N-(2-methylpropenoyl)-1,8-naphthosultam | 405114-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-methylpropenoyl)-1,8-naphthosultam
• 英文别名: 1-(2,2-Dioxo-2lambda6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-3-yl)-2-methylprop-2-en-1-one；1-(2,2-dioxo-2λ6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-3-yl)-2-methylprop-2-en-1-one
• CAS: 405114-66-1
• 化学式: C₁₄H₁₁NO₃S
• 分子量: 273.312
• InChiKey: SWWVCEYZHLIPDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘代叔丁烷 、 N-(2-methylpropenoyl)-1,8-naphthosultam 在 chiral cyclopropyl bisoxazoline 、 magnesium bromide 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 正己烷 为溶剂， 反应 2.5h， 生成 N-((2R),4,4-trimethylpentanoyl)-1,8-naphthosultam 、 N-((2S),4,4-trimethylpentanoyl)-1,8-naphthosultam
  参考文献：
  名称：

  The Role of the Achiral Template in Enantioselective Transformations. Radical Conjugate Additions to α-Methacrylates Followed by Hydrogen Atom Transfer

  摘要：

  We have evaluated various achiral templates (1a-g, 10, and 16) in conjunction with chiral Lewis acids in the conjugate addition of nucleophilic radicals to alpha-methacrylates followed by enantioselective H-atom transfer, Of these, a novel naphthosultam template (10) gave high enantioselectivity in the H-atom-transfer reactions with ee's up to 90%. A chiral Lewis acid derived from MgBr2 and bisoxazoline (2) gave the highest selectivity in the enantioselective hydrogen-atom-transfer reactions. Non-C-2 symmetric oxazolines (20-25) have also been examined as ligands, and of these, compound 25 gave optimal results (87% yield and 80% ee). Insights into rotamer control in alpha-substituted acrylates and the critical role of the tetrahedral sulfone moiety in realizing high selectivity are discussed.

  DOI：

  10.1021/ja016839b
• 作为产物：
  描述：

  1,8-萘磺内酰胺 、 甲基丙烯酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以87%的产率得到N-(2-methylpropenoyl)-1,8-naphthosultam
  参考文献：
  名称：

  The Role of the Achiral Template in Enantioselective Transformations. Radical Conjugate Additions to α-Methacrylates Followed by Hydrogen Atom Transfer

  摘要：

  We have evaluated various achiral templates (1a-g, 10, and 16) in conjunction with chiral Lewis acids in the conjugate addition of nucleophilic radicals to alpha-methacrylates followed by enantioselective H-atom transfer, Of these, a novel naphthosultam template (10) gave high enantioselectivity in the H-atom-transfer reactions with ee's up to 90%. A chiral Lewis acid derived from MgBr2 and bisoxazoline (2) gave the highest selectivity in the enantioselective hydrogen-atom-transfer reactions. Non-C-2 symmetric oxazolines (20-25) have also been examined as ligands, and of these, compound 25 gave optimal results (87% yield and 80% ee). Insights into rotamer control in alpha-substituted acrylates and the critical role of the tetrahedral sulfone moiety in realizing high selectivity are discussed.

  DOI：

  10.1021/ja016839b

文献信息

• The Role of the Achiral Template in Enantioselective Transformations. Radical Conjugate Additions to α-Methacrylates Followed by Hydrogen Atom Transfer
  作者：Mukund P. Sibi、Justin B. Sausker

  DOI：10.1021/ja016839b

  日期：2002.2.1

  We have evaluated various achiral templates (1a-g, 10, and 16) in conjunction with chiral Lewis acids in the conjugate addition of nucleophilic radicals to alpha-methacrylates followed by enantioselective H-atom transfer, Of these, a novel naphthosultam template (10) gave high enantioselectivity in the H-atom-transfer reactions with ee's up to 90%. A chiral Lewis acid derived from MgBr2 and bisoxazoline (2) gave the highest selectivity in the enantioselective hydrogen-atom-transfer reactions. Non-C-2 symmetric oxazolines (20-25) have also been examined as ligands, and of these, compound 25 gave optimal results (87% yield and 80% ee). Insights into rotamer control in alpha-substituted acrylates and the critical role of the tetrahedral sulfone moiety in realizing high selectivity are discussed.