4-氨基-3-巯基-苯乙酸 | 30132-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 中文名称: 4-氨基-3-巯基-苯乙酸
• 英文名称: 4-amino-3-mercapto-benzeneacetic acid
• 英文别名: 2-amino-6-mercaptobenzene acetic acid；4-Amino-3-mercaptobenzeneacetic acid；2-(4-amino-3-sulfanylphenyl)acetic acid
• CAS: 30132-16-2
• 化学式: C₈H₉NO₂S
• 分子量: 183.231
• InChiKey: DTWSPPRVOMIVOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  395.3±27.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氨基-3-巯基-苯乙酸 在 盐酸 、 ammonium hydroxide 、 氢溴酸 、 溶剂黄146 作用下， 以 乙二醇 为溶剂， 反应 29.0h， 生成 2-[2-(溴甲基)-1,3-苯并噻唑-6-基]乙酸
  参考文献：
  名称：

  抗[2.2]（2,6）苯并噻唑啉酮的合成：[2.2]苯并稠合异氰酸酯的第一个实例

  摘要：

  通过双内酯7的光脱羧作用描述了第一个[2.2]苯并稠合的异氰酸酯8的合成。动态1 H NMR研究表明8在NMR时间尺度上具有构象刚性，而7在构象上可移动。

  DOI：

  10.1016/s0040-4039(97)00909-x
• 作为产物：
  描述：

  (2-氨基苯并噻唑-6-基)乙酸 在 盐酸 、 氢氧化钾 作用下， 生成 4-氨基-3-巯基-苯乙酸
  参考文献：
  名称：

  抗[2.2]（2,6）苯并噻唑啉酮的合成：[2.2]苯并稠合异氰酸酯的第一个实例

  摘要：

  通过双内酯7的光脱羧作用描述了第一个[2.2]苯并稠合的异氰酸酯8的合成。动态1 H NMR研究表明8在NMR时间尺度上具有构象刚性，而7在构象上可移动。

  DOI：

  10.1016/s0040-4039(97)00909-x

文献信息

• ATTEMPT TOWARDS SYN-BENZOTHIAZOLOPHANE: SYNTHESIS AND CONFORMATIONAL STUDY OF SYN-DITHIA-[3.3](2,6) BENZOTHIAZOLOPHANE
  作者：Sabir Η Mashraqui、Sukeerthi Kumar、Kishore R. Nivalkar

  DOI：10.1515/hc.2001.7.1.73

  日期：2001.1
• Synthesis, molecular structure and optical spectral studies of syn-dithia benzothiazolophane and anti-bis-lactone benzothiazolophane
  作者：Sabir H Mashraqui、Sukeerthi Kumar、Elise Trân Huu Dâu

  DOI：10.1016/j.molstruc.2004.04.014

  日期：2004.7

  Synthesis of syn-dithia-benzothiazolophane 1 and anti-bis-lactone benzothiazolophane 2 has been carried out by well established protocols as outlined in Schemes 1 and 2, respectively. The H-1 NMR spectra of heterophanes 1 and 2 were found to be temperature independent in the range of -55 to +120 degreesC which indicates conformationally mobile nature of these molecules. In comparison to plain CHCl3, the UV-visible spectra of 1 and 2 measured in CHCl3 containing trifluoroacetic acid (TFAA) exhibited bathochromic shifts by 25 and 19 nm, respectively. The red shifts are attributed to the increased charge transfer interaction arising from the donor phenyl ring to the acceptor benzothiazolium ring. The emission spectra of thia-bridged 1, both in the neutral as well as the protonated forms are accompanied by large Stokes shifts (Deltanu = 127-156 nm) with the emissions most likely originating from the locally excited states. The bis-lactone 2 in neutral CHCl3 solvent also exhibited a single locally excited emission, but with a relatively lower Stokes shift (Deltanu = 69 nm). Interestingly, unlike 1, bis-lactone 2 in the protonated form displayed both local as well as what appears to be an intramolecular charge transfer emission. The emission behavior of 1 and 2 has been tentatively rationalized on the basis of HOMO-LUMO interaction. Molecular modelling of 1 and 2 generated five reasonable conformations within 5 kcal/mol depending upon the orientation of the benzothiazole rings and the heteroatoms in the connecting bridges. The transannular distances in 1 and 2 were found to be ca. 2.8 and 3.6 Angstrom, respectively. While the rings in 2 are nearly planar, however, in the case of 1 the stacks are slightly curved signifying molecular strain in the letter system. Based on dynamic H-1 NMR spectral analysis and molecular modelling, we propose that these molecules exist as a rapidly equilibrating mixtures of conformers. (C) 2004 Published by Elsevier B.V.
• Synthesis of anti -[2.2] (2,6) benzothiazolophane: The first example of [2.2]benzofused heterophane
  作者：Sabir.H. Mashraqui、Kishor.R. Nivalkar

  DOI：10.1016/s0040-4039(97)00909-x

  日期：1997.6

  Synthesis of the first [2.2] benzofused heterophane 8 is described via photodecarboxylation of bislactone 7. Dynamic 1H NMR studies suggest that 8 is conformationally rigid whereas 7 is conformationally mobile on the NMR time scale.

  通过双内酯7的光脱羧作用描述了第一个[2.2]苯并稠合的异氰酸酯8的合成。动态1 H NMR研究表明8在NMR时间尺度上具有构象刚性，而7在构象上可移动。