(R_S,2R)-(-)-N-(tert-butanesulfinyl)-3,3-dipentyl-2-[(trimethylsilyl)ethynyl]aziridine | 813461-55-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (R_S,2R)-(-)-N-(tert-butanesulfinyl)-3,3-dipentyl-2-[(trimethylsilyl)ethynyl]aziridine
• 英文别名: 2-[(2R)-1-[(R)-tert-butylsulfinyl]-3,3-dipentylaziridin-2-yl]ethynyl-trimethylsilane
• CAS: 813461-55-1
• 化学式: C₂₁H₄₁NOSSi
• 分子量: 383.714
• InChiKey: KFNNLGQENADFOY-ZMLHKZHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  39.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R_S,2R)-(-)-N-(tert-butanesulfinyl)-3,3-dipentyl-2-[(trimethylsilyl)ethynyl]aziridine 在 盐酸 作用下， 以 甲醇 为溶剂， 以100%的产率得到(2R)-(+)-3,3-dipentyl-2-[(trimethylsilyl)ethynyl]aziridine
  参考文献：
  名称：

  High Kinetic Resolution in the Addition of a Racemic Allenylzinc onto Enantiopure N-tert-Butanesulfinimines:  Concise Synthesis of Enantiopure trans-2-Ethynylaziridines¹

  摘要：

  Enantiopure trans-ethynyl N-tert-butanesulfinylaziridines (R-s)-6 were prepared in good to excellent yields by the condensation of the racemic allenylzinc species 1 derived from 3-chloro-l-trimethyl-silylpropyne onto the corresponding enantiopure N-tert-butanesulfinimines (R-s)-5. The absolute stereochemistry of enantiopure N-tert-butanesulfinylaziridines (R-s)-6 was shown to be (R-s,2R,3R) and results from a chelate-type transition state in which the zinc atom of allenylzinc 1 is coordinated by both the nitogen and the oxygen atoms of the imine. Further removal of the N-tert-butanesulfinyl auxiliary of alkyl 3-substituted and 3,3-disubstituted ethynyl N-tert-butanesulfinylaziridines (Rs)-6 could be achieved by treatment with HCl in MeOH affording the corresponding deprotected aziridines (2R,3R)-9 and (2R)-9 respectively as enantiomerically pure compounds.

  DOI：

  10.1021/jo0490696
• 作为产物：
  描述：

  二正戊基酮 在 titanium(IV) tetraethanolate 、 magnesium sulfate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 22.0h， 生成 (R_S,2R)-(-)-N-(tert-butanesulfinyl)-3,3-dipentyl-2-[(trimethylsilyl)ethynyl]aziridine
  参考文献：
  名称：

  High Kinetic Resolution in the Addition of a Racemic Allenylzinc onto Enantiopure N-tert-Butanesulfinimines:  Concise Synthesis of Enantiopure trans-2-Ethynylaziridines¹

  摘要：

  Enantiopure trans-ethynyl N-tert-butanesulfinylaziridines (R-s)-6 were prepared in good to excellent yields by the condensation of the racemic allenylzinc species 1 derived from 3-chloro-l-trimethyl-silylpropyne onto the corresponding enantiopure N-tert-butanesulfinimines (R-s)-5. The absolute stereochemistry of enantiopure N-tert-butanesulfinylaziridines (R-s)-6 was shown to be (R-s,2R,3R) and results from a chelate-type transition state in which the zinc atom of allenylzinc 1 is coordinated by both the nitogen and the oxygen atoms of the imine. Further removal of the N-tert-butanesulfinyl auxiliary of alkyl 3-substituted and 3,3-disubstituted ethynyl N-tert-butanesulfinylaziridines (Rs)-6 could be achieved by treatment with HCl in MeOH affording the corresponding deprotected aziridines (2R,3R)-9 and (2R)-9 respectively as enantiomerically pure compounds.

  DOI：

  10.1021/jo0490696

文献信息

• High Kinetic Resolution in the Addition of a Racemic Allenylzinc onto Enantiopure <i>N</i>-<i>tert</i>-Butanesulfinimines:  Concise Synthesis of Enantiopure <i>trans</i>-2-Ethynylaziridines¹
  作者：Fabrice Chemla、Franck Ferreira

  DOI：10.1021/jo0490696

  日期：2004.11.1

  Enantiopure trans-ethynyl N-tert-butanesulfinylaziridines (R-s)-6 were prepared in good to excellent yields by the condensation of the racemic allenylzinc species 1 derived from 3-chloro-l-trimethyl-silylpropyne onto the corresponding enantiopure N-tert-butanesulfinimines (R-s)-5. The absolute stereochemistry of enantiopure N-tert-butanesulfinylaziridines (R-s)-6 was shown to be (R-s,2R,3R) and results from a chelate-type transition state in which the zinc atom of allenylzinc 1 is coordinated by both the nitogen and the oxygen atoms of the imine. Further removal of the N-tert-butanesulfinyl auxiliary of alkyl 3-substituted and 3,3-disubstituted ethynyl N-tert-butanesulfinylaziridines (Rs)-6 could be achieved by treatment with HCl in MeOH affording the corresponding deprotected aziridines (2R,3R)-9 and (2R)-9 respectively as enantiomerically pure compounds.