(1S,2R)-(OH)(C10H6)CHN(CHPh)2OH | 1383616-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2R)-(OH)(C10H6)CHN(CHPh)2OH
• 英文别名: 1-[[(1R,2S)-2-hydroxy-1,2-diphenylethyl]iminomethyl]naphthalen-2-ol
• CAS: 1383616-95-2
• 化学式: C₂₅H₂₁NO₂
• 分子量: 367.447
• InChiKey: WKZBYHOPFGZIEW-RPBOFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  titanium(IV) isopropylate 、 (1S,2R)-(OH)(C10H6)CHN(CHPh)2OH 以 二氯甲烷 为溶剂， 生成 ((1S,2R)-O(C10H6)CHN(CHPh)2O)Ti(Oi-Pr)2(HOi-Pr)
  参考文献：
  名称：

  Titanium complexes of chiral amino alcohol derived Schiff bases as efficient catalysts in asymmetric oxidation of prochiral sulfides with hydrogen peroxide as an oxidant

  摘要：

  An efficient asymmetric oxidation of prochiral sulfides catalyzed by a series of simple in situ generated complexes based on chiral amino alcohol derived Schiff bases with Ti(Oi-Pr)(4) was carried out in presence of cheap and environmentally benign oxidant H2O2 at 0 degrees C. Prochiral sulfides were converted to respective chiral sulfoxides efficiently (conversion, 93%; up to ee, 98%) with this system in 10 h at 0 degrees C. The present study demonstrated a significant role of steric influence of the substituent attached on both aryl and alkyl moiety on the enantioselectivity. Kinetic studies of the catalytic reaction showed first order dependence on substrate and catalyst whereas it is zero for the oxidant. Kinetic studies in combination with UV-vis. spectral studies were used to propose a catalytic cycle for the sulfoxidation reaction. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.04.014
• 作为产物：
  描述：

  (1S,2R)-2-氨基-1,2-二苯基乙醇 、 2-羟基-1-萘甲醛 在 sodium sulfate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以94%的产率得到(1S,2R)-(OH)(C10H6)CHN(CHPh)2OH
  参考文献：
  名称：

  Titanium complexes of chiral amino alcohol derived Schiff bases as efficient catalysts in asymmetric oxidation of prochiral sulfides with hydrogen peroxide as an oxidant

  摘要：

  An efficient asymmetric oxidation of prochiral sulfides catalyzed by a series of simple in situ generated complexes based on chiral amino alcohol derived Schiff bases with Ti(Oi-Pr)(4) was carried out in presence of cheap and environmentally benign oxidant H2O2 at 0 degrees C. Prochiral sulfides were converted to respective chiral sulfoxides efficiently (conversion, 93%; up to ee, 98%) with this system in 10 h at 0 degrees C. The present study demonstrated a significant role of steric influence of the substituent attached on both aryl and alkyl moiety on the enantioselectivity. Kinetic studies of the catalytic reaction showed first order dependence on substrate and catalyst whereas it is zero for the oxidant. Kinetic studies in combination with UV-vis. spectral studies were used to propose a catalytic cycle for the sulfoxidation reaction. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.04.014