1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-(5-phenyl-1H-imidazol-1-yl)cyclohexyl)thiourea | 1345265-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-(5-phenyl-1H-imidazol-1-yl)cyclohexyl)thiourea
• 英文别名: 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1R,2R)-2-(5-phenylimidazol-1-yl)cyclohexyl]thiourea
• CAS: 1345265-65-7
• 化学式: C₂₄H₂₂F₆N₄S
• 分子量: 512.522
• InChiKey: ZBBCPZWJQVRSQB-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (R,R)-N,N'-dibenzylidene-1,2-diaminocyclohexane 在 盐酸 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 122.0h， 生成 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-(5-phenyl-1H-imidazol-1-yl)cyclohexyl)thiourea
  参考文献：
  名称：

  Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN

  摘要：

  We report a new thiourea-Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enamioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.

  DOI：

  10.1021/jo201864e
• 作为试剂：
  描述：

  三甲基氰硅烷 、 正辛醛 在 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-(5-phenyl-1H-imidazol-1-yl)cyclohexyl)thiourea 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 2-((trimethylsilyl)oxy)nonanenitrile
  参考文献：
  名称：

  Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN

  摘要：

  We report a new thiourea-Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enamioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.

  DOI：

  10.1021/jo201864e