(4R) ethyl 2-(4-nitrophenyl)thiazolidine-4-carboxylate | 78979-49-4

• 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: (4R) ethyl 2-(4-nitrophenyl)thiazolidine-4-carboxylate
• 英文别名: ethyl (4R)-2-(4-nitrophenyl)-1,3-thiazolidine-4-carboxylate
• CAS: 78979-49-4
• 化学式: C₁₂H₁₄N₂O₄S
• 分子量: 282.32
• InChiKey: ZHAPKBCTYLNTEZ-VUWPPUDQSA-N

物化性质

• 沸点：
  450.1±45.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R) ethyl 2-(4-nitrophenyl)thiazolidine-4-carboxylate 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 silver carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.0h， 生成 3-[N-(tert-butoxycarbonyl)-L-alanyl]amino-3-ethoxycarbonyl-2,3-dihydrothiopheno[2,3-b]naphthalene-4,9-dione
  参考文献：
  名称：

  New benzo[g]isoquinoline-5,10-diones and dihydrothieno [2,3-b]naphtho-4,9-dione derivatives

  摘要：

  Novel antitumoral agents with quinonic structure were synthesized and evaluated for their in vitro cytotoxic activities. This study examines the cytotoxic activities of several aryl benzo[g]isoquinoline-5,10-dione derivatives and a number of aminoacyl dihydrothieno[2,3-b]naphtho-4.9-dione (DTNQ) derivatives containing amino acids in position 3 of the ring system. Compound 6 showed remarkable cytotoxic activity at submicromolar concentration not only against several human leukaemia and solid tumour cell lines, but also toward sensitive and resistant human cell lines. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00310-9
• 作为产物：
  描述：

  L-半胱氨酸乙酯盐酸盐 、 对硝基苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 以90%的产率得到(4R) ethyl 2-(4-nitrophenyl)thiazolidine-4-carboxylate
  参考文献：
  名称：

  可逆噻唑烷交换：一种适用于动态组合化学的新反应

  摘要：

  使用噻唑烷和芳香醛的可逆氨基硫醇交换反应生成了新的动态组合库 (DCL)。该反应在 pH 4 和室温的水性缓冲介质中进行，以生成热力学控制的杂环混合物。还报道了对映体纯的噻唑烷基恶唑烷的合成。恶唑烷部分可以在催化p- TsOH存在下在 CH 2 Cl 2中交换。

  DOI：

  10.1021/ol901104a

文献信息

• Synthesis of Oxazolidines, Thiazolidines, and 5,6,7,8-Tetrahydro-1<i>H</i>,3<i>H</i>-pyrrolo[1,2-<i>c</i>]oxazole (or thiazole)-1,3-diones from β-Hydroxy- or β-Mercapto-α-amino Acid Esters
  作者：Mahmoud Zarif Amin Badr、Morsy Mohamed Aly、Atiat Mohamed Fahmy、Mansour Esmael Younis Mansour

  DOI：10.1246/bcsj.54.1844

  日期：1981.6

  2-Aryl-4-(ethoxycarbonyl)oxazolidines and thiazolidines (1) were prepared from the corresponding α-amino acid ethyl esters containing either hydroxyl or mercapto groups in the β-position by fusion with some aromatic aldehydes. Dehydrogenation of 1 with N-bromosuccinimide gave the corresponding oxazoles and thiazoles. The oxazolidines and thiazolidines gave Mannich bases on interaction with p-nitrobenzaldehyde

  2-Aryl-4-（乙氧羰基）恶唑烷和噻唑烷 (1) 是由相应的 α-氨基酸乙酯通过与一些芳香醛融合而在 β 位含有羟基或巯基而制备的。1 用 N-溴代琥珀酰亚胺脱氢得到相应的恶唑和噻唑。恶唑烷和噻唑烷通过与对硝基苯甲醛和哌啶的相互作用产生曼尼希碱。1 的乙酰化得到相应的 N-乙酰基衍生物，在无水 ZnCl2 存在下融合发生环化，得到相应的双环化合物 5,6,7,8-四氢-1H,3H-吡咯并[1,2-c]恶唑（或噻唑）-1,3-二酮。
• A practical, green, and selective approach toward the synthesis of pharmacologically important quinone-containing heterocyclic systems using alumina-catalyzed Michael addition reaction
  作者：Sabrina Castellano、Alessia Bertamino、Isabel Gomez-Monterrey、Marisabella Santoriello、Paolo Grieco、Pietro Campiglia、Gianluca Sbardella、Ettore Novellino

  DOI：10.1016/j.tetlet.2007.11.148

  日期：2008.1

  A convenient method for double Michael additions to quinone systems catalyzed by Al2O3, is reported. The advantages of this method include the use of a cheap and environment-friendly catalyst, a straightforward isolation of the pure product by filtration, high yields, and excellent selectivity, thus providing rapid access to useful building blocks for the preparation of biologically active quinones

  报道了一种方便的方法，用于通过Al 2 O 3催化将迈克尔双加成到醌体系中。该方法的优点包括使用便宜且环境友好的催化剂，通过过滤直接分离纯产物，高收率和优异的选择性，从而为制备生物活性醌提供了快速获得有用的结构单元的途径。
• New benzo[g]isoquinoline-5,10-diones and dihydrothieno [2,3-b]naphtho-4,9-dione derivatives
  作者：Isabel Gomez-Monterrey、Pietro Campiglia、Paolo Grieco、Maria Vittoria Diurno、Adele Bolognese、Paolo La Colla、Ettore Novellino

  DOI：10.1016/s0968-0896(03)00310-9

  日期：2003.8

  Novel antitumoral agents with quinonic structure were synthesized and evaluated for their in vitro cytotoxic activities. This study examines the cytotoxic activities of several aryl benzo[g]isoquinoline-5,10-dione derivatives and a number of aminoacyl dihydrothieno[2,3-b]naphtho-4.9-dione (DTNQ) derivatives containing amino acids in position 3 of the ring system. Compound 6 showed remarkable cytotoxic activity at submicromolar concentration not only against several human leukaemia and solid tumour cell lines, but also toward sensitive and resistant human cell lines. (C) 2003 Elsevier Ltd. All rights reserved.
• Reversible Thiazolidine Exchange: A New Reaction Suitable for Dynamic Combinatorial Chemistry
  作者：Cecilia Saiz、Peter Wipf、Eduardo Manta、Graciela Mahler

  DOI：10.1021/ol901104a

  日期：2009.8.6

  were generated using the reversible aminothiol exchange reaction of thiazolidines and aromatic aldehydes. The reaction proceeded in aqueous buffered media at pH 4 and room temperature to generate thermodynamically controlled mixtures of heterocycles. The synthesis of an enantiomerically pure thiazolidinyloxazolidine is also reported. The oxazolidine moiety could be exchanged in CH2Cl2 in the presence

  使用噻唑烷和芳香醛的可逆氨基硫醇交换反应生成了新的动态组合库 (DCL)。该反应在 pH 4 和室温的水性缓冲介质中进行，以生成热力学控制的杂环混合物。还报道了对映体纯的噻唑烷基恶唑烷的合成。恶唑烷部分可以在催化p- TsOH存在下在 CH 2 Cl 2中交换。