trans 2-α-iodo-4-t-butyl-cyclohexanone | 77299-79-7

• 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: trans 2-α-iodo-4-t-butyl-cyclohexanone
• 英文别名: trans-4-tert-butyl-2-iodo-cyclohexanone；trans-2-iodo-4-tert-butylcyclohexanone；trans-4-tert-Butyl-2-iodocyclohexanone；4-tert-butyl-2-iodocyclohexanone
• CAS: 77299-79-7
• 化学式: C₁₀H₁₇IO
• 分子量: 280.149
• InChiKey: JHCZXVWLDIJNQA-SFYZADRCSA-N

物化性质

• 沸点：
  283.4±33.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-(叔丁基)-1-环己烯 在 重铬酸吡啶 、 molecular sieve 、 碘 作用下， 生成 trans 2-α-iodo-4-t-butyl-cyclohexanone
  参考文献：
  名称：

  有机合成中的重铬酸吡啶鎓：将烯烃-碘络合物轻松氧化为α-碘酮

  摘要：

  环状α-碘酮可通过用重铬酸吡啶鎓氧化烯烃-碘络合物直接获得。

  DOI：

  10.1016/s0040-4039(00)74539-4

文献信息

• Iodination of Enol Acetates and 1,3-Diones Using<i>N</i>-Iodosaccharin
  作者：Darko Dolenc

  DOI：10.1081/scc-120022182

  日期：2003.1.8

  Abstract Iodination of enol acetates and 1,3-diones with N-iodosaccharin yielding the corresponding α-iodoketones and 2-iodo-1,3-diones is presented. Reactions are carried out at room temperature under neutral conditions and in short reaction times.

  摘要 介绍了用 N-碘糖精对烯醇乙酸酯和 1,3-二酮进行碘化，产生相应的 α-碘酮和 2-碘-1,3-二酮。反应在室温、中性条件和短反应时间内进行。
• Aerobic oxidative iodination of ketones catalysed by sodium nitrite “on water” or in a micelle-based aqueous system
  作者：Gaj Stavber、Jernej Iskra、Marko Zupan、Stojan Stavber

  DOI：10.1039/b902230a

  日期：——

  oxidative iodination of ketones in aqueous media was achieved by using molecular iodine as the source of iodine atoms, air as the terminal oxidant, sodium nitrite (NaNO2) as the catalyst and H2SO4 as the activator of the overall catalytic process. The efficiency of the reaction, resulting in α-iodo ketones, was significantly improved in an aqueous solution of the anionic amphiphile sodium dodecyl sulfate (SDS)

  选择性和有效的好氧氧化 碘化 分子筛分析水介质中酮的含量 碘 作为 碘 原子，空气作为终端氧化剂， 亚硝酸钠（NaNO 2）作为催化剂和H 2 SO 4作为整体的活化剂催化过程。在阴离子水溶液中，产生α-碘酮的反应效率显着提高。两亲的 十二烷基硫酸钠 （SDS），能够 自组装形成基于胶束的聚集体，从而形成反应性胶束系统。芳基甲基酮碘官能化的区域选择性受所用反应介质的调节：在基于胶束的水性体系中，甲基 碘化，而在无水MeCN中形成的芳基碘具有高选择性。
• Aerobic oxidative α-iodination of carbonyl compounds using molecular iodine activated by a nitrate-based catalytic system
  作者：Rok Prebil、Stojan Stavber

  DOI：10.1016/j.tetlet.2014.08.055

  日期：2014.10

  The novel reaction system comprising air/NH4NO3(cat.)/I-2/H2SO4(cat.) is introduced as a simple, safe, cheap, efficient, and regioselective mediator for direct aerobic oxidative a-iodination of aryl, heteroaryl, alkyl, and cycloallcyl methyl ketones. The reaction system enabled the moderate to quantitative regioselective iodination of a large range of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents. Several activated aromatic compounds were also efficiently and selectively iodinated. The practical applicability of the presented reaction system was shown on 20 mmol scale under ambient pressure and 100% conversion of substrate was achieved. (C) 2014 Elsevier Ltd. All rights reserved.
• Syntheses of α-lodocarbonyl Compounds Using Bis(<i>sym</i>-collidine)lodine(I) Tetrafluoroborate/Dimethyl Sulfoxide
  作者：Robert D. Evans、J. Herman Schauble

  DOI：10.1055/s-1986-31757

  日期：——
• Axial/equatorial proportions for 2-substituted cyclohexanones
  作者：Ernani A. Basso、Carlos Kaiser、Roberto Rittner、Joseph B. Lambert

  DOI：10.1021/jo00079a035

  日期：1993.12

  Axial-equatorial conformational proportions have been measured for 2-substituted cyclohexanones in chloroform by the Eliel method for F, Cl, Br, I, MeO, MeS, Me2N, MeSe, and Me. For the first seven of these, at least five experimentally independent measurables were used and the resulting conformational preferences appear to be accurate to within 10%. Systematic errors degraded the results for MeSe and Me. For Me2N, the conformational preference also was measured for the first time at slow exchange in the low-temperature C-13 spectrum in several solvents. In chloroform, steric and polar effects contribute to the conformational preferences, with steric effects dominant for large groups such as I and MeS.