trans-di-isopropylaziridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丙烷
• 英文名称: trans-di-isopropylaziridine
• 英文别名: (2S,3S)-2,3-di(propan-2-yl)aziridine
• 化学式: C₈H₁₇N
• 分子量: 127.23
• InChiKey: SGIOKISJHGLFFY-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 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：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-di-isopropylaziridine 在 4-二甲氨基吡啶 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S,3R)-1-((2R,3R)-2,3-Diisopropyl-aziridin-1-yl)-3-hydroxy-2-methyl-pentan-1-one
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0
• 作为产物：
  描述：

  trans-2,5-dimethyl-3-hexene epoxide 在 sodium azide 、 氯化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 丙醇 、 水 为溶剂， 反应 3.5h， 生成 trans-di-isopropylaziridine
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0

文献信息

• Stereospecific conversion of olefins into aziridines by p-tolyl-sulphonylhydroxylamine
  作者：Jeffrey C. Bottaro

  DOI：10.1039/c39800000560

  日期：——

  The reactions of O-p-tolylsulphonylhydroxylamine with olefins proceed stereospecifically to give aziridines in moderate to high yield.

  的反应Ø - p -tolylsulphonylhydroxylamine与烯烃进行立体专一性，以高产给予氮丙啶适度。
• On the use of C2-symmetric aziridines as chiral auxiliaries
  作者：David Tanner、Carin Birgersson、Adolf Gogoll、Kristina Luthman

  DOI：10.1016/s0040-4020(01)85546-0

  日期：1994.1

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.