N-[(E)-cyclohex-3-en-1-ylmethylidene]-4-methylbenzenesulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(E)-cyclohex-3-en-1-ylmethylidene]-4-methylbenzenesulfonamide
• 英文别名: (NE)-N-(cyclohex-3-en-1-ylmethylidene)-4-methylbenzenesulfonamide
• 化学式: C₁₄H₁₇NO₂S
• 分子量: 263.36
• InChiKey: XWXSGTGESUUJGC-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碘甲烷 、 N-[(E)-cyclohex-3-en-1-ylmethylidene]-4-methylbenzenesulfonamide 在 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.66h， 生成 cis-(±)-2-iodo-3-(cyclohex-3-en-1-yl)-1-(4-tolylsulfonyl)aziridine 、 cis-(±)-2-iodo-3-(cyclohex-3-en-1-yl)-1-(4-tolylsulfonyl)aziridine
  参考文献：
  名称：

  Synthesis of cis-C-Iodo-N-Tosyl-Aziridines using Diiodomethyllithium: Reaction Optimization, Product Scope and Stability, and a Protocol for Selection of Stationary Phase for Chromatography

  摘要：

  The preparation of C-iodo-N-Ts-aziridines with excellent cis-diastereoselectivity has been achieved in high yields by the addition of diiodomethyllithium to N-tosylimines and N-tosylimine-HSO(2)Tol adducts. This addition-cyclization protocol successfully provided a wide range of cis-iodoaziridines, including the first examples of alkyl-substituted iodoaziridines, with the reaction tolerating both aryl imines and alkyl imines. An ortho-chlorophenyl imine afforded a beta-amino gem-diiodide under the optimized reaction conditions due to a postulated coordinated intermediate preventing cyclization. An effective protocol to assess the stability of the sensitive iodoaziridine functional group to chromatography was also developed. As a result of the judicious choice of stationary phase, the iodoaziridines could be purified by column chromatography; the use of deactivated basic alumina (activity IV) afforded high yield and purity. Rearrangements of electron rich aryl-iodoaziridines have been promoted, selectively affording either novel alpha-iodo-N-Ts-imines or alpha-iodo-aldehydes in high yield.

  DOI：

  10.1021/jo400956x
• 作为产物：
  描述：

  3-环己烯甲醛 在 碳酸氢钠 作用下， 以 甲酸 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 N-[(E)-cyclohex-3-en-1-ylmethylidene]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis of cis-C-Iodo-N-Tosyl-Aziridines using Diiodomethyllithium: Reaction Optimization, Product Scope and Stability, and a Protocol for Selection of Stationary Phase for Chromatography

  摘要：

  The preparation of C-iodo-N-Ts-aziridines with excellent cis-diastereoselectivity has been achieved in high yields by the addition of diiodomethyllithium to N-tosylimines and N-tosylimine-HSO(2)Tol adducts. This addition-cyclization protocol successfully provided a wide range of cis-iodoaziridines, including the first examples of alkyl-substituted iodoaziridines, with the reaction tolerating both aryl imines and alkyl imines. An ortho-chlorophenyl imine afforded a beta-amino gem-diiodide under the optimized reaction conditions due to a postulated coordinated intermediate preventing cyclization. An effective protocol to assess the stability of the sensitive iodoaziridine functional group to chromatography was also developed. As a result of the judicious choice of stationary phase, the iodoaziridines could be purified by column chromatography; the use of deactivated basic alumina (activity IV) afforded high yield and purity. Rearrangements of electron rich aryl-iodoaziridines have been promoted, selectively affording either novel alpha-iodo-N-Ts-imines or alpha-iodo-aldehydes in high yield.

  DOI：

  10.1021/jo400956x

文献信息

• Synthesis of <i>cis</i>-<i>C</i>-Iodo<i>-N</i>-Tosyl-Aziridines using Diiodomethyllithium: Reaction Optimization, Product Scope and Stability, and a Protocol for Selection of Stationary Phase for Chromatography
  作者：Tom Boultwood、Dominic P. Affron、Aaron D. Trowbridge、James A. Bull

  DOI：10.1021/jo400956x

  日期：2013.7.5

  The preparation of C-iodo-N-Ts-aziridines with excellent cis-diastereoselectivity has been achieved in high yields by the addition of diiodomethyllithium to N-tosylimines and N-tosylimine-HSO(2)Tol adducts. This addition-cyclization protocol successfully provided a wide range of cis-iodoaziridines, including the first examples of alkyl-substituted iodoaziridines, with the reaction tolerating both aryl imines and alkyl imines. An ortho-chlorophenyl imine afforded a beta-amino gem-diiodide under the optimized reaction conditions due to a postulated coordinated intermediate preventing cyclization. An effective protocol to assess the stability of the sensitive iodoaziridine functional group to chromatography was also developed. As a result of the judicious choice of stationary phase, the iodoaziridines could be purified by column chromatography; the use of deactivated basic alumina (activity IV) afforded high yield and purity. Rearrangements of electron rich aryl-iodoaziridines have been promoted, selectively affording either novel alpha-iodo-N-Ts-imines or alpha-iodo-aldehydes in high yield.