3,6-D2-cyclohexene | 52182-21-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3,6-D2-cyclohexene
• 英文别名: 3,6-Dideuteriocyclohexen；3,6-dideuterio-cyclohexene；3,6-Dideuteriocyclohexene；3,6-dideuteriocyclohexene
• CAS: 52182-21-5
• 化学式: C₆H₁₀
• 分子量: 84.1295
• InChiKey: HGCIXCUEYOPUTN-NMQOAUCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  6
• 可旋转键数：
  0
• 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

• 作为产物：
  描述：

  1,3-环己二烯 在 乙酰溴 、 氘代甲醇-d 、 氰基硼氘化钠 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 0.5h， 生成 3,4-d2-cyclohexene 、 3,6-D2-cyclohexene
  参考文献：
  名称：

  Quantitative Analyses of Stereoisomeric 3,4-d₂-Cyclohexenes in the Presence of 3,6-d₂-Cyclohexenes

  摘要：

  The challenging analytical problem posed by mixtures of the four isomeric 3,4-d(2)-cyclohexenes and the three isomeric 3,6-d(2)-cyclohexenes has been solved through a novel one-dimensional NMR spectroscopic method dependent on recording C-13 resonances while broadband decoupling both proton and deuteron nuclei. Upfield deuterium perturbations of C-13 chemical shifts in chair conformationally locked cyclohexane derivatives readily secured from a mixture of the seven deuterium-labeled cyclohexenes allow quantitative analytical assessments of the four possible 3,4-d(2)-cyclohexenes in the mixture. This analytical capability is an essential prerequisite for uncovering the relative participations of the four possible stereochemical paths followed by the thermal structural isomerizations of vinylcyclobutane to cyclohexene. The unconventional NMR method validated in this work will likely prove invaluable in related stereochemical investigations.

  DOI：

  10.1021/jo900430w

文献信息

• Well-Defined Cobalt(I) Dihydrogen Catalyst: Experimental Evidence for a Co(I)/Co(III) Redox Process in Olefin Hydrogenation
  作者：Kenan Tokmic、Charles R. Markus、Lingyang Zhu、Alison R. Fout

  DOI：10.1021/jacs.6b07066

  日期：2016.9.14

  the addition of Cp2ZrHCl, evolves hydrogen gas and regenerates the Co(I)-(N2) complex. Furthermore, the catalytic olefin hydrogenation activity of the Co(I) species was studied by using multinuclear and parahydrogen (p-H2) induced polarization (PHIP) transfer NMR studies to elucidate catalytically relevant intermediates, as well as to establish the role of the Co(I)-(H2) in the Co(I)/Co(III) redox cycle

  由 Co(I)-(N2) 前驱体制备的二氢钴 Co(I)-(H2) 复合物的合成，该前驱体由单阴离子钳形双（卡宾）配体（Mes）CCC（（Mes）CCC = bis（甲基-苯并咪唑-2-亚基)苯基)，描述。该物种能够在室温下对烯烃进行 H2/D2 加扰和氢化。将 HCl 化学计量添加到 Co(I)-(N2) 中，干净地提供了 Co(III) 氢氯化物络合物，在加入 Cp2ZrHCl 后，会放出氢气并再生 Co(I)-(N2) 络合物。此外，通过使用多核和仲氢 (p-H2) 诱导极化 (PHIP) 转移核磁共振研究来研究 Co(I) 物种的催化烯烃加氢活性，以阐明催化相关的中间体，并确定 Co (I)-(H2) 在 Co(I)/Co(III) 氧化还原循环中。
• “Imprinting” Catalytically Active Pd Nanoparticles onto Ionic-Liquid-Modified Al₂O₃Supports
  作者：Leandro Luza、Aitor Gual、Dario Eberhardt、Sérgio R. Teixeira、Sandra S. X. Chiaro、Jairton Dupont

  DOI：10.1002/cctc.201300123

  日期：2013.8

  Going against tradition: Uniformly distributed Pd nanoparticles on imidazolium‐ionic‐liquid‐modified Al2O3 surfaces are prepared by a top down approach by using a new sputtering chamber. The hydrogenation of 1,3‐cyclohexadiene is used to probe the surface properties of these new Pd nanoparticles.

  违背传统：使用新的溅射室通过自顶向下的方法制备在咪唑鎓离子液体改性的Al 2 O 3表面上均匀分布的Pd纳米颗粒。1,3-环己二烯的氢化用于探测这些新的Pd纳米颗粒的表面性能。
• On the Stereochemical Characteristic of the Thermal Reactions of Vinylcyclobutane
  作者：John E. Baldwin、Alexey P. Kostikov

  DOI：10.1021/jo1000675

  日期：2010.5.7

  This Perspective outlines the stereochemical and mechanistic complexities inherent in the thermal reactions converting vinylcyclobutane to cyclohexene, butadiene, and ethylene. The structural isomerization and the fragmentation processes seem, at first sight, to be obvious and simple. When considered more carefully and investigated with the aid of deuterium-labeled stereochemically well-defined vinylcyclobutane

  该观点概述了将乙烯基环丁烷转化为环己烯，丁二烯和乙烯的热反应固有的立体化学和机理复杂性。乍一看，结构异构化和片段化过程似乎是明显且简单的。当更仔细地考虑和借助氘标记的立体化学定义明确的乙烯基环丁烷衍生物进行研究时，出现了由56个结构间转换和12个独立的动力学参数所跟踪的复杂动力学情况。通过实验确定立体变异的立体化学细节，并[1，d 2-标记的乙烯基环丁烷起始原料为16种结构的混合物。
• Quantitative Analyses of Stereoisomeric 3,4-<i>d</i>₂-Cyclohexenes in the Presence of 3,6-<i>d</i>₂-Cyclohexenes
  作者：John E. Baldwin、David J. Kiemle、Alexey P. Kostikov

  DOI：10.1021/jo900430w

  日期：2009.5.15

  The challenging analytical problem posed by mixtures of the four isomeric 3,4-d(2)-cyclohexenes and the three isomeric 3,6-d(2)-cyclohexenes has been solved through a novel one-dimensional NMR spectroscopic method dependent on recording C-13 resonances while broadband decoupling both proton and deuteron nuclei. Upfield deuterium perturbations of C-13 chemical shifts in chair conformationally locked cyclohexane derivatives readily secured from a mixture of the seven deuterium-labeled cyclohexenes allow quantitative analytical assessments of the four possible 3,4-d(2)-cyclohexenes in the mixture. This analytical capability is an essential prerequisite for uncovering the relative participations of the four possible stereochemical paths followed by the thermal structural isomerizations of vinylcyclobutane to cyclohexene. The unconventional NMR method validated in this work will likely prove invaluable in related stereochemical investigations.