(2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid | 131613-02-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid
• 英文别名: (2S,3R)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoic acid
• CAS: 131613-02-0
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: KHQWPNQLSKDWAR-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.78
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid 反应 11.0h， 以68%的产率得到地尔硫卓杂质4
  参考文献：
  名称：

  Acs, M.; Gizur, T.; Peter, I., Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 187, p. 289 - 296

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (2S,3R)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoate 生成 (2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• ——
  作者：

  DOI：——

  日期：——
• Enantiomer Associations in the Crystal Structures of Racemic and (2S,3R)-(-)-3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one.
  作者：Karalin Marthi、Sine Larsen、Mária Ács、Zsuzsa Jászay、Elemér Fogassy、Kristian Rønning Pedersen、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0906

  日期：——

  The crystal structures of racemic and (2S,3R)-(-)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (C16H15NO3S) have been determined in order to compare the interactions between molecules of the same and opposite chirality. The enantiomeric associations observed in these two crystal structures are analysed, relating the differences to those found in the equivalent diastereomers, (2R,3R) and/or (2S,3S). Single-crystal X-ray diffraction data were collected at low temperature with Cu K alpha radiation (lambda = 1.54184 Angstrom). Optically active: monoclinic, space group C2, with a = 24.726(3), b = 5.2426(5), c = 12.0726(12) Angstrom, beta = 112.979(9)degrees, V = 1440.8(5) Angstrom(3), Z = 4, D-x = 1.389 g cm(-3), mu = 20.35 cm(-1), the refinement on 2918 observed reflections gave R = 0.0271. Racemic: monoclinic, space group P2(1)/n, with a = 13.308(3), b = 4.8474(8), c = 22.130(4) Angstrom, beta = 91.782(14), V = 1426.9(5) Angstrom(3), Z = 4, D-x = 1.403 g cm(-3), mu = 20.54 cm(-1), refined to R = 0.0318 for 2753 observed reflections. An intramolecular hydrogen bond between the hydroxy and carbonyl groups appears to stabilize the benzothiazepinone ring in the (P,2S,3R) boat conformation with the hydroxy and methoxyphenyl substituents in equatorial positions. In both crystal structures two N-H ... O hydrogen bonds connect the molecules into dimers. In the optically active compound the two molecules are related by a twofold axis, in the racemate by an inversion centre. The racemate contains an additional hydrogen bond which is reflected by its higher melting enthalpy compared with the optically active compound. The difference in the chiral discrimination in the solutions of the cis-and trans-diastereomers does not appear to have its origin in the strong (O-H ... O, N-H ... O) hydrogen bonds, but rather in the weak (C-H ... O) interactions.
• HASHIYAMA, TOMIKI;INOUE, HIROZUMI;KONDA, MIKIHIKO;TAKEDA, MIKIO, J. CHEM. SOC. PERKIN TRANS., 1984, N 8, 1725-1732
  作者：HASHIYAMA, TOMIKI、INOUE, HIROZUMI、KONDA, MIKIHIKO、TAKEDA, MIKIO

  DOI：——

  日期：——
• Acs, M.; Gizur, T.; Peter, I., Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 187, p. 289 - 296
  作者：Acs, M.、Gizur, T.、Peter, I.、Harsanyi, K.、Jaszay, Zs.、Fogassy, E.

  DOI：——

  日期：——