(R_S)-(-)-N-α-pentylhexylidene-tert-butanesulfinamide | 813461-48-2

• 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)-(-)-N-α-pentylhexylidene-tert-butanesulfinamide
• 英文别名: (R)-2-methyl-N-undecan-6-ylidenepropane-2-sulfinamide
• CAS: 813461-48-2
• 化学式: C₁₅H₃₁NOS
• 分子量: 273.483
• InChiKey: DBJFPLTUBWOGEW-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R_S)-(-)-N-α-pentylhexylidene-tert-butanesulfinamide 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 (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 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 、 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以82%的产率得到(R_S)-(-)-N-α-pentylhexylidene-tert-butanesulfinamide
  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

• Allenylzincs and tert-butylsulfinylimines: a fruitful marriage for synthesis
  作者：Candice Botuha、Fabrice Chemla、Franck Ferreira、Julien Louvel、Alejandro Pérez-Luna

  DOI：10.1016/j.tetasy.2010.04.044

  日期：2010.5

  2-amino alcohols by the addition of 3-chloro- and 3-methoxymethoxy- allenylzincs to chiral tert-butylsulfinylimines is described. The methodology is applicable to the preparation of alkynyl 2-amino-1,3-diols (O,N,O stereotriads) using α-alkoxy tert-butylsulfinylimines as chiral starting materials. The scope and limitations of the methodology along with recent applications to the efficient asymmetric syntheses

  描述了通过将3-氯-和3-甲氧基甲氧基-烯丙基锌锌添加到手性叔丁基亚磺酰亚胺中的炔基1,2-氨基醇的立体选择性合成。该方法适用于使用α-烷氧基叔丁基亚磺酰亚胺的手性原料制备炔基2-氨基-1,3-二醇（O，N，O立体三单元）。介绍了该方法的范围和局限性，以及对天然和/或生物活性生物碱和多羟基化生物碱的有效不对称合成的最新应用。
• 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.