<3-(Benzyloxy)-4-methoxyphenyl>propionic acid benzyl ester | 159749-96-9

• 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: <3-(Benzyloxy)-4-methoxyphenyl>propionic acid benzyl ester
• 英文别名: Benzyl 3-(4-methoxy-3-phenylmethoxyphenyl)propanoate
• CAS: 159749-96-9
• 化学式: C₂₄H₂₄O₄
• 分子量: 376.452
• InChiKey: IISPXJAAWSKCDD-UHFFFAOYSA-N

物化性质

• 沸点：
  509.4±45.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <3-(Benzyloxy)-4-methoxyphenyl>propionic acid benzyl ester 在 氢氧化钾 、 lithium hydroxide 、 正丁基锂 、 2,4,6-三异丙基苯磺酰叠氮化物 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 9.45h， 生成 (S)-2-Azido-3-<3-(benzyloxy)-4-methoxyphenyl>propionic acid
  参考文献：
  名称：

  A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis

  摘要：

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.

  DOI：

  10.1021/jo00088a009
• 作为产物：
  描述：

  3-羟基-4-甲氧基肉桂酸 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 丙酮 、 乙腈 为溶剂， 反应 30.0h， 生成 <3-(Benzyloxy)-4-methoxyphenyl>propionic acid benzyl ester
  参考文献：
  名称：

  8,9-Methylenedioxybenzo[i]phenanthridines

  摘要：

  Substituted benzo[i]phenanthridines that have incorporated within their structure an 8,9-methylenedioxy group can exhibit topoisornerase I-targeting activity. Structure-activity studies were performed to examine the influence of saturation at the 11,12-positions of several substituted 8,9-methylenedioxybenzo[i]phenanthridines. The activities of these dihydro analogues were compared to those of their unsaturated analogues. In addition, the influence of varying substituents at the 2- and 3-positions within the A-ring of these 8,9-methylenedioxybenzo[i]phenanthridines on their relative potency as topoisomerase I-targeting agents and cell proliferation as determined using the MTT assay was investigated. 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and its 11,12-dihydro derivative were among the more potent analogues evaluated with regard to topoisomerase I-targeting activity and cytotoxicity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00394-8

文献信息

• A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis
  作者：Anthony J. Pearson、Kieseung Lee

  DOI：10.1021/jo00088a009

  日期：1994.5

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.
• 8,9-Methylenedioxybenzo[i]phenanthridines
  作者：Dajie Li、Baoping Zhao、Sai-Peng Sim、Tsai-Kun Li、Angela Liu、Leroy F Liu、Edmond J LaVoie

  DOI：10.1016/s0968-0896(03)00394-8

  日期：2003.8

  Substituted benzo[i]phenanthridines that have incorporated within their structure an 8,9-methylenedioxy group can exhibit topoisornerase I-targeting activity. Structure-activity studies were performed to examine the influence of saturation at the 11,12-positions of several substituted 8,9-methylenedioxybenzo[i]phenanthridines. The activities of these dihydro analogues were compared to those of their unsaturated analogues. In addition, the influence of varying substituents at the 2- and 3-positions within the A-ring of these 8,9-methylenedioxybenzo[i]phenanthridines on their relative potency as topoisomerase I-targeting agents and cell proliferation as determined using the MTT assay was investigated. 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and its 11,12-dihydro derivative were among the more potent analogues evaluated with regard to topoisomerase I-targeting activity and cytotoxicity. (C) 2003 Elsevier Ltd. All rights reserved.