methyl 4,7-dioxoheptanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 4,7-dioxoheptanoate
• 英文别名: 4,7-dioxo-heptanoic acid methyl ester；DOHA-Me
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: APZLAOXHFRIBJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4,7-dioxoheptanoate 、 N-生物素基-1,6-己烷二胺 以 甲醇 为溶剂， 反应 9.0h， 以75%的产率得到3-(1-{6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexyl}-1H-pyrrol-2-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and structural characterization of carboxyethylpyrrole-modified proteins: mediators of age-related macular degeneration

  摘要：

  Protein modifications in which the e-amino group of lysyl residues is incorporated into a 2-(omega-carboxy-ethyl)pyrrole (CEP) are mediators of age-related macular degeneration (AMD). They promote both angiogenesis into the retina ('wet AMD') and geographic retinal atrophy ('dry AMD'). Blood levels of CEPs are biomarkers for clinical prognosis of the disease. To enable mechanistic studies of their role in promoting AMD, for example, through the activation of B- and T-cells, interaction with receptors, or binding with complement proteins, we developed an efficient synthesis of CEP derivatives, that is especially effective for proteins. The structures of tryptic peptides derived from CEP-modified proteins were also determined. A key finding is that 4,7-dioxoheptanoic acid 9-fluorenylmethyl ester reacts with primary amines to provide 9-fluorenylmethyl esters of CEP-modified proteins that can be deprotected in situ with 1,8-diazabicyclo[5.4.0]undec-7-ene without causing protein denaturation. The introduction of multiple CEP-modifications with a wide variety of CEP: protein ratios is readily achieved using this strategy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.009
• 作为产物：
  描述：

  methyl 5-diazo-4-oxopentanoate 在 盐酸 、 铜 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 4,7-dioxoheptanoate
  参考文献：
  名称：

  Wenkert, Ernest; Bakuzis, Marinalva, L. F.; Buckwalter, Brian L., Synthetic Communications, 1981, vol. 11, # 7, p. 533 - 544

  摘要：

  DOI：

文献信息

• Flavouring composition containing gamma-jasmolactone, the use of such a flavouring composition or gamma-jasmolactone per se for flavouring foodstuffs as well as the flavoured foodstuffs obtained
  申请人：QUEST INTERNATIONAL B.V.

  公开号：EP0473842A1

  公开（公告）日：1992-03-11

  The invention relates to flavouring compositions characterized by an effective amount of gamma-jasmolactone having the formula as well as the use of these flavourings or gamma-jasmolactone per se for imparting, enhancing or improving the flavour, in particular the fruity character of foodstuffs and drinks.

  本发明涉及以有效含量的γ-茉莉内酯为特征的调味组合物，其式如下 以及使用这些调味剂或γ-茉莉内酯本身来赋予、增强或改善食品和饮料的风味，特别是果味。
• WENKERT, E.;BAKUZIS, M. L. F.;BUCKWALTER, B. L.;WOODGATE, P. D., SYNTH. COMMUN., 1981, 11, N 7, 533-543
  作者：WENKERT, E.、BAKUZIS, M. L. F.、BUCKWALTER, B. L.、WOODGATE, P. D.

  DOI：——

  日期：——
• JPH03151372A
  申请人：——

  公开号：JPH03151372A

  公开（公告）日：1991-06-27
• US5783244A
  申请人：——

  公开号：US5783244A

  公开（公告）日：1998-07-21
• [EN] CARBOXYETHYLPYRROLE COMPOUNDS AND METHODS OF THEIR PRODUCTION<br/>[FR] COMPOSÉS CARBOXYÉTHYLPYRROLE ET PROCÉDÉS POUR LEUR PRODUCTION
  申请人：CLEVELAND CLINIC FOUNDATION

  公开号：WO2008089487A2

  公开（公告）日：2008-07-24

  [EN] The present invention involves methods of anchoring carboxyethylpyrrole (CEP) haptens to carriers via various linkers. Provided herein are 9-fluorenylmethyl (Fm) masked-CEP-linker acids and Fm masked-CEP-linker esters that are useful for the preparation of CEP-linker- carrier derivatives. Also provided are methods of preparing said Fm masked-CEP-linker acids, Fm masked-CEP-linker esters and CEP-linker-carrier derivatives.
  [FR] La présente invention concerne des procédés d'ancrage d'haptènes de carboxyéthylpyrrole (CEP) à des vecteurs via différents lieurs. L'invention concerne des 9-fluorénylméthyle (Fm) masqué-CEP-acides lieurs et des Fm masqué-CEP-esters lieurs qui sont utiles pour la préparation de dérivés CEP-lieur-vecteur. L'invention concerne également des procédés de préparation desdits Fm masqué-CEP-acides lieurs, desdits Fm masqué-CEP-esters lieurs et desdits dérivés CEP-lieur-vecteur.