(NE,R)-N-[6-(4-methoxyphenyl)-6-oxohexylidene]-2-methylpropane-2-sulfinamide | 1174579-72-6

• 英文名称: (NE,R)-N-[6-(4-methoxyphenyl)-6-oxohexylidene]-2-methylpropane-2-sulfinamide
• CAS: 1174579-72-6
• 化学式: C₁₇H₂₅NO₃S
• 分子量: 323.456
• InChiKey: OQGJZPSTQZVREL-MKRMIXIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (NE,R)-N-[6-(4-methoxyphenyl)-6-oxohexylidene]-2-methylpropane-2-sulfinamide 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(R)-N-[(1S,2R)-2-hydroxy-2-(4-methoxyphenyl)cyclohexyl]-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  SmI₂-Promoted Intramolecular Asymmetric Pinacol-Type Ketone−tert-Butanesulfinyl Imine Reductive Coupling: Stereoselectivity and Mechanism

  摘要：

  The asymmetric ketone-tert-butanesulfinyl (t-BS) imine pinacol-type reductive coupling promoted by SmI2 is described. Trans-1,2-vicinal amino alcohols were formed predominantly in excellent er and high dr. The stereochemical outcome provided evidence for a radical mechanism for SmI2-induced reductive couplings of t-BS imines.

  DOI：

  10.1021/ol901296u
• 作为产物：
  描述：

  6-(4-methoxyphenyl)-6-oxohexanal 、 (R)-(+)-叔丁基亚磺酰胺 在 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 生成 (NE,R)-N-[6-(4-methoxyphenyl)-6-oxohexylidene]-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  SmI₂-Promoted Intramolecular Asymmetric Pinacol-Type Ketone−tert-Butanesulfinyl Imine Reductive Coupling: Stereoselectivity and Mechanism

  摘要：

  The asymmetric ketone-tert-butanesulfinyl (t-BS) imine pinacol-type reductive coupling promoted by SmI2 is described. Trans-1,2-vicinal amino alcohols were formed predominantly in excellent er and high dr. The stereochemical outcome provided evidence for a radical mechanism for SmI2-induced reductive couplings of t-BS imines.

  DOI：

  10.1021/ol901296u