bis(2-bromobenzyl) diselenide | 57239-60-8

• 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: bis(2-bromobenzyl) diselenide
• 英文别名: 1-Bromo-2-[[(2-bromophenyl)methyldiselanyl]methyl]benzene
• CAS: 57239-60-8
• 化学式: C₁₄H₁₂Br₂Se₂
• 分子量: 497.977
• InChiKey: IAPSJZHHEGBWPG-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  515.1±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  bis(2-bromobenzyl) diselenide 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以100%的产率得到(2-bromophenyl)methaneselenenyl bromide
  参考文献：
  名称：

  Experimental and Theoretical Studies on the Nature of Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms

  摘要：

  To investigate the nature of weak nonbonded selenium(...)halogen interactions ((SeX)-X-... interactions; X = F Cl, and Br), three types of model compounds [2-(CH2X)C6H4SeY (1-3), 3-(CH2X)-2-C10H6-SeY (4-6), and 2-XC6H4CH2SeY (7-9); Y = CN, Cl, Br, SeAr, and Me] were synthesized, and their Se-77 NMR spectroscopic behaviors were analyzed in CDCl3. The gradual upfield shifts of Se-77 NMR absorptions observed for series 1-3 and 4-6 suggested that the strength of (SeX)-X-... interaction decreases in the order of (SeF)-F-... > (SeCl)-Cl-... > (SeBr)-Br-.... The quantum chemical calculations at the B3LYP/631H level using the polarizable continuum model (PCM) revealed that the most stable conformer for 1-3 is the one with an intramolecular short (SeX)-X-... atomic contact in CHCl3 (epsilon = 4.9) and also that the n(x) --> sigma*(se-y) orbital interaction (E-Se...X) can reasonably explain the order of strength for the (SeX)-X-... interactions. On the other hand, the Se-77 NMR absorptions observed for series 7-9 did not shift significantly from the reference compounds (C6H5CH2SeY), indicating the absence of the (SeX)-X-... interaction for 7-9 presumably due to attenuation of basicity for the halogen atom that is substituted directly to the aromatic ring. These observations suggested that the n(x) --> sigma*(se-y) orbital interaction is a dominant factor for formation of weak (SeX)-X-... interactions. Electron correlation was also suggested to be important for the stability.

  DOI：

  10.1021/jo048436a
• 作为产物：
  描述：

  2-溴溴苄 在 sodium hydroxide 、 selenium 、 一氧化碳 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以73%的产率得到bis(2-bromobenzyl) diselenide
  参考文献：
  名称：

  常压下有机卤化物合成有机二硒化物的改进方法

  摘要：

  摘要 报道了一种合成有机二硒化物的改进方法。该方法包括有机卤化物与硒、一氧化碳和水在常压下在无机碱氢氧化钠存在下反应，以良好的收率得到有机二硒化物。

  DOI：

  10.1080/00397910701465404

文献信息

• Visible Light-Mediated C(sp²)–H Selenylation of Amino Pyrazole and Amino Uracils in the Presence of Rose Bengal as an Organophotocatalyst
  作者：Danish Ali、Tasneem Parvin、Lokman H. Choudhury

  DOI：10.1021/acs.joc.1c02565

  日期：2022.1.21

  arylselenoethers by a catalyst-free one-pot three-component reaction. The notable features of this methodology are metal-free reaction conditions, good to very good yields, use of an organic photocatalyst, and wide substrate scope; it is also applicable to gram-scale synthesis and provides selenoethers of medicinally important heterocycles such amio-pyrazole, isoxazole, isothiazole, and uracils.

  在此，我们报道了一种通过 C(sp 2 ) 合成氨基吡唑和氨基尿嘧啶的烷基、苄基和苯基硒醚的有效方法。)–H 官能化在可见光和玫瑰红作为有机光催化剂存在下。氨基吡唑/异噻唑/异恶唑或氨基尿嘧啶与 0.5 当量的二苯基/二苄基/二乙基二硒化物在可见光存在下，在乙腈介质和催化量的玫瑰红中反应，得到相应的苯基、苄基或乙基硒醚。到非常好的产量。我们还利用一些硒化氨基吡唑通过无催化剂的一锅三组分反应制备与芳基硒醚结合的吡唑稠合二氢嘧啶。该方法的显着特点是无金属反应条件、良好至非常好的产率、使用有机光催化剂和广泛的底物范围；
• Design, synthesis, and biological evaluation of novel miconazole analogues containing selenium as potent antifungal agents
  作者：Hang Xu、Xin Su、Meng-bi Guo、Ran An、Yan-hua Mou、Zhuang Hou、Chun Guo

  DOI：10.1016/j.ejmech.2020.112360

  日期：2020.7

  Herein, based on the theory of bioisosterism, a series of novel miconazole analogues containing selenium were designed, synthesized and their inhibitory effects on thirteen strains of pathogenic fungi were evaluated. It is especially encouraging that all the novel target compounds displayed significant antifungal activities against all tested strains. Furthermore, all the target compounds showed excellent

  在此，根据生物立体异构理论，设计，合成了一系列新型的含硒咪康唑类似物，并评价了它们对十三种致病真菌的抑制作用。特别令人鼓舞的是，所有新型目标化合物均对所有测试菌株均表现出显着的抗真菌活性。此外，所有目标化合物均对耐氟康唑的真菌表现出优异的抑制作用。随后，初步的机理研究表明，代表性化合物A03对C.alb具有很强的抑制作用。CYP51。而且，目标化合物可以防止真菌生物膜的形成。进一步的溶血试验证实，潜在化合物比咪康唑具有更高的安全性。此外，分子对接研究提供了目标化合物与C.alb之间的相互作用模式。CYP51。这些结果强烈表明，某些目标化合物有望成为新型抗真菌药物。
• Design, synthesis and antifungal activities of novel triazole derivatives with selenium-containing hydrophobic side chains
  作者：Meng-bi Guo、Zhong-zuo Yan、Xin Wang、Hang Xu、Chun Guo、Zhuang Hou、Ping Gong

  DOI：10.1016/j.bmcl.2022.129044

  日期：2022.12

  In this work, a series of novel 1,2,4-triazole derivatives with selenium-containing hydrophobic side chains were designed and synthesized based on the structure of lanosterol 14α-demethylase (CYP51). All compounds were characterized by HRMS, 1H NMR and 13C NMR. Then, their antifungal activities against eight human pathogenic fungi were evaluated in vitro by testing the minimal inhibitory concentrations

  本工作基于羊毛甾醇 14α-脱甲基酶 (CYP51) 的结构，设计并合成了一系列具有含硒疏水侧链的新型 1,2,4-三唑衍生物。所有化合物均通过 HRMS、1 H NMR和13 C NMR进行了表征。然后，在体外评估了它们对八种人类病原真菌的抗真菌活性通过测试最小抑菌浓度。结果表明，几乎所有测试的化合物被发现比对照药物氟康唑更有效地对抗所有测试的真菌菌株。进一步的机理研究表明，目标化合物具有真菌CYP51抑制活性。同时，代表性化合物显示出对哺乳动物细胞系的低细胞毒性作用。此外，对接结果表明，目标化合物与白色念珠菌CYP51 的结合模式优于氟康唑，尤其是在狭窄的疏水裂缝中。总的来说，可以进一步开发具有含硒疏水侧链的新型 1,2,4-三唑衍生物，用于治疗侵袭性真菌感染。
• Lead optimization generates selenium-containing miconazole CYP51 inhibitors with improved pharmacological profile for the treatment of fungal infections
  作者：Hang Xu、Zhong-zuo Yan、Meng-bi Guo、Ran An、Xin Wang、Rui Zhang、Yan-hua Mou、Zhuang Hou、Chun Guo

  DOI：10.1016/j.ejmech.2021.113337

  日期：2021.4
• Wang, Jin-Xian; Cui, Wenfeng; Hu, Yulai, Journal of the Chemical Society. Perkin transactions I, 1994, # 16, p. 2341 - 2344
  作者：Wang, Jin-Xian、Cui, Wenfeng、Hu, Yulai

  DOI：——

  日期：——