1-cyclohexyl-2-iodoethanol | 1258048-56-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 1-cyclohexyl-2-iodoethanol
• 英文别名: 1-cyclohexyl-2-iodoethan-1-ol
• CAS: 1258048-56-4
• 化学式: C₈H₁₅IO
• 分子量: 254.111
• InChiKey: SGLQWURDZKGUIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-cyclohexyl-2-iodoethanol 、 丙炔酸乙酯 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  Tandem SN2-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,5-tetrasubstituted tetrahydrofurans

  摘要：

  A stereoselective method for the synthesis of substituted tetrahydrofuran derivatives employing a tandem alkylation-Michael addition sequence to vinylogous carbonates is developed. The method could be used to synthesize THFs bearing tertiary ethers. Further, the method is extended to the synthesis of adjacent bis-THFs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.008
• 作为产物：
  描述：

  2-环己基环氧乙烷 在 sodium acetate 、 溶剂黄146 、 sodium iodide 作用下， 以74%的产率得到1-cyclohexyl-2-iodoethanol
  参考文献：
  名称：

  Tandem SN2-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,5-tetrasubstituted tetrahydrofurans

  摘要：

  A stereoselective method for the synthesis of substituted tetrahydrofuran derivatives employing a tandem alkylation-Michael addition sequence to vinylogous carbonates is developed. The method could be used to synthesize THFs bearing tertiary ethers. Further, the method is extended to the synthesis of adjacent bis-THFs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.008

文献信息

• Electrochemical Synthesis of Iodohydrins
  作者：Shinan Luan、Thomas Castanheiro、Thomas Poisson

  DOI：10.1002/adsc.202200470

  日期：2022.8.16

  Iodohydrins and corresponding ethers were synthesized by an electrochemical process using inexpensive and non-toxic ammonium iodide. This transformation was applied to a panel of alkenes, giving products without the need of external hazardous oxidants, reductants or metal catalyst. This protocol showed a general efficiency to synthesize valuable iodinated molecules with yields from 19% to 90%.

  使用廉价且无毒的碘化铵通过电化学方法合成碘醇和相应的醚。这种转变应用于一组烯烃，无需外部有害氧化剂、还原剂或金属催化剂即可得到产品。该协议显示了合成有价值的碘化分子的一般效率，产率从 19% 到 90%。
• Oxidative addition of trifluoromethanesulfonamide to vinylcyclohexane and p-chlorostyrene
  作者：B. A. Shainyan、M. Yu. Moskalik、V. V. Astakhova

  DOI：10.1134/s1070428012070056

  日期：2012.7

  Trifluoromethanesulfonamide reacted with vinylcyclohexane in the system t-BuOCl-NaI to give a mixture of 2,6-dicyclohexyl-1,4-bis(trifluoromethylsulfonyl)piperazine and 2-iodo-1-cyclohexylethanol. Conformational behavior of the heterocyclization product was studied by dynamic NMR. The reaction of p-chlorostyrene with trifluoromethanesulfonamide under analogous conditions produced the corresponding bis-adduct, N-[2-(4-chlorophenyl)-2-(trifluoromethylsulfonylamino)ethyl]trifluoromethanesulfonamide and 1-(4-chlorophenyl)-2-iodoethanol. A probable reaction mechanism was proposed, which rationalizes difference in the behavior of the examined alkenes.