diselenodipropionic acid dimethyl ester | 136397-82-5

• 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: diselenodipropionic acid dimethyl ester
• 英文别名: MeSeP；4,5-diselena-octanedioic acid dimethyl ester；4,5-Diselena-octandisaeure-dimethylester；Bis-(2-methoxycarbonyl-aethyl)-diselenid；methyl 3-[(3-methoxy-3-oxopropyl)diselanyl]propanoate
• CAS: 136397-82-5
• 化学式: C₈H₁₄O₄Se₂
• 分子量: 332.117
• InChiKey: CHXJIXPXFBCBMA-UHFFFAOYSA-N

物化性质

• 沸点：
  367.8±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  14.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diselenodipropionic acid dimethyl ester 在 谷胱甘肽 、 水 、 还原型辅酶II(NADPH)四钠盐 、 glutathione reductase 作用下， 生成
  参考文献：
  名称：

  Correlating the GPx Activity of Selenocystine Derivatives with One-Electron Redox Reactions

  摘要：

  With an aim to develop water soluble, less toxic glutathione peroxidase (GPx) mimics, three selenocystine (SeCys) derivatives, viz., selenocystamine (SeA), diselenodipropionic acid (SeP), and methyl ester of diselenodipropionic acid (MeSeP) have been synthesized and examined for GPx activity along with SeCys. The GPx activity of the compounds was found to be in the order SeCys congruent to SeA > MeSeP > SeP. The relative affinity of these GPx mimics towards the substrates thiol and hydroperoxide were determined by Lineweaver-Burk (L-B) plots. Since the enzyme activity involves several steps of reduction and oxidation reactions, attempts have been made to understand the role of such processes in deciding the efficacy of diselenides as GPx mimics. For this, one-electron redox chemistry of these compounds was studied in aqueous solutions at pH 7 using nanosecond pulse radiolysis technique. From these studies, it was concluded that SeCys and SeA, which can undergo easy one-electron reduction, exhibit high GPx activity.

  DOI：

  10.1080/10426500801901046
• 作为产物：
  描述：

  3-溴丙酸甲酯 在 disodium diselenide 作用下， 以52%的产率得到diselenodipropionic acid dimethyl ester
  参考文献：
  名称：

  二硒化物和烯丙基硒化物作为谷胱甘肽过氧化物酶模拟物。烯丙基ω-羟基烷基硒化物氧化原位生成环状硒酸盐的显着活性

  摘要：

  在模型系统中测试了一系列含有配位取代基的脂肪族二硒化物和硒化物的谷胱甘肽过氧化物酶（GPx）样催化活性，其中用苄硫醇还原叔丁基氢过氧化物以提供二苄基二硫化物和叔丁醇在下进行标准条件并通过 HPLC 监测。尽管二硒化物通常表现出较差的催化活性，但烯丙基硒化物证明更有效。特别是，烯丙基 3-羟丙基硒化物 (25) 通过一系列氧化和 [2,3] sigmatropic 重排步骤在原位快速生成 1,2-oxaselenolane Se-氧化物 (31)。显着活性的环状硒酸盐 31 被证明是真正的催化剂，通过假设的机制与硫醇反应，其中首先产生硫硒酸盐 32，

  DOI：

  10.1021/ja0357588

文献信息

• β-Functionalized ethylchalcogenolate complexes of lead(II): Synthesis, structures and their conversion into lead chalcogenide nanoparticles
  作者：Gotluru Kedarnath、Liladhar B. Kumbhare、Sandip Dey、Amey P. Wadawale、Vimal K. Jain、Goutam K. Dey

  DOI：10.1016/j.poly.2009.05.054

  日期：2009.9

  reactions of Pb(OAc) 2 ·3H 2 O with NaER yield homoleptic colorless to yellow complexes of composition, [Pb(ER) 2 ] (ER = SCH 2 CH 2 NMe 2 ( 1 ), SeCH 2 CH 2 NMe 2 ( 2 ) and SeCH 2 CH 2 COOMe ( 3 )). These complexes were characterized by elemental analyses, UV–Vis and 1 H NMR data. Molecular structures of [Pb(ECH 2 CH 2 NMe 2 ) 2 ] (E = S or Se) have been established by single crystal X-ray diffraction

  摘要Pb（OAc）2·3H 2 O与NaER的反应生成纯净的无色至黄色组合物[Pb（ER）2]（ER = SCH 2 CH 2 NMe 2（1），SECH 2 CH 2 NMe 2 （2）和SECH 2 CH 2 COOMe（3））。这些配合物的特征在于元素分析，UV-Vis和1 H NMR数据。通过单晶X射线衍射分析已经建立了[Pb（ECH 2 CH 2 NMe 2）2]的分子结构（E = S或Se）。这些分子在铅周围具有扭曲的三角双锥体构型，螯合硫属元素化物配体的氮原子占据轴向位置。通过TG分析研究了这些配合物的热行为。在炉中或在HDA（十六烷基胺）中进行热解，得到PbE纳米颗粒，其特征在于UV-Vis，光致发光，XRD，EDAX和TEM测量。
• Palladium(II) and platinum(II) 2-(methoxycarbonyl)ethylselenolates: Synthesis, spectroscopy, structures and their conversion into metal selenide
  作者：Liladhar B. Kumbhare、Vimal K. Jain、Prasad P. Phadnis、Munirathinam Nethaji

  DOI：10.1016/j.jorganchem.2006.12.003

  日期：2007.3

  was isolated from a reaction between Na2PdCl4 and MeOOCCH2CH2SeNa. All these complexes have been characterized by elemental analysis, IR, UV–Vis and NMR (1H, 13C, 31P, 77Se, 195Pt) spectroscopy. Structures of trans-[Pd2Cl2(μ-SeCH2CH2COOMe)2(PPh3)2] (2d), [Pt2Cl2(μ-Cl)(μ-SeCH2CH2COOMe)(PnPr3)2] (3e), [Pd3Cl2(μ-SeCH2CH2COOMe)4(PnPr3)2] (5) and [Pd(SeCH2CH2COOMe)2]6 (6) have been established unambiguously

  通过在甲醇中酯化（HOOCCH 2 CH 2 Se）2制备了二硒化物（MeOOCCH 2 CH 2 Se）2（1）。NaBH 4在甲醇中对Se-Se键在1中的还原性裂解生成MeOOCCH 2 CH 2 SeNa。在与[M不同的化学计量反应的后者2氯2（μ-Cl）的2（PR 3）2 ]，得到了各种组合物的产品[M 2氯2（μ-SECH 2 CH 2COOMe）2（PR 3）2 ]（2）；[M 2氯2（μ-Cl）的（μ-SECH 2 CH 2 COOMe）（PR 3）2 ]（3）; [钯2（SECH 2 CH 2 COOMe）2（μ-SECH 2 CH 2 COOMe）2（PR 3）2 ]（4）; [钯3氯2（μ-SECH 2 CH 2 COOMe）4（PR 3）2 ]（5）。复合物的治疗2与[M 2氯2（μ-Cl）的2（PR 3）2 ]，得到的复合物3中几乎定量的产率。这些反应中各种产物的形
• Oligomeric allyl-palladium(ii) complexes of β-substituted ethylselenolates: Syntheses, structures and thermal decomposition
  作者：Liladhar B. Kumbhare、Amey Wadawale、Sanjio S. Zade、Vimal K. Jain

  DOI：10.1039/c1dt10392j

  日期：——

  Tri-nuclear allyl-palladium complexes, [Pd(μ-SeCH2CH2COOR)(η3-C3H4R′)]3 (R = H, Me, Et and R′ = H, Me), have been synthesized by the reaction of [Pd2(μ-Cl)2(η3-C3H4R′)2] with NaSeCH2CH2COOR. These complexes exist in a dynamic equilibrium with a dimeric form in solution and are fluxional at room temperature as shown by variable temperature 1H NMR spectroscopy. The DFT calculations indicate that there is a negligible energy difference between the dimer and the trimer, and suggest that the delicate balance between the steric factors and angular strain decides the reaction products. These complexes (with R′ = H) on treatment with [Pd2(μ-Cl)2(η3-C3H5)2] afforded hetero-bridged complexes [Pd2(μ-Cl)(μ-SeCH2CH2COOR)(η3-C3H5)2] (R = Me, Et). All the complexes have been characterized by NMR (1H, 13C, 77Se) spectroscopy. The molecular structure of [Pd(μ-SeCH2CH2COOEt)(η3-C3H5)]3 revealed a chair conformation of the six-membered Pd3Se3 ring, in which all the allyl groups lie at one side of the ring (similar to three axial 1,3,5-hydrogens of cyclohexane). Thermolysis of [Pd(μ-SeCH2CH2COOEt)(η3-C3H5)]n in diphenyl ether or hexadecylamine (HDA) yielded Pd7Se4 as characterized by powder XRD.

  三核烯丙基钯配合物[Pd(µ-SeCH2CH2COOR)(·3-C3H4R²)]3（R = H、Me、Et，R² = H、Me）是通过[Pd2(µ-Cl)2(·3-C3H4R²)2]与NaSeCH2CH2COOR反应合成的。这些配合物在溶液中以二聚体形式存在，处于动态平衡状态，并且在室温下具有流动性，如可变温度1H NMR光谱所示。DFT计算表明，二聚体和三聚体之间的能量差异可以忽略不计，并且表明空间因素和角应变之间的微妙平衡决定了反应产物。这些配合物（R² = H）与[Pd2(µ-Cl)2(·3-C3H5)2]反应后，形成异桥联配合物[Pd2(µ-Cl)(µ-SeCH2CH2COOR)(·3- )2]（R = Me、Et）。所有配合物均通过NMR（1H、13C、77Se）光谱进行了表征。[Pd(µ-SeCH2CH2COOEt)(·3- )]3的分子结构显示，六元Pd3Se3环呈椅子构象，其中所有烯丙基基团位于环的一
• Preparation of beta,beta'-diselenodipropionic acid
  申请人：MACPEEK DONALD L

  公开号：US02729676A1

  公开（公告）日：1956-01-03