2-吖丙啶丁醛,1-[(4-甲基苯基)磺酰]- | 166194-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-吖丙啶丁醛,1-[(4-甲基苯基)磺酰]-
• 英文名称: 4-[1-(toluene-4-sulfonyl)aziridin-2-yl]butyraldehyde
• 英文别名: 4-[1-(4-Methylbenzene-1-sulfonyl)aziridin-2-yl]butanal；4-[1-(4-methylphenyl)sulfonylaziridin-2-yl]butanal
• CAS: 166194-79-2
• 化学式: C₁₃H₁₇NO₃S
• 分子量: 267.349
• InChiKey: CCAJARDBFCFNRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-吖丙啶丁醛,1-[(4-甲基苯基)磺酰]- 在 lithium iodide 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 30.0h， 生成 rac-1-((1R,5S,6R)-8-tosyl-8-azabicyclo[3.2.1]octan-6-yl)ethan-1-one
  参考文献：
  名称：

  碘化物介导的 [3 + 2]-环加成反应与N-甲苯磺酰氮丙啶和 α,β-不饱和酮

  摘要：

  N-甲苯磺酰基氮丙啶和α,β-不饱和酮之间的[3+2]-环加成反应用碘化锂促进。该反应在温和条件下进行以提供N-甲苯磺酰基吡咯烷。以高产率提供了含四元碳的 3,3-二取代吡咯烷，包括螺环化合物。一个简单的程序和易于处理的试剂使这个反应简洁。该反应的分子内形式用于合成托烷骨架。

  DOI：

  10.1021/acs.joc.1c00532
• 作为产物：
  描述：

  1,5-已二烯 在 9-borabicyclo[3.3.1]nonane dimer 、 三氧化硫吡啶 、 copper(II) bis(trifluoromethanesulfonate) 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 9.25h， 生成 2-吖丙啶丁醛,1-[(4-甲基苯基)磺酰]-
  参考文献：
  名称：

  Synthesis and Reactivity of Azapalladacyclobutanes

  摘要：

  N-Sulfonyl aziridines undergo oxidative addition to palladium(0) complexes generated in situ from mixtures of Pd-2(dba)(3) and 1,10-phenanthroline. The resulting azapalladacyclobutane complexes undergo intramolecular carbopalladation in the presence of copper(I) iodide to afford azapalladabicyclo-[3.2.1] octanes. A deuterium-labeling experiment indicates that the oxidative addition proceeds via S(N)2-type attack of palladium(0) on the less-hindered carbon of the aziridine ring and that alkene insertion occurs in a syn fashion. The azapalladabicyclo[3.2.1] octane complexes undergo oxidative palladium-carbon bond functionalization in the presence of copper(II) bromide.

  DOI：

  10.1021/ja0660756

文献信息

• The synthesis of γ-amino olefins. A novel intramolecular aziridine — allylsilane reaction
  作者：Stephen C. Bergmeier、Punit P. Seth

  DOI：10.1016/0040-4039(95)00608-f

  日期：1995.5

  An intramolecular reaction of aziridines with allylsilanes has stereoselectively produced disubstituted cyclopentanes and cyclohexanes containing the γ-amino olefin unit.

  氮丙啶与烯丙基硅烷的分子内反应已经立体选择性地产生了含有γ-氨基烯烃单元的二取代的环戊烷和环己烷。
• Construction of Bridged Aza- and Oxa-[<i>n</i>.2.1] Skeletons via an Intramolecular Formal [3+2] Cycloaddition of Aziridines and Epoxides with Electron-Deficient Alkenes
  作者：Siyang Xing、Yuhan Wang、Changkun Jin、Shaochen Shi、Yihui Zhang、Ziya Liao、Kui Wang、Bolin Zhu

  DOI：10.1021/acs.joc.2c00287

  日期：2022.5.6

  intramolecular formal [3+2] cycloaddition of activated aziridines and epoxides with electron-deficient alkene has been developed for the general and efficient construction of bridged aza- and oxa-[n.2.1] (n = 3 or 4) skeletons. This strategy can be efficiently promoted by lithium iodide. To demonstrate its potential, the intramolecular formal [3+2] cycloaddition was used to access the important intermediate of homoepiboxidine

  已经开发了活化氮丙​​啶和环氧化物与缺电子烯烃的分子内形式 [3+2] 环加成，用于一般和有效地构建桥连氮杂-和氧杂-[ n .2.1]（n = 3 或 4）骨架。碘化锂可以有效地促进这一策略。为了证明其潜力，分子内形式的 [3+2] 环加成被用于获得高哌啶醇的重要中间体。
• Iodide-Mediated [3 + 2]-Cycloaddition Reaction with <i>N</i>-Tosylaziridines and α,β-Unsaturated Ketones
  作者：Yuya Nakagawa、Keigo Yamaguchi、Seijiro Hosokawa

  DOI：10.1021/acs.joc.1c00532

  日期：2021.6.4

  [3 + 2]-cycloaddition reaction between N-tosylaziridines and α,β-unsaturated ketones was promoted with lithium iodide. The reaction proceeded under mild conditions to provide N-tosylpyrrolidines. Quaternary carbon-possessing 3,3-disubstituted pyrrolidines including spiro compounds were afforded in high yields. A simple procedure with easy to handle reagents makes this reaction concise. The intramolecular

  N-甲苯磺酰基氮丙啶和α,β-不饱和酮之间的[3+2]-环加成反应用碘化锂促进。该反应在温和条件下进行以提供N-甲苯磺酰基吡咯烷。以高产率提供了含四元碳的 3,3-二取代吡咯烷，包括螺环化合物。一个简单的程序和易于处理的试剂使这个反应简洁。该反应的分子内形式用于合成托烷骨架。
• Synthesis and Reactivity of Azapalladacyclobutanes
  作者：Joshua E. Ney、John P. Wolfe

  DOI：10.1021/ja0660756

  日期：2006.12.1

  N-Sulfonyl aziridines undergo oxidative addition to palladium(0) complexes generated in situ from mixtures of Pd-2(dba)(3) and 1,10-phenanthroline. The resulting azapalladacyclobutane complexes undergo intramolecular carbopalladation in the presence of copper(I) iodide to afford azapalladabicyclo-[3.2.1] octanes. A deuterium-labeling experiment indicates that the oxidative addition proceeds via S(N)2-type attack of palladium(0) on the less-hindered carbon of the aziridine ring and that alkene insertion occurs in a syn fashion. The azapalladabicyclo[3.2.1] octane complexes undergo oxidative palladium-carbon bond functionalization in the presence of copper(II) bromide.