diethyl (S_S,2S,3R)-(+)-N-(mesitylsulfinyl)-3-phenylaziridine-2-phosphonate | 607729-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: diethyl (S_S,2S,3R)-(+)-N-(mesitylsulfinyl)-3-phenylaziridine-2-phosphonate
• 英文别名: (2S,3R)-2-diethoxyphosphoryl-3-phenyl-1-[(S)-(2,4,6-trimethylphenyl)sulfinyl]aziridine
• CAS: 607729-55-5
• 化学式: C₂₁H₂₈NO₄PS
• 分子量: 421.497
• InChiKey: FMAYPRRCBHSVNO-YGXSNNNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (S_S,2S,3R)-(+)-N-(mesitylsulfinyl)-3-phenylaziridine-2-phosphonate 在 甲基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 以77%的产率得到diethyl (2S,3R)-(-)-3-phenylaziridine-2-phosphonate
  参考文献：
  名称：

  Improved Asymmetric Synthesis of Aziridine 2-Phosphonates Using (S)-(+)-2,4,6-Trimethylphenylsulfinamide

  摘要：

  The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-aziridine 2-phosphonate chiral building blocks. An improved asymmetric synthesis of (S)-(+)-2,4,6-trimethylphenylsulfinamide is also given.

  DOI：

  10.1021/jo030142m
• 作为产物：
  描述：

  (R_S,1S,2R)-(-)-2,4,6-trimethylbenzenesulfinic acid 1-(2,4,6-trimethylbenzenesulfonylamino)indan-2-yl ester 在 titanium(IV) tetraethanolate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 diethyl (S_S,2S,3R)-(+)-N-(mesitylsulfinyl)-3-phenylaziridine-2-phosphonate
  参考文献：
  名称：

  Improved Asymmetric Synthesis of Aziridine 2-Phosphonates Using (S)-(+)-2,4,6-Trimethylphenylsulfinamide

  摘要：

  The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-aziridine 2-phosphonate chiral building blocks. An improved asymmetric synthesis of (S)-(+)-2,4,6-trimethylphenylsulfinamide is also given.

  DOI：

  10.1021/jo030142m

文献信息

• Improved Asymmetric Synthesis of Aziridine 2-Phosphonates Using (<i>S</i>)-(+)-2,4,6-Trimethylphenylsulfinamide
  作者：Franklin A. Davis、Tokala Ramachandar、Yongzhong Wu

  DOI：10.1021/jo030142m

  日期：2003.9.1

  The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-aziridine 2-phosphonate chiral building blocks. An improved asymmetric synthesis of (S)-(+)-2,4,6-trimethylphenylsulfinamide is also given.