9-[1-(2-methoxycarbonyl-4-amino)phenyl]-6-methoxy-3H-xanthen-3-one | 181213-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-[1-(2-methoxycarbonyl-4-amino)phenyl]-6-methoxy-3H-xanthen-3-one
• 英文别名: Methyl 5-amino-2-(3-methoxy-6-oxoxanthen-9-yl)benzoate；methyl 5-amino-2-(3-methoxy-6-oxoxanthen-9-yl)benzoate
• CAS: 181213-36-5
• 化学式: C₂₂H₁₇NO₅
• 分子量: 375.381
• InChiKey: GMPMRXUGPJGXIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-[1-(2-methoxycarbonyl-4-amino)phenyl]-6-methoxy-3H-xanthen-3-one 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 10.0h， 生成 5-((2S,3S)-3-Carboxy-2,3-dihydroxy-propionylamino)-2-(6-methoxy-3-oxo-3H-xanthen-9-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity

  摘要：

  A series of five haptens have been synthesized for use in in vitro selection experiments from combinatorial antibody libraries. Haptens were designed for the recruitment of serine and cysteine protease reaction mechanisms for the cleavage of Phe-Ala and Phe-Phe (L,L) dipeptide analogues. For the selection of transition state stabilization, Phe(P)(O)Ala (7) and PheP(O)Phe (10) derivatives were synthesized using the Mitsunobu approach where Phe(P) represents the phosphonic acid analogue of phenylalanine and (O)Phe and (O)Ala represent (L)-beta-phenyllactic and (L)-lactic acid, respectively. Optically pure peptidyl diazomethyl ketones 16 and 22 were synthesized for selection of the catalytic ensemble of cysteine proteases. An optically pure dipeptidyl boronic acid 26 was synthesized for the selection of the catalytic ensemble of serine proteases. A strategy for the evolution of catalytic antibodies using these haptens was developed which includes mechanism-based selections. Since mechanism based selections result in covalent trapping of species from libraries, diol and disulfide containing haptenic linkers were developed for the oxidative or reductive release of selected catalysts. Copyright 1O 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00085-5
• 作为产物：
  描述：

  5-aminofluorescein 在 硫酸 、 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 17.0h， 生成 9-[1-(2-methoxycarbonyl-4-amino)phenyl]-6-methoxy-3H-xanthen-3-one
  参考文献：
  名称：

  通过光致电子转移调节荧光素探针荧光特性的合理设计原则

  摘要：

  基于荧光素的探针的荧光特性显示出通过光诱导电子从苯甲酸部分（电子供体）到呫吨部分（电子受体荧光团）的单线激发态的速率进行精细控制。在激光闪光光解实验中观察到，由于电子供体部分的自由基阳离子和呫吨部分的自由基阴离子，瞬态吸收光谱显示谱带清楚地证明了光致电子转移的发生。光致电子转移率和反向电子转移率遵循电子转移率对驱动力的马库斯抛物线依赖性。

  DOI：

  10.1021/ja035282s

文献信息

• Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity
  作者：Jürgen Wagner、Richard A. Lerner、Carlos F. Barbas

  DOI：10.1016/0968-0896(96)00085-5

  日期：1996.6

  A series of five haptens have been synthesized for use in in vitro selection experiments from combinatorial antibody libraries. Haptens were designed for the recruitment of serine and cysteine protease reaction mechanisms for the cleavage of Phe-Ala and Phe-Phe (L,L) dipeptide analogues. For the selection of transition state stabilization, Phe(P)(O)Ala (7) and PheP(O)Phe (10) derivatives were synthesized using the Mitsunobu approach where Phe(P) represents the phosphonic acid analogue of phenylalanine and (O)Phe and (O)Ala represent (L)-beta-phenyllactic and (L)-lactic acid, respectively. Optically pure peptidyl diazomethyl ketones 16 and 22 were synthesized for selection of the catalytic ensemble of cysteine proteases. An optically pure dipeptidyl boronic acid 26 was synthesized for the selection of the catalytic ensemble of serine proteases. A strategy for the evolution of catalytic antibodies using these haptens was developed which includes mechanism-based selections. Since mechanism based selections result in covalent trapping of species from libraries, diol and disulfide containing haptenic linkers were developed for the oxidative or reductive release of selected catalysts. Copyright 1O 1996 Elsevier Science Ltd
• Rational Design Principle for Modulating Fluorescence Properties of Fluorescein-Based Probes by Photoinduced Electron Transfer
  作者：Tetsuo Miura、Yasuteru Urano、Kumi Tanaka、Tetsuo Nagano、Kei Ohkubo、Shunichi Fukuzumi

  DOI：10.1021/ja035282s

  日期：2003.7.1

  to be finely controlled by the rate of photoinduced electron transfer from the benzoic acid moiety (electron donor) to the singlet excited state of the xanthene moiety (electron acceptor fluorophore). The occurrence of photoinduced electron transfer is clearly evidenced by transient absorption spectra showing bands due to the radical cation of the electron donor moiety and the radical anion of the xanthene

  基于荧光素的探针的荧光特性显示出通过光诱导电子从苯甲酸部分（电子供体）到呫吨部分（电子受体荧光团）的单线激发态的速率进行精细控制。在激光闪光光解实验中观察到，由于电子供体部分的自由基阳离子和呫吨部分的自由基阴离子，瞬态吸收光谱显示谱带清楚地证明了光致电子转移的发生。光致电子转移率和反向电子转移率遵循电子转移率对驱动力的马库斯抛物线依赖性。