tert-butyl (2-cyano-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)carbamate | 1192815-59-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-butyl (2-cyano-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)carbamate
• CAS: 1192815-59-0
• 化学式: C₂₂H₃₂N₂O₃
• 分子量: 372.508
• InChiKey: ZSNUJKKCYBFQGN-WDYCEAGBSA-N

物化性质

• 熔点：
  69 °C
• 沸点：
  454.7±40.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.35
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  L-缬氨醇 、 tert-butyl (2-cyano-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)carbamate 在 zinc(II) chloride 、 ammonium hydroxide 作用下， 以 氯苯 、 水 为溶剂， 反应 20.5h， 以69%的产率得到2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)aniline
  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
• 作为产物：
  描述：

  tert-butyl (2-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)carbamate 、 氰酸苯酯 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 以77%的产率得到tert-butyl (2-cyano-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)carbamate
  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