2-bromo-3-[(4-nitrophenyl)methoxy]propionic acid 1,1-dimethylethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-3-[(4-nitrophenyl)methoxy]propionic acid 1,1-dimethylethyl ester
• 英文别名: t-butyl 2-bromo-3-<(4-nitrophenyl)methoxy>propanoate；t-Butyl 2-bromo-3-[(4-nitrophenyl)methoxy]propanoate；tert-butyl 2-bromo-3-[(4-nitrophenyl)methoxy]propanoate
• 化学式: C₁₄H₁₈BrNO₅
• 分子量: 360.205
• InChiKey: KYWDDQMRZVEPJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二乙烯三胺 、 2-bromo-3-[(4-nitrophenyl)methoxy]propionic acid 1,1-dimethylethyl ester 在 氯化钠 、 乙醚 、 水 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以to obtain 12 g of the desired product (0.031 mol)的产率得到N-[2-[(2-aminoethyl)amino]ethyl]-O-[(4-nitrophenyl)methyl]-D,L-serine 1,1-dimethylethyl ester
  参考文献：
  名称：

  Paramagnetic metal icon chelates and use thereof as contrast agents in

  摘要：

  本发明描述了新型顺磁性金属离子螯合物及其作为“磁共振成像”（M.R.I.）诊断技术中胃肠道和特别是肝脏的对比剂的使用。这些新型化合物是由胆酸与螯合剂结合而成，能够螯合二价和三价金属离子。该化合物的化学式为A-L-B，其中A是胆酸及其衍生物的残基，B是具有原子序数20到31、39、42、43、44、49、57到83的二价或三价金属离子的螯合剂残基，L是连接A和B之间的配体。

  公开号：

  US05649537A1
• 作为产物：
  描述：

  对硝基苯甲醇 、 丙烯酸叔丁酯 在 Hg(II) trifluoroacetate 、 溴 、 potassium bromide 作用下， 生成 2-bromo-3-[(4-nitrophenyl)methoxy]propionic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  One-Pot Alkoxymercuriation-Bromodemercuriation: A Versatile Access to 3-Alkoxy-2-bromopropanoic Esters

  摘要：

  A convenient one-pot methodology for the preparation of 3-alkoxy-2-bromopropanoic esters from alkyl acrylates is described. The use of stoichiometric amounts of alkyl acrylate, alcohol and mercury trifluoroacetate in THF makes this procedure versatile and attractive to achieve building blocks for the synthesis of targeted contrast agents for Magnetic Resonance Imaging.

  DOI：

  10.1080/00397919308013793

文献信息

• Paramagnetic metal icon chelates and use thereof as contrast agents in
  申请人：Dibra S.p.A.

  公开号：US05649537A1

  公开（公告）日：1997-07-22

  Novel paramagnetic metal ion chelates and their use as contrast agents in the diagnostic technique known as "magnetic resonance imaging" (M.R.I.) of the gastrointestinal tract and particularly of the liver, are described. The novel compounds result from the conjugation of a bile acid with a chelating agent and are capable of chelating the ions of bivalent and trivalent metals. The compounds have formula A-L-B in which A is the residue of a bile acid and derivatives of a bile acid, B is the residue of a chelating agent of a bivalent or trivalent metal ion having an atomic number of 20 to 31, 39, 42, 43, 44, 49, 57 to 83, L is a ligand between A and B.

  本发明描述了新型顺磁性金属离子螯合物及其作为“磁共振成像”（M.R.I.）诊断技术中胃肠道和特别是肝脏的对比剂的使用。这些新型化合物是由胆酸与螯合剂结合而成，能够螯合二价和三价金属离子。该化合物的化学式为A-L-B，其中A是胆酸及其衍生物的残基，B是具有原子序数20到31、39、42、43、44、49、57到83的二价或三价金属离子的螯合剂残基，L是连接A和B之间的配体。
• BILE ACID CONJUGATES, DERIVATIVES THEREOF WITH METAL COMPLEXES AND RELATED USES
  申请人：BRACCO S.p.A.

  公开号：EP0760683B1

  公开（公告）日：2000-01-05
• US5649537A
  申请人：——

  公开号：US5649537A

  公开（公告）日：1997-07-22
• [EN] BILE ACID CONJUGATES, DERIVATIVES THEREOF WITH METAL COMPLEXES AND RELATED USES<br/>[FR] CONJUGUES D'ACIDE BILIAIRE, LEURS DERIVES FORMES AVEC DES COMPLEXES METALLIQUES ET UTILISATIONS ASSOCIEES
  申请人：BRACCO S.P.A.

  公开号：WO1995032741A1

  公开（公告）日：1995-12-07

  (EN) The invention relates to novel paramagnetic metal ion chelates and their use as contrast agents in the diagnostic technique known as 'magnetic resonance imaging' (M.R.I.).(FR) L'invention se rapporte à de nouveaux chélates d'ions métalliques paramagnétiques, ainsi qu'à leur utilisation comme agents de contraste dans le cadre de la technique diagnostique dite 'imagerie par résonance magnétique' (I.R.M.).
• Conjugates of Gadolinium Complexes to Bile Acids as Hepatocyte-Directed Contrast Agents for Magnetic Resonance Imaging
  作者：Pier Lucio Anelli、Luciano Lattuada、Vito Lorusso、Giovanna Lux、Alberto Morisetti、Pierfrancesco Morosini、Michele Serleti、Fulvio Uggeri

  DOI：10.1021/jm0310683

  日期：2004.7.1

  A series of structurally different Gd(III) conjugates incorporating a bile acid moiety have been prepared. Polyaminopolycarboxylic ligands such as diethylenetriaminepentaacetic acid (DTPA) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid (DOTA) have been selected as chelating subunit for the Gd(III) ion. Cholic acid, cholylglycine, and cholyltaurine have been incorporated as the bile acid moieties. In first generation conjugates the Gd(III) complex is linked to the carboxyl group of cholic acid. Second generation conjugates feature the attachment of the Gd(III) complex to the 3 position of the steroidic backbone of the bile acid. Finally, in third generation conjugates the Gd(III) complex is attached to the E nitrogen atom of cholyllysine. The conjugates are eliminated through the biliary route to a various extent (7.5 to 77% in rats) according to their structural features. Among the most promising terms, a second generation conjugate in which the Gd(III) complex is linked to cholic acid through the 3alpha hydroxy group seems to enter hepatocytes using the Na+/taurocholate transporter. Noticeably, some of the second generation conjugates are characterized by very high tolerabilities (LD50 up to 9.5 mmol/kg) after intravenous administration in mice.