous solution
  作者：Penchit Chitnumsub、Wayne R. Fiori、Hilal A. Lashuel、Humberto Diaz、Jeffery W. Kelly

  DOI：10.1016/s0968-0896(98)00222-3

  日期：1999.1

  The aromatic diacid residue 4,6-dibenzofuranbispropionic acid (1) was designed to nucleate a parallel beta-sheet-like structure in small peptides in aqueous solution via a hydrogen-bonded hydrophobic cluster. Even though a 14-membered ring hydrogen bond necessary for parallel beta-sheet formation is favored in simple amides composed of 1, this hydrogen bonding interaction does not appear to be sufficient to nucleate parallel beta-sheet formation in the absence of hydrophobic clustering between the dibenzofuran portion of 1 and the hydrophobic side chains of the flanking alpha-amino acids. The subsequence --hydrophobic residue-1-hydrophobic residue-- is required for folding in the context of a nucleated two-stranded parallel beta-sheet structure. In all cases where the peptidomimetics can fold into two diastereomeric parallel beta-sheet structures having different hydrogen bonding networks, these conformations appear to exchange rapidly. The majority of the parallel beta-sheet structures evaluated herein undergo linked intramolecular folding and self-assembly, affording a fibrillar beta-sheet quaternary structure. To unlink folding and assembly, asymmetric parallel beta-sheet structures incorporating N-methylated alpha-amino acid residues have been synthesized using a new solid phase approach. Residue 1 facilitates the folding of several peptides described within affording a monomeric parallel beta-sheet-like structure in aqueous solution, as ascertained by a variety of spectroscopic and biophysical methods, increasing our understanding of parallel beta-sheet structure.
• US7339023B2
  申请人：——

  公开号：US7339023B2

  公开（公告）日：2008-03-04
• Tsang, Kwok Yin; Diaz, Humberto; Graciani, Nilsa, Journal of the American Chemical Society, 1994, vol. 116, # 9, p. 3988 - 4005
  作者：Tsang, Kwok Yin、Diaz, Humberto、Graciani, Nilsa、Kelly, Jeffery W.

  DOI：——

  日期：——