1,exo-3-Dimethylbicyclo<2.2.1>heptan-2-on | 28644-57-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,exo-3-Dimethylbicyclo<2.2.1>heptan-2-on
• 英文别名: (1R,3R,4S)-1,3-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 28644-57-7；28767-95-5；80538-37-0
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: XSBBRSJXZUUBDR-BKPPORCPSA-N

物化性质

• 沸点：
  196.3±8.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,exo-3-Dimethylbicyclo<2.2.1>heptan-2-on 生成 (+/-)-1.3exo-dimethyl-norbornanone-(2)-semicarbazone
  参考文献：
  名称：

  Laukola zit. bei Pulkkinen, Annales Academiae Scientiarum Fennicae, Series A2: Chemica, 1956, # 74, p. 51

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 1,exo-3-Dimethylbicyclo<2.2.1>heptan-2-on
  参考文献：
  名称：

  Laukola zit. bei Pulkkinen, Annales Academiae Scientiarum Fennicae, Series A2: Chemica, 1956, # 74, p. 51

  摘要：

  DOI：

文献信息

• Reaction Sequences Involving the Mutual Interconversion of All 10 Tertiary Dimethyl-2-norbornyl Cations. A Comparison of Predicted Products and Rates with Experiment
  作者：R. Haseltine、K. Ranganayakulu、N. Wong、T. S. Sorensen

  DOI：10.1139/v75-265

  日期：1975.7.1

  All 10 tertiary dimethyl-2-norbornyl cations have been prepared. There are sequences of individual steps which will in theory interconvert any given two of these cations, a total of 45 permutations. All of the possible sequences (within a defined limit on the allowable total number of steps) for performing these interconversions were determined using a digital computer. Each step used in the computer generated sequence had previously been assigned a trial activation free energy value and a comparison is made in this paper between the actual experimental rearrangement results (in terms of both the kinetics of disappearance for the cation and what product is in fact formed) and the predicted results.

  已制备了所有10种三级二甲基-2-去氢-去甲基环辛基阳离子。存在一系列单独步骤的序列，理论上可以相互转化这些阳离子中的任意两种，共45种排列组合。使用数字计算机确定了执行这些相互转化的所有可能序列（在允许的总步数限制内）。计算机生成的序列中使用的每个步骤都先前被分配了一个试验性活化自由能值，在本文中对实际实验重排结果（包括阳离子消失的动力学和实际形成的产物）与预测结果进行了比较。
• Predicting the Most Favored Path and the Overall Rate of Multistep: 2-Norbornyl Cation Rearrangements. The Assignment of a Trial Activation Energy for Each Unique Step
  作者：R. Haseltine、E. Huang、K. Ranganayakulu、T. S. Sorensen、N. Wong

  DOI：10.1139/v75-263

  日期：1975.7.1

  Observable 2-norbornyl cations undergo at least five different rearrangement reactions, all of which are known from previous work on this system. In this paper, these rearrangement categories have been subdivided to reflect secondary–tertiary energy and rate differences and a trial set of activation free energies ΔG^≠ is derived for each subdivided step. The most important of these parameters is the energy difference between secondary and tertiary (methyl) systems which was estimated as 5.5 kcal/mol. These parameters allow one, for the first time, to make a rational assessment of the overall reaction course of multistep rearrangement reactions in this system, for example, those observed in a number of bicyclo[2.2.1]heptyl(norbornyl) terpene systems.

  可观察到的2-诺博烯基阳离子至少经历了五种不同的重排反应，这些反应都是从此系统的先前研究中所知道的。在本文中，这些重排类别已被细分以反映二级-三级能量和速率差异，并针对每个细分步骤推导出一组试验性的活化自由能ΔG≠。其中最重要的参数是二级和三级（甲基）系统之间的能量差，估计为5.5 kcal/mol。这些参数首次使得人们能够理性评估该系统中多步重排反应的整体反应过程，例如，在一些二环[2.2.1]庚基（诺博烯基）萜类化合物中观察到的反应。
• Buchbauer, Gerhard; Rohner, Helga Christiane, Liebigs Annalen der Chemie, 1981, # 11, p. 2093 - 2095
  作者：Buchbauer, Gerhard、Rohner, Helga Christiane

  DOI：——

  日期：——
• Pulkkinen, Annales Academiae Scientiarum Fennicae, Series A2: Chemica, 1956, # 74, p. 7,57, 82
  作者：Pulkkinen

  DOI：——

  日期：——
• Banert, Klaus; Kirmse, Wolfgang; Wroblowsky, Heinz-Juergen, Chemische Berichte, 1983, vol. 116, # 11, p. 3591 - 3610
  作者：Banert, Klaus、Kirmse, Wolfgang、Wroblowsky, Heinz-Juergen

  DOI：——

  日期：——