2,4-dibromo-2-dibromomethyl-1-selena-4-silacyclopent-4-ene | 676346-13-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2,4-dibromo-2-dibromomethyl-1-selena-4-silacyclopent-4-ene
• 英文别名: 2,4-dibromo-2-dibromomethyl-3,3-dimethyl-1-selena-3-sila-4-cyclopentene；2,4-dibromo-2-dibromomethyl-3,3-dimethyl-1-selena-3-sylacyclopentene-4；2,4-dibromo-2-(dibromomethyl)-3,3-dimethyl-1,3-selenasilole
• CAS: 676346-13-7
• 化学式: C₆H₈Br₄SeSi
• 分子量: 506.791
• InChiKey: CJIRBTZUPBPQML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2,4-dibromo-2-dibromomethyl-1-selena-4-silacyclopent-4-ene 生成 3,5-Dibromo-4,4-dimethyl-4H-[1,4]selenasiline 、 2,3,5-Tribromo-4,4-dimethyl-4H-[1,4]selenasiline
  参考文献：
  名称：

  Mass spectra of 3,6-dihalo-4,4-dimethyl-1,4-selenasilafulvenes and 2,4-dihalo-2-dihalomethyl-3,3-dimethyl-1-selena-3-silacyclopent-4-enes

  摘要：

  在电子电离和热分解条件下研究了新的杂环系统（即3,6-二卤-4,4-二甲基-1,4-硒-硅杂环戊烯1a、b和2,4-二卤-2-二卤甲基-3,3-二甲基-1-硒-3-硅杂环戊烯2a、b（卤=氯、溴））的行为。它们的断裂伴随着骨架重排，正电荷主要位于含硅的离子上。硒硅杂环戊烯1a、b形成稳定的分子离子。硒硅杂环戊烯2a部分分解，化合物2b在气相中完全分解，同时消除一个卤化氢和一个卤素分子。

  DOI：

  10.1007/s11172-005-0300-x
• 作为产物：
  描述：

  二乙炔基(二甲基)硅烷 在 溴化硒(IV) 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以60%的产率得到2,4-dibromo-2-dibromomethyl-1-selena-4-silacyclopent-4-ene
  参考文献：
  名称：

  四溴化硒与二甲基二乙炔基硅烷的反应

  摘要：

  DOI：

  10.1023/a:1024794103851

文献信息

• Mechanism of the cyclization of dimethyl diethynyl silane with selenium tetrabromide: Computational and structural studies, and monitoring
  作者：Svetlana V. Amosova、Vladimir A. Shagun、Alexander V. Martynov、Natalia A. Makhaeva、Lyudmila I. Larina、Konstantin A. Lysenko、Mikhail G. Voronkov

  DOI：10.1016/j.jorganchem.2007.01.023

  日期：2007.7

  The structure of 2,4-dibromo-2-dibromomethyl-3,3-dintethyl-1-selena-3-silacyclopentene-4, formed by regioselective electrophilic addition of SeBr4 to dimethyl diethynyl silane, has been determined using X-ray analysis technique. Quantum chemistry methods were used to study elementary stages of the reaction. It was found that the first stage consisted of SeBr4 conversion into bimolecular complex Br-2... SeBr2, initiated by dimethyl diethynyl silane. Possible formation of five-membered and six-membered heterocycles involves different cyclization mechanisms. The formation of only five-membered heterocycle is explained by kinetically preferable ring closure through four-center transition state. The conclusions obtained by calculations were confirmed by monitoring of the reaction using H-1 NMR method. (c) 2007 Elsevier B.V. All rights reserved.
• ——
  作者：V. A. Potapov、S. V. Amosova、O. V. Belozerova、A. I. Albanov、O. G. Yarosh、M. G. Voronkov

  DOI：10.1023/a:1024794103851

  日期：——
• Mass spectra of 3,6-dihalo-4,4-dimethyl-1,4-selenasilafulvenes and 2,4-dihalo-2-dihalomethyl-3,3-dimethyl-1-selena-3-silacyclopent-4-enes
  作者：L. V. Klyba、S. V. Amosova、O. V. Belozerova、V. A. Potapov、E. R. Zhanchipova、O. G. Yarosh、M. G. Voronkov

  DOI：10.1007/s11172-005-0300-x

  日期：2005.3

  The behavior of new heterocyclic systems, viz., 3,6-dihalo-4,4-dimethyl-1,4-selena- silafulvenes 1a, b and 2,4-dihalo-2-dihalomethyl-3,3-dimethyl-1-selena-3-silacyclopent-4-enes 2a, b (Hal =Cl, Br), was studied under conditions of electron ionization and thermal decomposition. Their fragmentation is accompanied by skeletal rearrangements, and the positive charge is localized mainly on ions containing silicon. Selenasilafulvenes 1a, b form stable molecular ions. Selenasilacyclopent-4-ene 2a decomposes partially and compound 2b decomposes completely in the gas phase with the elimination of a hydrogen halide and a halogen molecules.

  在电子电离和热分解条件下研究了新的杂环系统（即3,6-二卤-4,4-二甲基-1,4-硒-硅杂环戊烯1a、b和2,4-二卤-2-二卤甲基-3,3-二甲基-1-硒-3-硅杂环戊烯2a、b（卤=氯、溴））的行为。它们的断裂伴随着骨架重排，正电荷主要位于含硅的离子上。硒硅杂环戊烯1a、b形成稳定的分子离子。硒硅杂环戊烯2a部分分解，化合物2b在气相中完全分解，同时消除一个卤化氢和一个卤素分子。