cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine | 158009-37-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine
• 英文别名: methyl (2S,3S)-1-[(S)-(4-methylphenyl)sulfinyl]-3-phenylaziridine-2-carboxylate
• CAS: 158009-37-1
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: UMPUHHVBBMHJPU-AOHJGNDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以94%的产率得到cis-(2S,3S)-(+)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-phenylaziridine
  参考文献：
  名称：

  Aza-Darzens Asymmetric Synthesis of N-(p-Toluenesulfinyl)aziridine 2-Carboxylate Esters from Sulfinimines (N-Sulfinyl Imines)

  摘要：

  The one-step aza-Darzens reaction of sulfinimines 2 with lithium alpha-bromoenolates readily affords diversely substituted cis and trans N-sulfinylaziridine 2-carboxylate esters 3 and 7 in good yield and excellent diastereoselectivity. Higher yields, but lower de's, result when a mixture of the alpha-bromo ester and 2 are treated with base. The N-sulfinyl group is transformed, nearly quantitatively, without ring opening, into the N-tosyl activating group by oxidation with m-CPBA. Selective removal of the N-sulfinyl group in aziridines 3a and 3h with TFA/H2O affords VI-aziridines 21 which are difficult to prepared by other means. However, C(3) activated azirines such as 3b undergo ring-opening under these conditions. Alternatively, the N-sulfinyl group, even in C(3)-activated aziridines, was selectively and efficiently removed by treatment of the aziridine with 2 equiv of MeMgBr.

  DOI：

  10.1021/jo990907j
• 作为产物：
  描述：

  (S)-(+)-对甲基苯亚磺酰胺 在 四氢吡咯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine
  参考文献：
  名称：

  一种手性亚磺酰胺化合物及其制备方法和应用

  摘要：

  本发明提供了一种手性亚磺酰胺化合物及其制备方法和应用，涉及化合物合成领域，手性亚磺酰胺化合物的结构通式如式(1)所示。本发明公开了苯亚磺酸钠和胺在催化剂奎宁或奎尼丁的催化下高效的制备手性亚磺胺化合物及其衍生物，具有优异的产率、对映选择性高达99％及良好的应用潜力和研究价值。

  公开号：

  CN117383995A

文献信息

• Photodesulfinylation of optically active N-sulfinyl amines
  作者：Franklin A. Davis、Tokala Ramachandar、Yanfeng Zhang、Jing Chai、Hui Qiu、Jianghe Deng、Venkata Velvadapu

  DOI：10.1016/j.tetlet.2010.05.114

  日期：2010.8

  Photolysis of enantiopure N-sulfinyl amines (sulfinamides) in Et2O–MeOH gives amines in good yield without racemization.

  对映体纯的N-亚磺酰基胺（亚磺酰胺）在Et 2 O-MeOH中的光解得到的胺收率好，没有消旋作用。
• Aza-Darzens Asymmetric Synthesis of <i>N</i>-(<i>p</i>-Toluenesulfinyl)aziridine 2-Carboxylate Esters from Sulfinimines (<i>N</i>-Sulfinyl Imines)
  作者：Franklin A. Davis、Hu Liu、Ping Zhou、Tianan Fang、G. Venkat Reddy、Yulian Zhang

  DOI：10.1021/jo990907j

  日期：1999.10.1

  The one-step aza-Darzens reaction of sulfinimines 2 with lithium alpha-bromoenolates readily affords diversely substituted cis and trans N-sulfinylaziridine 2-carboxylate esters 3 and 7 in good yield and excellent diastereoselectivity. Higher yields, but lower de's, result when a mixture of the alpha-bromo ester and 2 are treated with base. The N-sulfinyl group is transformed, nearly quantitatively, without ring opening, into the N-tosyl activating group by oxidation with m-CPBA. Selective removal of the N-sulfinyl group in aziridines 3a and 3h with TFA/H2O affords VI-aziridines 21 which are difficult to prepared by other means. However, C(3) activated azirines such as 3b undergo ring-opening under these conditions. Alternatively, the N-sulfinyl group, even in C(3)-activated aziridines, was selectively and efficiently removed by treatment of the aziridine with 2 equiv of MeMgBr.
• 一种手性亚磺酰胺化合物及其制备方法和应用
  申请人：贵州大学

  公开号：CN117383995A

  公开（公告）日：2024-01-12

  本发明提供了一种手性亚磺酰胺化合物及其制备方法和应用，涉及化合物合成领域，手性亚磺酰胺化合物的结构通式如式(1)所示。本发明公开了苯亚磺酸钠和胺在催化剂奎宁或奎尼丁的催化下高效的制备手性亚磺胺化合物及其衍生物，具有优异的产率、对映选择性高达99％及良好的应用潜力和研究价值。