ethyl N-(4-methoxyphenyl)sulfonylethanimidate | 1298087-39-4

• 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: ethyl N-(4-methoxyphenyl)sulfonylethanimidate
• CAS: 1298087-39-4
• 化学式: C₁₁H₁₅NO₄S
• 分子量: 257.31
• InChiKey: RLWQZFDYZOXVKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl tert-butyldimethylsilylglyoxylate 、 (R_S,E)-­2-methyl-N­-(thiophen­-2­-ylmethylene)propane-2-sulfinamide 、 ethyl N-(4-methoxyphenyl)sulfonylethanimidate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙基苯 为溶剂， 反应 5.5h， 以86%的产率得到tert-butyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[(4-methoxyphenyl)sulfonylamino]-2-thiophen-2-yl-2,4-dihydropyrrole-3-carboxylate
  参考文献：
  名称：

  Three-Component Reactions of Sulfonylimidates, Silyl Glyoxylates and N-tert-Butanesulfinyl Aldimines: An Efficient, Diastereoselective, and Enantioselective Synthesis of Cyclic N-Sulfonylamidines

  摘要：

  Three-component coupling reactions of sulfonylimidates, silyl glyoxylates and N-tert-butanesulfinyl aldimines efficiently provide cyclic N-sulfonylamiclines containing free endocyclic N-H. The formation of two C-C bonds (contiguous stereogenic carbons), one O-Si bond, and one C-N bond, together with the cleavage of the chiral auxiliary (tert-butanesulfinyl group), occurs with excellent chemoselectivity, diastereoselectivity, and enantioselectivity in this one-pot cascade transformation.

  DOI：

  10.1021/ol201029b
• 作为产物：
  描述：

  对甲氧基苯磺酰胺 、 原乙酸三乙酯 反应 12.0h， 以97%的产率得到ethyl N-(4-methoxyphenyl)sulfonylethanimidate
  参考文献：
  名称：

  Three-Component Reactions of Sulfonylimidates, Silyl Glyoxylates and N-tert-Butanesulfinyl Aldimines: An Efficient, Diastereoselective, and Enantioselective Synthesis of Cyclic N-Sulfonylamidines

  摘要：

  Three-component coupling reactions of sulfonylimidates, silyl glyoxylates and N-tert-butanesulfinyl aldimines efficiently provide cyclic N-sulfonylamiclines containing free endocyclic N-H. The formation of two C-C bonds (contiguous stereogenic carbons), one O-Si bond, and one C-N bond, together with the cleavage of the chiral auxiliary (tert-butanesulfinyl group), occurs with excellent chemoselectivity, diastereoselectivity, and enantioselectivity in this one-pot cascade transformation.

  DOI：

  10.1021/ol201029b

文献信息

• Three-Component Reactions of Sulfonylimidates, Silyl Glyoxylates and <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines: An Efficient, Diastereoselective, and Enantioselective Synthesis of Cyclic <i>N</i>-Sulfonylamidines
  作者：Ming Yao、Chong-Dao Lu

  DOI：10.1021/ol201029b

  日期：2011.5.20

  Three-component coupling reactions of sulfonylimidates, silyl glyoxylates and N-tert-butanesulfinyl aldimines efficiently provide cyclic N-sulfonylamiclines containing free endocyclic N-H. The formation of two C-C bonds (contiguous stereogenic carbons), one O-Si bond, and one C-N bond, together with the cleavage of the chiral auxiliary (tert-butanesulfinyl group), occurs with excellent chemoselectivity, diastereoselectivity, and enantioselectivity in this one-pot cascade transformation.