2-bromo-2-methyloctane | 148808-73-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 2-bromo-2-methyloctane
• CAS: 148808-73-5
• 化学式: C₉H₁₉Br
• 分子量: 207.154
• InChiKey: SVNCGMMQZANBMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  59 °C(Press: 3 Torr)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  10
• 可旋转键数：
  5
• 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-bromo-2-methyloctane 在 lithium aluminium tetrahydride 、 silver perchlorate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到2-甲基辛烷
  参考文献：
  名称：

  SILVER-CATALYZED REDUCTIVE DEHALOGENATION OF 1,1-DIBROMOCYCLOPROPANES

  摘要：

  1,1-二溴环丙烷在四氢呋喃中以LiAlH4-1 mol%的银高氯酸盐处理，迅速还原为相应的单溴产物，产率很高，推测是通过银催化的自由基链机制进行反应的。

  DOI：

  10.1246/cl.1983.1877
• 作为产物：
  描述：

  2-甲基-2-辛醇 在 氢溴酸 、 lithium bromide 作用下， 以 乙醚 、 水 为溶剂， 以76%的产率得到2-bromo-2-methyloctane
  参考文献：
  名称：

  硅烷醇基表面活性剂：一类创新的环保型清洁剂的合成途径和性质

  摘要：

  在此，探索了基于新型硅烷醇作为等电子膦酸酯的替代物的环保型表面活性剂。水溶液的表面张力显着降低，尤其是那些有机部分与硅烷醇比例高的硅烷醇。除了用作表面活性剂外，还以玻璃基材为例研究了它们作为亲水性氧化物表面涂料的潜力。在含硅烷醇的固态片状结构中，存在双层，其中片状间距随烷基链长而变化。

  DOI：

  10.1002/chem.201402857

文献信息

• Titanocene-catalyzed alkylative dimerization of vinyl Grignard reagent using alkyl halides
  作者：Yuuki Fujii、Jun Terao、Yuichiro Kato、Nobuaki Kambe

  DOI：10.1039/b813596g

  日期：——

  Dimerization of vinyl Grignard reagents and concomitant alkylation with alkyl halides have been achieved by using Cp(2)TiCl(2) as a catalyst.

  乙烯基格氏试剂的二聚和伴随烷基卤化物的烷基化已通过使用Cp（2）TiCl（2）作为催化剂来实现。
• Nickel-Catalyzed anti-Markovnikov Hydroalkylation of Trifluoromethylalkenes
  作者：Chuan Zhu、Heng Zhang、Qian Liu、Kai Chen、Ze-Yao Liu、Chao Feng

  DOI：10.1021/acscatal.2c02052

  日期：2022.8.5

  employed because of facile β-fluoride elimination pathways. Herein, we report a hydroalkylation of trifluoromethylalkenes with alkyl halides under nickel catalysis that enables the rapid construction of 1,1,1-trifluoropropane derivatives. The common β-fluoride elimination pathway is suppressed by identifying a competent proton donor that favors a protonolysis process. Also, unactivated alkenes could be

  烯烃的过渡金属催化双官能化构成了一个肥沃的合成平台，可用于从大宗化学品中快速获取复杂分子。然而，由于易于 β-氟化物消除途径，很少使用具有氟烷基取代基的底物。在此，我们报道了在镍催化下三氟甲基烯烃与卤代烷的氢化烷基化反应，能够快速构建 1,1,1-三氟丙烷衍生物。通过识别有利于质子分解过程的合格质子供体来抑制常见的 β-氟化物消除途径。此外，当使用 Ni/氢化硅烷催化体系时，未活化的烯烃可以很容易地用作烷基供体。
• Nickel‐Catalyzed C−I‐Selective C(<i>sp</i>²)−C(<i>sp</i>³) Cross‐Electrophile Coupling of Bromo(iodo)arenes with Alkyl Bromides
  作者：Xiaoyuan Ying、Yuxi Li、Luyang Li、Chao Li

  DOI：10.1002/anie.202304177

  日期：2023.6.26

  bromo(iodo)arenes with 3°, 2°, and 1°alkyl bromides is reported. This mild XEC displays a broad scope with demonstrated functional group tolerance and finds use in the streamlined preparation of synthetically challenging bioactive compounds. Given the prevalence of its building blocks and the substrate generality, this discovery will likely inspire numerous applications.

  报道了溴（碘）芳烃与 3°、2° 和 1° 烷基溴化物的C( sp 2 )-I 选择性交叉亲电偶联 (XEC)的方法。这种温和的 XEC 显示出广泛的范围和已证明的官能团耐受性，并可用于简化合成具有挑战性的生物活性化合物的制备。鉴于其构建模块的普遍性和底物的普遍性，这一发现可能会激发大量应用。
• Structure–Odor Correlations in Homologous Series of Alkanethiols and Attempts To Predict Odor Thresholds by 3D-QSAR Studies
  作者：Johannes Polster、Peter Schieberle

  DOI：10.1021/jf506135c

  日期：2015.2.11

  Homologous series of alkane-1-thiols, alkane-2-thiols, alkane-3-thiols, 2-methylalkane-1-thiols, 2-methylalkane-3-thiols, 2-methylalkane-2-thiols, and alkane-1,?-dithiols were synthesized to study the influence of structural changes on odor qualities and odor thresholds. In particular, the odor thresholds were strongly influenced by steric effects: In all homologous series a minimum was observed for thiols with five to seven carbon atoms, whereas increasing the chain length led to an exponential increase in the odor threshold. Tertiary alkanethiols revealed clearly lower odor thresholds than found for primary or secondary thiols, whereas neither a second mercapto group in the molecule nor an additional methyl substitution lowered the threshold. To investigate the impact of the SH group, odor thresholds and odor qualities of thiols were compared to those of the corresponding alcohols and (methylthio)alkanes. Replacement of the SH group by an OH group as well as S-methylation of the thiols significantly increased the odor thresholds. By using comparative molecular field analysis, a 3D quantitative structureactivity relationship model was created, which was able to simulate the odor thresholds of alkanethiols in good agreement with the experimental results. NMR and mass spectrometric data for 46 sulfur-containing compounds are additionally supplied.
• The Reaction of Silver Nitrite with Secondary and Tertiary Alkyl Halides^1,2
  作者：Nathan Kornblum、Robert A. Smiley、Herbert E. Ungnade、Alan M. White、Bernard Taub、Stephen A. Herbert

  DOI：10.1021/ja01626a028

  日期：1955.11