(S)-naphthalen-2-yl-[oxido-bis(2,2,2-trifluoroethoxy)phosphaniumyl]methanol | 1045892-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-naphthalen-2-yl-[oxido-bis(2,2,2-trifluoroethoxy)phosphaniumyl]methanol
• CAS: 1045892-62-3
• 化学式: C₁₅H₁₃F₆O₄P
• 分子量: 402.23
• InChiKey: GFRRCMASTVEYEX-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  bis(2,2,2-trifluoroethyl)phosphite 、 2-萘甲醛 在 C₆₄H₆₀AlClN₂O₂ 作用下， 以 正己烷 为溶剂， 反应 0.33h， 以98%的产率得到(S)-naphthalen-2-yl-[oxido-bis(2,2,2-trifluoroethoxy)phosphaniumyl]methanol
  参考文献：
  名称：

  Catalytic Enantioselective Pudovik Reaction of Aldehydes and Aldimines with Tethered Bis(8-quinolinato) (TBOx) Aluminum Complex

  摘要：

  New chiral tethered bis(8-quinolinolato) (TBOx) aluminum(III) complexes effectively catalyze the addition of phosphites to aldehydes and aldimines to give enantioenriched alpha-hydroxy and a-amino phosphonates in high yields and enantioselectivities with unprecedented reactivity (TON = 100 as high as 200). The catalyst is optimized with the low catalyst loading of 0.5 - 1.0 mol %. The modular synthesis of the catalyst allows for potential to tune the reaction for maximum catalytic activity. To date there are few examples with broad substrate scopes that can catalyze both aldehydes and aldimines with such high selectivity and no reports utilizing such low catalyst loading.

  DOI：

  10.1021/ja803859p