N-[2-[(4R)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]naphthalen-1-yl]benzenesulfonamide | 1192815-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-[(4R)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]naphthalen-1-yl]benzenesulfonamide
• CAS: 1192815-33-0
• 化学式: C₂₂H₂₂N₂O₃S
• 分子量: 394.494
• InChiKey: GITXPAISOHYFJO-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 苯磺酰氯 在 吡啶 、 4-二甲氨基吡啶 、 甲醇 、 potassium carbonate 作用下， 生成 N-[2-[(4R)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]naphthalen-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Toolbox Approach to the Search for Effective Ligands for Catalytic Asymmetric Cr-Mediated Coupling Reactions

  摘要：

  Chromium catalysts derived from chiral sulfonamides represented by A effect the couplings of aldehydes with vinyl, allyl, or alkyl halides. With three distinct sites for structural modification, A affords access to a structurally diverse pool of chiral sulfonamides. The Cr catalysts derived from these sulfonamides exhibit a broad range of catalyst-substrate matching profiles. A strategy is presented to search for a satisfactory chiral sulfonamide for a given substrate. In order to demonstrate the generality and effectiveness of this approach, five diverse C-C bond-forming cases have been selected from the halichondrin synthesis. For each of the cases, two ligands have been deliberately searched for, to induce the formation of (R)and (S)-alcohols, respectively, at the arbitrarily chosen efficiency level of ">= 80% yield with >= 20:1 stereoselectivity in the presence of <= 20 mol % of a Cr catalyst". For 9 out of the 10 cases studied, a satisfactory catalyst has been found within this pool of sulfonamides. Even for the remaining case, a Cr catalyst inducing stereoselectivity up to 8:1 has been identified.

  DOI：

  10.1021/ja905843e
• 作为试剂：
  描述：

  艾日布林-2碘 、 3-((2S,5S)-3-methylene-5-(3-(t-butyldiphenylsilyloxy)propyl)tetrahydrofuran-2-yl)propanal 在 chromium dichloride 、 锰 、 二氯二茂锆 、 cobalt(II) phthalocyanine 、 N-[2-[(4R)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]naphthalen-1-yl]benzenesulfonamide 、 1,8-双二甲氨基萘 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 36.0h， 生成 (3S,5R)-1-{(2S,5S)-5-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-3-methylene-tetrahydro-furan-2-yl}-6-iodo-5-methyl-hept-6-en-3-ol 、 (3R,5R)-1-{(2S,5S)-5-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-3-methylene-tetrahydro-furan-2-yl}-6-iodo-5-methyl-hept-6-en-3-ol
  参考文献：
  名称：

  Toolbox Approach to the Search for Effective Ligands for Catalytic Asymmetric Cr-Mediated Coupling Reactions

  摘要：

  Chromium catalysts derived from chiral sulfonamides represented by A effect the couplings of aldehydes with vinyl, allyl, or alkyl halides. With three distinct sites for structural modification, A affords access to a structurally diverse pool of chiral sulfonamides. The Cr catalysts derived from these sulfonamides exhibit a broad range of catalyst-substrate matching profiles. A strategy is presented to search for a satisfactory chiral sulfonamide for a given substrate. In order to demonstrate the generality and effectiveness of this approach, five diverse C-C bond-forming cases have been selected from the halichondrin synthesis. For each of the cases, two ligands have been deliberately searched for, to induce the formation of (R)and (S)-alcohols, respectively, at the arbitrarily chosen efficiency level of ">= 80% yield with >= 20:1 stereoselectivity in the presence of <= 20 mol % of a Cr catalyst". For 9 out of the 10 cases studied, a satisfactory catalyst has been found within this pool of sulfonamides. Even for the remaining case, a Cr catalyst inducing stereoselectivity up to 8:1 has been identified.

  DOI：

  10.1021/ja905843e