(2RS,4R)-thiazolidine-2,4-dicarboxylic acid | 201942-91-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2RS,4R)-thiazolidine-2,4-dicarboxylic acid
• 英文别名: thiazolidine-2,4-dicarboxylic acid；(4R)-thiazolidine-2,4-dicarboxylic acid；thiazolidine 2,4-dicaboxylic acid；(2Ξ,4R)-thiazolidine-2,4-dicarboxylic acid；N,S-carboxymethanediyl-L-cysteine；(2Ξ,4R)-Thiazolidin-2,4-dicarbonsaeure；(4R)-1,3-thiazolidine-2,4-dicarboxylic acid
• CAS: 201942-91-8
• 化学式: C₅H₇NO₄S
• 分子量: 177.181
• InChiKey: DAXBISKSIDBYEU-SCQFTWEKSA-N

物化性质

• 沸点：
  524.3±50.0 °C(Predicted)
• 密度：
  1.629±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2RS,4R)-thiazolidine-2,4-dicarboxylic acid 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (3R,7aR)-7-Oxo-6-phenyl-5-thioxo-tetrahydro-imidazo[1,5-c]thiazole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  手性1,3-噻唑烷-2,4-二羧酸的非对映体和区域异构双环硫氢化

  摘要：

  通过使（1R，3-噻唑烷-2,4-二羧酸或其二甲基二酯的（2 R）/（2 S）-非对映异构体混合物与PhNCS反应，以立体选择的方式合成双环巯基乙内酰脲。与PhNCS的5,5-二甲基-1,3-噻唑烷-2,4-二羧酸导致环化反应涉及噻唑烷环C（2）中心的CO基团，而酸的二甲基二酯使环化反应涉及CO组在C（4）。相反，涉及未取代的1,3-噻唑烷-2,4-二羧酸或其二甲基二酯的反应会导致巯基乙内酰脲，其中仅在C（4）处的COO基团发生闭环。与开环方向无关，所有反应仅产生具有（R）-C（2）处的配置。构型分配基于1 H-和13 C-NMR研究，并通过X射线晶体学分析得到证实。

  DOI：

  10.1002/hlca.19980810324
• 作为产物：
  描述：

  L-半胱氨酸盐酸盐无水物 、 2,2-二乙氧基乙酸乙酯 在 水 作用下， 生成 (2RS,4R)-thiazolidine-2,4-dicarboxylic acid
  参考文献：
  名称：

  Cook; Heilbron, Chemistry of Penicillin

  摘要：

  DOI：

文献信息

• New Dipeptides Containing Thiazolidine-4-carboxylic Acid Derivatives: Synthesis and Characterization Using NMR Techniques and X-Ray Data.
  作者：Nadia PELLEGRINI、Bernard REFOUVELET、Gregorio CRINI、Olivier BLACQUE、Marek M. KUBICKI、Jean-Francois ROBERT

  DOI：10.1248/cpb.47.950

  日期：——

  New dipeptides, structural analogues of known immunomodulating agents, were prepared by stereospecific condensation between 2-substituted thiazolidine-4-carboxylate esters with N-substituted L-proline or L-thiaproline. The structure of these compounds has been elucidated by combination of NMR methods and X-ray analysis. In addition, NMR measurements on dipeptides indicated the presence of S-cis and S-trans conformers around the amide bonds.

  新二肽是已知免疫调节剂的结构类似物，通过立体特异性缩合2-取代的噻唑烷-4-羧酸酯与N-取代的L-脯氨酸或L-硫代脯氨酸制备。这些化合物的结构已通过NMR方法和X射线分析相结合得以阐明。此外，对二肽的NMR测量表明了在酰胺键周围存在S-顺式和S-反式构象体。
• Cysteine derivative
  申请人：AJINOMOTO CO., INC.

  公开号：US09212154B2

  公开（公告）日：2015-12-15

  Cysteine compounds represented by the following formula wherein each symbol is as defined in the specification, and salts thereof, are superior in stability, have less odor, exhibit an eumelanin production suppressive effect, and are useful as cosmetic agents.

  以下公式所代表的半胱氨酸化合物，其中每个符号如规范中定义，并其盐，具有更好的稳定性，气味较轻，表现出对黑色素产生抑制作用，并可用作化妆品剂。
• Fourneau,J.-P. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 272, p. 1515 - 1517
  作者：Fourneau,J.-P. et al.

  DOI：——

  日期：——
• Synthesis and Chirality Control of Bulk Crystals and Nanocrystals: From a Right-Handed Nonpolar Chain to a Left-Handed Polar Chain
  作者：Yan-Yan Yin、Yan-Li Zhao、Jian-Gong Ma、Xiao-Chang Cao、Peng Cheng

  DOI：10.1021/ic302711b

  日期：2013.4.1

  Both bulk crystals and nanocrystals of two helical complexes, [Cu(mu(2)center dot L)(H2O)](n) (1) and [Cu(mu(2)-L)(H2O)]center dot 2H(2)O}(n) (2) (H2L = thiazolidine-2,4-dicarboxylic acid), have been synthesized with the chiralities of right-handedness (1) and left-handedness (2), respectively. 4-Cyanopyridine and poly(vinylpyrrolidone) (PVP) have been applied to control the synthesis of complexes with different helicities in bulk-crystal and nanocrystal forms, respectively. 2 can be irreversibly transformed to 1 under heating. Associated with the conformation changing, the symmetry alters between nonpolar and polar space groups.
• Chiral Ni(II) Coordination Polymers: Structure-Driven Effects of Temperature and Polyvinylpyrrolidone
  作者：Yan-Yan Yin、Jian-Gong Ma、Zheng Niu、Xiao-Chang Cao、Wei Shi、Peng Cheng

  DOI：10.1021/ic300106k

  日期：2012.4.16

  Chiral Ni(II) coordination compounds with structures of [NiL(H2O)(3)] (1) and [NiL(H2O)]center dot 0.5H(2)O}(n) (2) (H2L = thiazolidine 2,4-dicaboxlic acid) have been successfully synthesized by the reaction of Ni(CH3COO)(2)center dot 4H(2)O and H2L in aqueous solution at 25 and 80 degrees C, respectively. From the same procedure with polyvinylpyrrolidone (PVP) as a surfactant, another corresponding micrometer-scale Ni(II) coordination polymer, [NiL(H2O)(2)]center dot H2O}(n) (3), has been obtained at both 25 and 80 degrees C, which shows a different structure (one-dimensional, ID) than both 1 (discrete molecule) and 2 (3D). The conversions of structures and conformations are directed by temperature and surfactant (PVP), as confirmed by powder and single-crystal X-ray diffraction. Circular Dichroism (CD) and Second Harmonic Generation (SHG) measurements of the products have been investigated as well; which indicate the potential applications of these products in chiral and nonlinear optical (NLO) areas.