N-(benzyloxycarbonyl)-β-alanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl)methyl ester | 1093125-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: N-(benzyloxycarbonyl)-β-alanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl)methyl ester
• 英文别名: N-(benzyloxycarbonyl)-β-alanine (9-methoxy-(5,6)-benzocoumarin-1-yl)methyl ester；(9-Methoxy-3-oxobenzo[f]chromen-1-yl)methyl 3-(phenylmethoxycarbonylamino)propanoate；(9-methoxy-3-oxobenzo[f]chromen-1-yl)methyl 3-(phenylmethoxycarbonylamino)propanoate
• CAS: 1093125-18-8
• 化学式: C₂₆H₂₃NO₇
• 分子量: 461.471
• InChiKey: VRJBZMPOTQXTAG-UHFFFAOYSA-N

物化性质

• 熔点：
  121.4-123.0 °C
• 沸点：
  691.3±55.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-β-alanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl)methyl ester 以 甲醇 为溶剂， 反应 8.55h， 生成 N-CBZ-beta-丙氨酸
  参考文献：
  名称：

  2-Oxo-2 H-苯并[h]苯并吡喃为神经递质氨基酸的新光敏保护基

  摘要：

  为了开发新的基于苯并吡喃基的光可裂解保护基，设计了带有甲氧基取代基的新型氯甲基化和羟甲基化的2-氧代-2 H-苯并[ h ]苯并吡喃衍生物，并将其用于一系列荧光生物共轭物的合成。通过酯或氨基甲酸酯键与几种模型神经递质氨基酸（甘氨酸，丙氨酸，β-丙氨酸和γ-氨基丁酸，GABA）结合。将得到的具有可见光发射和高荧光量子产率的荧光生物共轭物，在甲醇/ HEPES缓冲液（80:20）溶液中，在不同的照射波长（250、300、350和419 nm）下进行光裂解反应，并进行光裂解动力学分析。获得数据。

  DOI：

  10.1007/s00726-009-0383-z
• 作为产物：
  描述：

  1-chloromethyl-9-methoxy-3-oxo-3H-benzo[f]benzopyran 、 N-CBZ-beta-丙氨酸 在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到N-(benzyloxycarbonyl)-β-alanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl)methyl ester
  参考文献：
  名称：

  Neurotransmitter amino acid—oxobenzo[f]benzopyran conjugates: synthesis and photorelease studies

  摘要：

  A series of fluorescent conjugates of neurotransmitter amino acids, such as P-alanine, tyrosine, 3,4-dihydroxyplienylalanine (DOPA) and glutamic acid, were prepared by reaction with a suitable fluorophore, namely 1-chloromethyl-9-methoxy-3-oxo-3H-benzo[f]benzopyran. The photophysical properties of the resulting ester bioconjugates were evaluated as well as the stability to photolysis at different wavelengths of irradiation (250, 300, 350 and 419 nm). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.050

文献信息

• Phototriggering of neuroactive amino acids from 5,6-benzocoumarinyl conjugates
  作者：Maria José G. Fernandes、Susana P.G. Costa、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tet.2011.01.090

  日期：2011.4

  Uncaging of several neuroactive amino acids, namely beta-alanine, tyrosine, 3,4-dihydroxyphenylalanine (DOPA) and glutamic acid from the corresponding 5,6-benzocoumarinyl conjugates was carried out by irradiation at different wavelengths and in different solvent systems. The release of the various amino acids was faster in ACN/HEPES buffer mixtures and for the tyrosine conjugate, an increase in the photolysis reaction rates and the quantitative uncaging of the amino acid was associated with increasing water content in the solvent mixture. (C) 2011 Elsevier Ltd. All rights reserved.
• 2-Oxo-2H-benzo[h]benzopyran as a new light sensitive protecting group for neurotransmitter amino acids
  作者：Ana M. S. Soares、Susana P. G. Costa、M. Sameiro T. Gonçalves

  DOI：10.1007/s00726-009-0383-z

  日期：2010.6

  Aiming at the development of new benzopyran-based photocleavable protecting groups, novel chloromethylated and hydroxymethylated 2-oxo-2H-benzo[h]benzopyran derivatives bearing a methoxy substituent were designed and used in the synthesis of a series of fluorescent bioconjugates, by linking through an ester or urethane bond to several model neurotransmitter amino acids (glycine, alanine, β-alanine

  为了开发新的基于苯并吡喃基的光可裂解保护基，设计了带有甲氧基取代基的新型氯甲基化和羟甲基化的2-氧代-2 H-苯并[ h ]苯并吡喃衍生物，并将其用于一系列荧光生物共轭物的合成。通过酯或氨基甲酸酯键与几种模型神经递质氨基酸（甘氨酸，丙氨酸，β-丙氨酸和γ-氨基丁酸，GABA）结合。将得到的具有可见光发射和高荧光量子产率的荧光生物共轭物，在甲醇/ HEPES缓冲液（80:20）溶液中，在不同的照射波长（250、300、350和419 nm）下进行光裂解反应，并进行光裂解动力学分析。获得数据。
• Neurotransmitter amino acid—oxobenzo[f]benzopyran conjugates: synthesis and photorelease studies
  作者：Maria J.G. Fernandes、M. Sameiro T. Gonçalves、Susana P.G. Costa

  DOI：10.1016/j.tet.2008.09.050

  日期：2008.12

  A series of fluorescent conjugates of neurotransmitter amino acids, such as P-alanine, tyrosine, 3,4-dihydroxyplienylalanine (DOPA) and glutamic acid, were prepared by reaction with a suitable fluorophore, namely 1-chloromethyl-9-methoxy-3-oxo-3H-benzo[f]benzopyran. The photophysical properties of the resulting ester bioconjugates were evaluated as well as the stability to photolysis at different wavelengths of irradiation (250, 300, 350 and 419 nm). (C) 2008 Elsevier Ltd. All rights reserved.