2,4-二甲基己-2-烯 | 14255-23-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 2,4-二甲基己-2-烯
• 英文名称: 2,4-dimethylhex-2-ene
• 英文别名: 2,4-Dimethyl-hex-2-en；2,4-Dimethyl-2-hexene
• CAS: 14255-23-3
• 化学式: C₈H₁₆
• 分子量: 112.215
• InChiKey: IZSBIPQYBGDXJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  4-苯基-1,2,4-三唑啉-3,5-二酮 、 2,4-二甲基己-2-烯 以 氯仿 为溶剂， 生成 1-(1-Isopropenyl-2-methyl-butyl)-4-phenyl-[1,2,4]triazolidine-3,5-dione
  参考文献：
  名称：

  三唑啉二酮与手性烯丙基醇的非对映选择性烯反应。亲羟基分子转向作用的证据

  摘要：

  PTAD与手性烯丙醇4-甲基-3-戊烯-2-醇的烯反应在非极性溶剂中表现出高的苏非对映选择性，而在极性溶剂中，非对映选择性显着降低。根据非对映异构体顺式和反叠氮基亚胺中间体的形成过程中羟基与传入的亲油体之间的导向作用来讨论这些结果。

  DOI：

  10.1016/s0040-4039(98)00207-x
• 作为产物：
  描述：

  2,4-二甲基-3-己酮 在 aluminum oxide 、 copper oxide-chromium oxide 作用下， 175.0~350.0 ℃ 、12.26 MPa 条件下， 生成 2,4-二甲基己-2-烯
  参考文献：
  名称：

  The Reaction of Mesityl Oxide with t-Butylmagnesium Chloride

  摘要：

  DOI：

  10.1021/ja01157a016

文献信息

• Stereochemistry in the Ene Reactions of Singlet Oxygen and Triazolinediones with Allylic Alcohols. A Mechanistic Comparison
  作者：Georgios Vassilikogiannakis、Manolis Stratakis、Michael Orfanopoulos、Christopher S. Foote

  DOI：10.1021/jo990258b

  日期：1999.5.1

  The ene reaction of singlet oxygen with (Z)-4-methylpent-3-en-2-ol-2,5,5,5-d(4) (1-OH-d4) in nonpolar solvents exhibits a 90% three diastereoselectivity in the adduct derived from the major syn perepoxide intermediate, but also a moderate three diastereoselectivity in the adduct derived from the minor anti perepoxide. Photooxygenation of 2,4-dimethylpent-3-en-2-ol (2) exhibits a significant solvent dependence in the syn/anti methyl stereoselectivity, with nonpolar solvents promoting syn methyl reactivity, while polar solvents promote anti methyl reactivity. These results are in agreement with a steering effect between hydroxyl and singlet oxygen in the rate-determining step of the reaction. N-Phenyltriazolinedione addition to the chiral allylic alcohol 4-methylpent-3-en-2-ol (1-OH) is highly three diastereoselective in nonpolar solvents, with a solvent dependent variation in the threo/erythro ene products. On the other hand, the nonfunctionalized chiral alkene 2,4-dimethyl-2-hexene (1-Et) exhibits poor diastereoselectivity. Reaction of PTAD with 1-OH-d4 in nonpolar solvents, exhibits a significant three diastereoselectivity from the syn aziridinium imide intermediate, and a moderate three diastereoselectivity from the anti intermediate. These results are consonant with a steering effect between the hydroxyl and the electrophile, as proposed in the case of singlet oxygen addition to allylic alcohols 1-OH and 2. In contrast to the analogous O-1(2) ene reaction, a solvent independent ratio syn/anti similar to 50/50 was found in the addition of MTAD to 2. The intermolecular kinetic isotope effect in the reaction of 2 with MTAD (k(H)/k(D) = 1.15 +/- 0.02), is consistent with formation of the intermediate in fast step, indicative that the steering effect during the formation of aziridium imide is not important in the reaction kinetics. This energetic profile is in contrast to triazolinedione addition to the secondary allylic alcohol 1-OH, where the high three selectivity and the slight inverse kinetic isotope effect of k(H)/k(D) = 0.98 +/- 0.02 are consonant with the formation of the intermediate in the rate-determining step. An explanation for the increased reactivity of the syn methyl in the addition of MTAD to 2 (similar to 50%) is offered.
• New triad alkylation reagent. Cross coupling of indium trialkyls with alkenyl halides
  作者：Ryoki Nomura、Shinichiro Miyazaki、Haruo Matsuda

  DOI：10.1021/ja00033a070

  日期：1992.3
• The Reaction of Mesityl Oxide with t-Butylmagnesium Chloride
  作者：Frank C. Whitmore、D. P. J. Goldsmith、N. C. Cook、J. C. Yarze、G. G. Ecke

  DOI：10.1021/ja01157a016

  日期：1950.1
• Diastereoselective ene reactions of triazolinediones with chiral allylic alcohols. Evidence for a hydroxyl-enophile steering effect
  作者：Manolis Stratakis、Georgios Vassilikogiannakis、Michael Orfanopoulos

  DOI：10.1016/s0040-4039(98)00207-x

  日期：1998.4

  The ene reaction of PTAD with the chiral allylic alcohol 4-methyl-3-penten-2-ol exhibits high threo diastereoselectivity in non polar solvents, whereas in polar solvents the diastereoselectivity decreases substantially. These results are discussed in terms of a steering effect between the hydroxyl and the incoming enophile during the formation of the diastereomeric syn and anti aziridinium imide intermediates

  PTAD与手性烯丙醇4-甲基-3-戊烯-2-醇的烯反应在非极性溶剂中表现出高的苏非对映选择性，而在极性溶剂中，非对映选择性显着降低。根据非对映异构体顺式和反叠氮基亚胺中间体的形成过程中羟基与传入的亲油体之间的导向作用来讨论这些结果。

表征谱图