(2R,3S)-2-iodo-1-[(R)-2-methylpropane-2-sulfinyl]-3-phenylaziridine | 1443767-59-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R,3S)-2-iodo-1-[(R)-2-methylpropane-2-sulfinyl]-3-phenylaziridine
• 英文别名: (2R,3S)-1-[(R)-tert-butylsulfinyl]-2-iodo-3-phenylaziridine
• CAS: 1443767-59-6
• 化学式: C₁₂H₁₆INOS
• 分子量: 349.236
• InChiKey: GOPJXKOAUGWEDA-KZTITWOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 在 titanium(IV) tetraethanolate 、 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 24.66h， 生成 (2R,3S)-2-iodo-1-[(R)-2-methylpropane-2-sulfinyl]-3-phenylaziridine 、 (2S,3R)-2-iodo-1-[(R)-2-methylpropane-2-sulfinyl]-3-phenylaziridine
  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

• Studies on the synthesis of α-iodoaziridines and improved conditions for the synthesis of alkyl-α-iodoaziridines using ClMgCHI2
  作者：Tom Boultwood、Dominic P. Affron、James A. Bull

  DOI：10.1016/j.tet.2015.05.098

  日期：2015.7

  The effects of varying the N-group and using different carbenoids are investigated. Excellent cis-stereochemistry is achieved, except for N-carbamates containing aryl groups. Using the mixed carbenoid LiCHICl, the iodide leaving group is selected for cyclisation affording chloroaziridines only, as a cis/trans mixture. More convenient and higher yielding conditions for the preparation of alkyl N-Ts α-iodoaziridines

  α-碘氮丙啶是完整的氮丙啶进一步功能化的不寻常的基序和有趣的结构。通过LiCHI 2与亚胺的加成环化反应可实现N保护的α-碘氮丙啶的制备。研究了改变N-基团和使用不同类胡萝卜素的影响。除了含有芳基的N-氨基甲酸酯以外，还可以实现优异的顺式立体化学。使用混合的类胡萝卜素LiCHICl，选择碘化物离去基团进行环化，仅提供氯氮丙啶，为顺式/反式混合物。制备烷基氮更方便，收率更高-Ts使用ClMgCHI 2开发了α-碘氮丙啶。另外，实现了有问题的伯烷基α-碘氮丙啶的形成。