diphenyl-[1-((1S)-phenylethyl)azetidin-(2R)-yl]methanol

• 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: diphenyl-[1-((1S)-phenylethyl)azetidin-(2R)-yl]methanol
• 英文别名: diphenyl-[(2R)-1-[(1S)-1-phenylethyl]azetidin-2-yl]methanol
• 化学式: C₂₄H₂₅NO
• 分子量: 343.469
• InChiKey: SGRXPZXZFVLCLR-WMZHIEFXSA-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：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯基溴化镁 、 methyl (2R,1'S)-1-(1'-methyl)benzylazetidine-2-carboxylate 在 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到diphenyl-[1-((1S)-phenylethyl)azetidin-(2R)-yl]methanol
  参考文献：
  名称：

  Enantioselective addition of alkynylzinc to arylaldehydes catalyzed by azetidino amino alcohols bearing an additional stereogenic center

  摘要：

  Chiral azetidino amino alcohol ligands bearing an additional stereogenic center were readily prepared and used as catalysts for the asymmetric addition of alkynylzinc to aromatic aldehydes with enantioselectivities of up to 87% ee. The relationship between the reaction enantioselectivity and the structure of the chiral ligands was also evaluated in this reaction. The experimental results showed that the enantioselectivity level of the reaction was greatly influenced by the second stereogenic center attached to azetidine ring, but the stereochemical sense was only determined by the configuration of the azetidine ring. A possible transition structure for the catalytic asymmetric addition was also proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.031

文献信息

• Azetidine based ligands in boron catalyzed asymmetric Diels-Alder reactions
  作者：Wim A.J. Starmans、Richard W.A. Walgers、Lambertus Thijs、René de Gelder、Jan M.M. Smits、Binne Zwanenburg

  DOI：10.1016/s0040-4020(98)00204-x

  日期：1998.5

  The preparation of a new class of azetidine-based auxiliaries and their selectivity in the BBr3 catalyzed Diets-Alder reaction is described. The results are compared with a similar proline-derived ligand and a known prolinol auxiliary. Results show that selectivities are highly dependent on the dienophile and the substituent of the chiral auxiliary. (C) 1998 Elsevier Science Ltd. All rights reserved.