1-碘双环[2.2.2]辛烷 | 931-98-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 中文名称: 1-碘双环[2.2.2]辛烷
• 英文名称: 1-Iodobicyclo<2.2.2>octane
• 英文别名: 1-I-bicyclo<2.2.2>octane；1-iodobicyclo[2.2.2]octane；1-iodobicyclo{2.2.2}octane；1-Iod-bicyclo<2.2.2>octan；1-Jod-bicyclo<2.2.2>octan；1-Jodobicyclo<2.2.2>octan
• CAS: 931-98-6
• 化学式: C₈H₁₃I
• 分子量: 236.096
• InChiKey: SMDJHIPXLFNPTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  3.0
• 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：

  1-碘双环[2.2.2]辛烷 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到1-溴双环[2.2.2]辛烷
  参考文献：
  名称：

  Reactions of some bicycloalkyl iodides with bromine

  摘要：

  DOI：

  10.1021/jo00135a007
• 作为产物：
  描述：

  1,4-二氯双环[2.2.2]辛烷 在 氢氧化钾 、 aluminum tri-bromide 、 氢碘酸 、 叔丁基锂 、 silver(I) acetate 、 碘乙烷 作用下， 以 甲醇 、 乙醚 、 溶剂黄146 、 正戊烷 为溶剂， 反应 6.0h， 生成 1-碘双环[2.2.2]辛烷
  参考文献：
  名称：

  Rod-like organic molecules. Energy-transfer studies using single-photon counting

  摘要：

  DOI：

  10.1021/jo01308a001

文献信息

• Photoinduced Copper‐Catalyzed Coupling of Terminal Alkynes and Alkyl Iodides
  作者：Avijit Hazra、Mitchell T. Lee、Justin F. Chiu、Gojko Lalic

  DOI：10.1002/anie.201801085

  日期：2018.5.4

  We have developed a photoinduced copper‐catalyzed alkylation of terminal alkynes with primary, secondary, or tertiary alkyl iodides as electrophiles. The reaction has a broad substrate scope and can be successfully performed in the presence of ester, nitrile, aryl halide, ketone, sulfonamide, epoxide, alcohol, and amide functional groups. The alkylation is promoted by blue light (λ≈450 nm) and proceeds

  我们已经开发出了以伯，仲或叔烷基碘为亲电试剂的末端炔烃的光诱导铜催化烷基化反应。该反应具有广泛的底物范围，并且可以在酯，腈，卤代芳基，酮，磺酰胺，环氧化物，醇和酰胺官能团的存在下成功进行。该烷基化是由蓝色光促进（λ ≈450nm）与在没有任何附加的金属催化剂的室温下进行。联吡啶配体的使用对于反应的成功至关重要，而且可以防止光诱导的铜催化原料的聚合。
• Photochemistry of alkyl halides. 4. 1-Norbornyl, 1-norbornylmethyl, 1- and 2-adamantyl, and 1-octyl bromides and iodides
  作者：Paul J. Kropp、Graham S. Poindexter、Norbert J. Pienta、David C. Hamilton

  DOI：10.1021/ja00441a043

  日期：1976.12

  Competing ionic and radical photobehavior has been observed for a number of alkyl halides. The proportion of nucleophilic substitution and reduction products were reported for each halide. Solvent effects of ethylene glycol, triethylamine, and methanol and atmospheric effects of nitrogen, oxygen, and air were studied. The effect of irradiation of the halides with methanol-O-d was reported. The results

  已经观察到许多卤代烷具有竞争性的离子和自由基光行为。报告了每种卤化物的亲核取代和还原产物的比例。研究了乙二醇、三乙胺和甲醇的溶剂效应以及氮气、氧气和空气的大气效应。报告了用甲醇-Od 辐照卤化物的效果。根据碳 - 卤素键的初始均裂以提供自由基对来讨论结果，该自由基对经历竞争性扩散和夺氢以产生还原产物和电子转移以提供离子对。离子对反过来产生取代和消除产物。(DDA)
• Synthesis of bridgehead fluorides by fluorodeiodination
  作者：Ernest W. Della、Nicholas J. Head

  DOI：10.1021/jo00036a018

  日期：1992.5

  Fluorodeiodination is found to be an attractive procedure for the synthesis of bridgehead fluorides. Thus, treatment of the corresponding iodide with xenon difluoride in dichloromethane at ambient temperature generally leads to high yields of the fluoride. Evidence suggests the intermediacy of the bridgehead cation in this reaction, and accordingly the substrates which are unfavorably disposed to fluorodeiodination are the bicyclo[n.1.1]alkyl iodides. In this context the isolation of a small quantity of methyl 4-fluorobicyclo[2.1.1]hexane-1-carboxylate (46, R = COOMe) is significant because it represents the first occasion on which the elusive 1-bicyclo[2.1.1]hexyl cation has been trapped. We have also demonstrated that synthesis of the iodides themselves can be accomplished efficiently both by Barton halodecarboxylation and by treatment of the carboxylic acid with lead tetraacetate and iodine.
• Kopecky, Jan; Smejkal, Jaroslav, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 11, p. 2965 - 2970
  作者：Kopecky, Jan、Smejkal, Jaroslav

  DOI：——

  日期：——
• Bridged ring compounds. VIII. 1-Halobicyclo[2.2.-2]octanes
  作者：Zennosuke Suzuki、Kenichi Morita

  DOI：10.1021/jo01277a008

  日期：1967.1

表征谱图