2,2-二溴-3,3-二甲基丁烷 | 594-77-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 中文名称: 2,2-二溴-3,3-二甲基丁烷
• 英文名称: 2,2-Dibrom-3,3-dimethyl-butan
• 英文别名: 2,2-Dibromo-3,3-dimethylbutane
• CAS: 594-77-4
• 化学式: C₆H₁₂Br₂
• 分子量: 243.969
• InChiKey: SAJVFWRGLXVNOL-UHFFFAOYSA-N

物化性质

• 沸点：
  172.9±8.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2,2-二溴-3,3-二甲基丁烷 、 alkaline earth salt of/the/ methylsulfuric acid 生成 3,3-二甲基-1-丁炔
  参考文献：
  名称：

  Faworski; Welitschkowskaja, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1912, vol. 44, p. 1371

  摘要：

  DOI：
• 作为产物：
  描述：

  频哪酮 在 五溴化磷 作用下， 生成 2,2-二溴-3,3-二甲基丁烷
  参考文献：
  名称：

  Delacre, Chemisches Zentralblatt, 1906, vol. 77, # II, p. 497

  摘要：

  DOI：

文献信息

• Alkenyl Bromides by Brominative Deoxygenation of Ketones in One or Two Steps
  作者：Ulrich Von Roman、Jakob Ruhdorfer、Rudolf Knorr

  DOI：10.1055/s-1993-25986

  日期：——

  The conversion of ketones into alkenyl bromides is accomplished in one or two steps by 2,2,2-tribromo-2,2-dihydro-1,3,2-benzodioxaphosphole or by the dibromomethyl methyl ether prepared therefrom. Investigations of the scope and limitations provide some hints for the preparative planning and improvement.

  通过使用2,2,2-三溴-2,2-二氢-1,3,2-苯并二氧磷杂环己烯或由此制备的二溴甲基甲醚，可以将酮转化为烯基溴，这一过程在一到两步内完成。对范畴和限制条件的研究为制备规划和改进提供了一些线索。
• Nuclear magnetic resonance spectroscopy. Barriers to internal rotation in some halogenated methylbutanes
  作者：John D. Roberts、Bruce L. Hawkins、Wolfgang Bremser、S. Borcic

  DOI：10.1021/ja00747a022

  日期：1971.9

  Barriers to internal rotation about the C(2)-C(3) bonds have been determined for ten closely related halogenated methylbutanes by detailed line-shape analysis of their nuclear magnetic resonance spectra. The experimental barriers range from 9 to 16 kcal/mol. In addition, for some of the compounds investigated, free energy differences were obtained for rotational isomers under conditions of slow conformational

  十种密切相关的卤代甲基丁烷通过对其核磁共振谱的详细线形分析确定了 C(2)-C(3) 键内部旋转的障碍。实验屏障范围为 9 至 16 kcal/mol。此外，对于一些研究的化合物，在缓慢的构象交换条件下获得了旋转异构体的自由能差异。结果根据可能的非键相互作用进行讨论。
• Couturier, Annales de Chimie (Cachan, France), 1892, vol. <6>26, p. 450
  作者：Couturier

  DOI：——

  日期：——
• Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes
  作者：Paul J. Kropp、Scott D. Crawford

  DOI：10.1021/jo00090a031

  日期：1994.6

  The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes. The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ. Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH2Cl2 solution saturated with HCl, readily afforded the syn addition product, alkenyl chloride (E)-4a. On extended treatment (E)-4a underwent subsequent isomerization to the thermodynamically more stable Z isomer. Thus either isomer of 4a could be obtained in good yield depending on the reaction conditions. In a similar way bromides (E)- and (Z)-4b were obtained without competing formation of the radical products (E)- and (Z)-5, which occurred in solution. In contrast with solution-phase hydriodination of alkyne 1, which slowly afforded iodide (E)-4c, surface-mediated addition readily afforded (E)-4c, followed by isomerization to the Z isomer. E reversible arrow Z equilibration of the alkenyl halides 4 was shown to involve, at least in part, addition-elimination via the gem-dihalides 13. Analogous behavior was exhibited by the phenylalkynes 2 and 3 on surface-mediated hydrohalogenation. Surface-mediated addition of Hbr and HI to the internal alkylalkyne 14 afforded principally the anti addition products (Z)-15b,c. Treatment of the terminal alkynes 17 and 22 with (COBr)(2) over alumina gave the dibromides 20 and 24/25,respectively, whereas use of acetyl bromide as the Hbr precursor afforded the alkenyl bromides 18b and 23.
• Pross,A.; Sternhell,S., Australian Journal of Chemistry, 1971, vol. 24, p. 1437 - 1447
  作者：Pross,A.、Sternhell,S.

  DOI：——

  日期：——