2-Thioxo-imidazolidine-1,3-dicarboxylic acid dibenzyl ester | 173300-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Thioxo-imidazolidine-1,3-dicarboxylic acid dibenzyl ester
• 英文别名: Dibenzyl 2-sulfanylideneimidazolidine-1,3-dicarboxylate
• CAS: 173300-82-8
• 化学式: C₁₉H₁₈N₂O₄S
• 分子量: 370.429
• InChiKey: GEIYMSJSRMJBOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  91.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Thioxo-imidazolidine-1,3-dicarboxylic acid dibenzyl ester 在 四氢吡咯 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 生成 1-Cbz-吡咯烷 、 Benzyl 2-sulfanylideneimidazolidine-1-carboxylate
  参考文献：
  名称：

  Alkoxycarbonyl groups transfer to amines by the N,N′-dibenzyl-and N,N′-di-tert-butyl-carbamates of cyclic thioureas

  摘要：

  The use of the dicarbamates of cyclic thioureas as alkoxycarbonyl-transfer reagents for the protection of amino groups is described.

  DOI：

  10.1039/p19950002953
• 作为产物：
  描述：

  亚乙基硫脲 、 氯甲酸苄酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以60%的产率得到2-Thioxo-imidazolidine-1,3-dicarboxylic acid dibenzyl ester
  参考文献：
  名称：

  Photochemical Properties of Red-Emitting Tris(cyclometalated) Iridium(III) Complexes Having Basic and Nitro Groups and Application to pH Sensing and Photoinduced Cell Death

  摘要：

  Cyclometalated iridium(III) complexes, because of their photophysical properties, have the potential for use as luminescent probes for cellular imaging. We previously reported on a pH-activatable iridium complex that contains three N,N-diethylamino groups, namely, fac-Ir(deatpy)(3) 5, which was synthesized via a regioselective aromatic substitution reaction at the 5'-position with tolylpyridine groups of fac-Ir(tpy)(3) 2. It was found that 5 shows a considerable enhancement in emission intensity in the pH range from neutral to slightly acidic (pH 6.5-7.4) in aqueous solution and selectively stains lysosome in HeLa-S3 cells, due to the protonation of the diethylamino groups. In addition, 5 functions as a pH-dependent singlet oxygen (O-1(2)) generator and induces necrosis-like cell death. However, observing the green emission of 5 is often hampered by autofluorescence emanating from nearby tissues. To overcome this problem, we designed and synthesized a series of new pH-activatable Ir(III) complexes that contain diethylamino, guanidyl, and iminoimidazolidinyl groups on the mpiq ligand of Ir(mpiq)(3) 7 and the tfpiq ligand of Ir(tfpiq)3 8, which exhibit a red emission, namely, Ir(deampiq)(3) 13, Ir(gmpiq)(3) 14, Ir(imzmpiq)(3) 15, and Ir(imztfpiq)(3) 16. The emission intensity of these Ir complexes is enhanced substantially by protonation of their basic groups, and they induce the necrosis-like cell death of HeLa-S3 cells by photoirradiation at 465 nm. A strong orange-red emission of Ir(mpiq-NO2)(3) 9 and Ir(tfpiq-NO2)(3) 10 is also reported.

  DOI：

  10.1021/acs.inorgchem.5b00369

文献信息

• Photochemical Properties of Red-Emitting Tris(cyclometalated) Iridium(III) Complexes Having Basic and Nitro Groups and Application to pH Sensing and Photoinduced Cell Death
  作者：Aya Kando、Yosuke Hisamatsu、Hiroki Ohwada、Taiki Itoh、Shinsuke Moromizato、Masahiro Kohno、Shin Aoki

  DOI：10.1021/acs.inorgchem.5b00369

  日期：2015.6.1

  Cyclometalated iridium(III) complexes, because of their photophysical properties, have the potential for use as luminescent probes for cellular imaging. We previously reported on a pH-activatable iridium complex that contains three N,N-diethylamino groups, namely, fac-Ir(deatpy)(3) 5, which was synthesized via a regioselective aromatic substitution reaction at the 5'-position with tolylpyridine groups of fac-Ir(tpy)(3) 2. It was found that 5 shows a considerable enhancement in emission intensity in the pH range from neutral to slightly acidic (pH 6.5-7.4) in aqueous solution and selectively stains lysosome in HeLa-S3 cells, due to the protonation of the diethylamino groups. In addition, 5 functions as a pH-dependent singlet oxygen (O-1(2)) generator and induces necrosis-like cell death. However, observing the green emission of 5 is often hampered by autofluorescence emanating from nearby tissues. To overcome this problem, we designed and synthesized a series of new pH-activatable Ir(III) complexes that contain diethylamino, guanidyl, and iminoimidazolidinyl groups on the mpiq ligand of Ir(mpiq)(3) 7 and the tfpiq ligand of Ir(tfpiq)3 8, which exhibit a red emission, namely, Ir(deampiq)(3) 13, Ir(gmpiq)(3) 14, Ir(imzmpiq)(3) 15, and Ir(imztfpiq)(3) 16. The emission intensity of these Ir complexes is enhanced substantially by protonation of their basic groups, and they induce the necrosis-like cell death of HeLa-S3 cells by photoirradiation at 465 nm. A strong orange-red emission of Ir(mpiq-NO2)(3) 9 and Ir(tfpiq-NO2)(3) 10 is also reported.
• Alkoxycarbonyl groups transfer to amines by the N,N′-dibenzyl-and N,N′-di-tert-butyl-carbamates of cyclic thioureas
  作者：Noboru Matsumura、Akiko Noguchi、Aya Kitayoshi、Hiroo Inoue

  DOI：10.1039/p19950002953

  日期：——

  The use of the dicarbamates of cyclic thioureas as alkoxycarbonyl-transfer reagents for the protection of amino groups is described.