1,2-bis(2-fluorobenzyl)diselane | 823178-70-7

• 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: 1,2-bis(2-fluorobenzyl)diselane
• 英文别名: Diselenide, bis[(2-fluorophenyl)methyl]；1-fluoro-2-[[(2-fluorophenyl)methyldiselanyl]methyl]benzene
• CAS: 823178-70-7
• 化学式: C₁₄H₁₂F₂Se₂
• 分子量: 376.166
• InChiKey: FXEDTACYRWUCAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 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：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis(2-fluorobenzyl)diselane 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-fluorophenyl)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：

  1-(2-氟苯基)-N,N-二甲基甲胺 在 selenium 、 caesium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 16.0h， 生成 1,2-bis(2-fluorobenzyl)diselane
  参考文献：
  名称：

  从元素硒和苄基季铵盐合成二苄基二硒化物

  摘要：

  c ^ 2 -对称dibenzylic diselenides：由S表示的合成方法（对映体富集的高度）dibenzylic diselenides Ñ描述的（对映体富集）季铵盐和元素硒2亲核取代。

  DOI：

  10.1002/ejoc.202101086

文献信息

• A fast and direct iodide-catalyzed oxidative 2-selenylation of tryptophan
  作者：Yu-Ting Gao、Shao-Dong Liu、Liang Cheng、Li Liu

  DOI：10.1039/d1cc00700a

  日期：——

  We have developed a novel methodology for the synthesis of valuable 2-selenylated tryptophans from diselenides under the catalysis of iodide.

  我们已经开发出一种新颖的方法，可以在碘化物的催化下，从二硒化物合成具有价值的2-硒基色氨酸。
• Synthesis of Dibenzylic Diselenides from Elemental Selenium and Benzylic Quaternary Ammonium Salts
  作者：Feng Chen、Fuhai Li、Qingle Zeng

  DOI：10.1002/ejoc.202101086

  日期：2021.11.8

  C2-symmetric dibenzylic diselenides: A synthetic method for (highly enantioenriched) dibenzylic diselenides by SN2 nucleophilic substitution of (enantioenriched) quaternary ammonium salts and elemental selenium is described.

  c ^ 2 -对称dibenzylic diselenides：由S表示的合成方法（对映体富集的高度）dibenzylic diselenides Ñ描述的（对映体富集）季铵盐和元素硒2亲核取代。
• Experimental and Theoretical Studies on the Nature of Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms
  作者：Michio Iwaoka、Takayuki Katsuda、Hiroto Komatsu、Shuji Tomoda

  DOI：10.1021/jo048436a

  日期：2005.1.1

  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.