(1S,1'S)-N-(2-Hydroxy-1-isopropylethyl)-o-(1'-hydroxy-1'-phenylmethyl)-N-methylbenzenesulfonamide | 134295-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,1'S)-N-(2-Hydroxy-1-isopropylethyl)-o-(1'-hydroxy-1'-phenylmethyl)-N-methylbenzenesulfonamide
• 英文别名: N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-2-[(S)-hydroxy(phenyl)methyl]-N-methylbenzenesulfonamide
• CAS: 134295-45-7
• 化学式: C₁₉H₂₅NO₄S
• 分子量: 363.478
• InChiKey: XLOGBUVGCYDGIB-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-N-(2'-Hydroxy-1'-isopropylethyl)-N-methylbenzenesulfonamide 、 苯甲醛 在 正丁基锂 作用下， 生成 (1S,1'R)-N-(2-Hydroxy-1-isopropylethyl)-o-(1'-hydroxy-1'-phenylmethyl)-N-methylbenzenesulfonamide 、 (1S,1'S)-N-(2-Hydroxy-1-isopropylethyl)-o-(1'-hydroxy-1'-phenylmethyl)-N-methylbenzenesulfonamide
  参考文献：
  名称：

  The remarkable effect of titanium tetraisopropoxide in diastereoselective reaction of carbaldehydes with chiral benzenesulfonamide lithium complexes.

  摘要：

  通过用四异丙氧基钛处理锂络合物（2和6）制备手性苯磺酰胺钛酸酯络合物（4和8）。芳香族甲醛与4和8进行非对映选择性反应，得到手性邻-(1-芳基-1-羟甲基)苯磺酰胺(3a-d和7a-e)，收率80-87%。这些产品的非对映体过量 (d.e.) 经评估为 62-82%。这些化合物也是由锂配合物（2 和 6）制备的，但 d.e.在这种情况下，该值仅为 6-14%。

  DOI：

  10.1248/cpb.39.260

文献信息

• The remarkable effect of titanium tetraisopropoxide in diastereoselective reaction of carbaldehydes with chiral benzenesulfonamide lithium complexes.
  作者：Hiroshi TAKAHASHI、Takeshi TSUBUKI、Kimio HIGASHIYAMA

  DOI：10.1248/cpb.39.260

  日期：——

  Chiral benzenesulfonamide titanium ate-complexes (4 and 8) were prepared from the lithium complexes (2 and 6) by treatment with titanium tetraisopropoxide. The diastereoselective reactions of aromatic carbaldehydes with 4 and 8 were performed, and the chiral o-(1-aryl-1-hydroxymethyl)benzenesulfonamides (3a-d and 7a-e) were obtained in 80-87% yields. The diastereomeric excesses (d.e.) of these products were evaluated as 62-82%. These compounds were also prepared from the lithium complexes (2 and 6), but the d.e. values were only 6-14% in this case.

  通过用四异丙氧基钛处理锂络合物（2和6）制备手性苯磺酰胺钛酸酯络合物（4和8）。芳香族甲醛与4和8进行非对映选择性反应，得到手性邻-(1-芳基-1-羟甲基)苯磺酰胺(3a-d和7a-e)，收率80-87%。这些产品的非对映体过量 (d.e.) 经评估为 62-82%。这些化合物也是由锂配合物（2 和 6）制备的，但 d.e.在这种情况下，该值仅为 6-14%。