1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea hydrochloride | 1345266-06-9

• 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: 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea hydrochloride
• 英文别名: 1-[(1R,2R)-2-aminocyclohexyl]-3-[3,5-bis(trifluoromethyl)phenyl]thiourea;hydrochloride
• CAS: 1345266-06-9
• 化学式: C₁₅H₁₇F₆N₃S*ClH
• 分子量: 421.837
• InChiKey: RCCRSJINHVORMA-MNMPKAIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82.2
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-二叔丁基水杨醛 、 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea hydrochloride 在 potassium carbonate 作用下， 以 水 、 乙醇 为溶剂， 反应 2.75h， 以70%的产率得到(1R,2R)-2-{(E)-[3,5-di(tert-butyl)-2-hydroxyphenyl]methylideneamino}cyclohexylamino-3,5-bis(trifluoromethyl)anilinomethanethione
  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
• 作为产物：
  描述：

  间二(三氟甲基)苯胺 在 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 40.0h， 生成 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea hydrochloride
  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

文献信息

• Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN
  作者：Zhiguo Zhang、Katharina M. Lippert、Heike Hausmann、Mike Kotke、Peter R. Schreiner

  DOI：10.1021/jo201864e

  日期：2011.12.2

  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.