(+/-)-(2S,4R)-3-(4-fluorophenylcarbonyl)-2,5,5-trimethylthiazolidine-4-carboxylic acid

• 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: (+/-)-(2S,4R)-3-(4-fluorophenylcarbonyl)-2,5,5-trimethylthiazolidine-4-carboxylic acid
• 英文别名: (2R,4S)-3-(4-fluorobenzoyl)-2,5,5-trimethyl-1,3-thiazolidine-4-carboxylic acid
• 化学式: C₁₄H₁₆FNO₃S
• 分子量: 297.35
• InChiKey: FAPBHVYTABHOSD-KCJUWKMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-(2S,4R)-3-(4-fluorophenylcarbonyl)-2,5,5-trimethylthiazolidine-4-carboxylic acid 、 苯丙炔酸乙酯 在 乙酸酐 作用下， 反应 4.0h， 以67%的产率得到ethyl 1,1,3-trimethyl-5-(4-fluorophenyl)-7-phenyl-1H,3H-pyrrolo[1,2-c]thiazole-6-carboxylate
  参考文献：
  名称：

  Flash vacuum pyrolysis of 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2-vinyl-1H-pyrroles

  摘要：

  The flash vacuum pyrolysis of new 1,1-dimethyl- and 1-methyl-1H,3H-pyrrolo[1,2-c]thiazole-2,2-dioxides gave penta-substituted 2-vinyl-1H-pyrroles via sigmatropic [1,8]-H shift of the corresponding azafulvenium methide intermediates. In some cases these 1H-pyrroles underwent rearrangement to 2-allyl-1H-pyrroles. Di-substituted 2-vinylpyrroles have also been prepared and their reactivity studied. Under FVP N-benzyl-pyrrol-2-ylpropenoates were converted into 3H-pyrrolizin-3-ones. On the other hand, microwave-assisted reaction of 1-benzyl-2-vinyl-1H-pyrrole gave a 4,5,6,7-tetrahydro-1H-indole derivative. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.079
• 作为产物：
  描述：

  2,5,5-trimethyl-1,3-thiazolidine-4-carboxylic acid 、 对氟苯甲酰氯 在 吡啶 作用下， 反应 3.0h， 以66%的产率得到(+/-)-(2S,4R)-3-(4-fluorophenylcarbonyl)-2,5,5-trimethylthiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Flash vacuum pyrolysis of 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2-vinyl-1H-pyrroles

  摘要：

  The flash vacuum pyrolysis of new 1,1-dimethyl- and 1-methyl-1H,3H-pyrrolo[1,2-c]thiazole-2,2-dioxides gave penta-substituted 2-vinyl-1H-pyrroles via sigmatropic [1,8]-H shift of the corresponding azafulvenium methide intermediates. In some cases these 1H-pyrroles underwent rearrangement to 2-allyl-1H-pyrroles. Di-substituted 2-vinylpyrroles have also been prepared and their reactivity studied. Under FVP N-benzyl-pyrrol-2-ylpropenoates were converted into 3H-pyrrolizin-3-ones. On the other hand, microwave-assisted reaction of 1-benzyl-2-vinyl-1H-pyrrole gave a 4,5,6,7-tetrahydro-1H-indole derivative. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.079

文献信息

• Synthesis and biological evaluation of new naphthoquinone-containing pyrrolo-thiazoles as anticancer agents
  作者：Susana M. M. Lopes、Mafalda Laranjo、Arménio C. Serra、Ana Margarida Abrantes、António M. d'A. Rocha Gonsalves、Maria Filomena Botelho、Ana Matos Beja、Manuela Ramos Silva、Teresa M. V. D. Pinho e Melo

  DOI：10.1002/jhet.396

  日期：——

  Abstract magnified image Naphthoquinones undergo 1,3‐dipolar cycloaddition with bicyclic münchnones generated from thiazolidines affording new pyrrolo‐thiazoles with a fused quinone nucleus. The products were obtained as single enantiomers in good yields. These benzo[f]thiazolo[4,3‐a]isoindole‐6,11(1H,3H)‐diones are comprised of four fused rings and present a very planar structure. The evaluation of their anticancer activity against melanoma A375 and colorectal adenocarcinoma WiDr human cell lines showed only moderate activity but gave insight into the modeling of new structures. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.] J. Heterocyclic Chem., (2010).