(2S,4S)-2,4-bis(methoxymethyl)azetidine | 168647-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (2S,4S)-2,4-bis(methoxymethyl)azetidine
• CAS: 168647-94-7
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: UAQLTWDMJLVJRE-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2,4-bis(methoxymethyl)azetidine 在 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 42.0h， 生成 N-(2,2-diphenyl-2-hydroxyethyl)-(S,S)-2,4-bis(methoxymethyl)azetidine
  参考文献：
  名称：

  Chiral C2-symmetric 2,4-disubstituted azetidines as chiral ligands in the addition of diethylzinc to aldehydes

  摘要：

  Chiral C-2-symmetric 2,4-disubstituted azetidine derivatives having a beta-amino alcohol moiety have been successfully synthesized and their stereoselective catalytic abilities have been examined in the asymmetric addition of diethylzinc to aldehydes in hexane. When N-(2,2-diphenyl-2-hydroxyethyl)-(S,S)-2,4-bis(methoxymethyl)azetidine 12 was used as a catalytic chiral ligand, the production of sec-alcohols having an S-absolute configuration could be achieved in high chemical yields (92-99%) and high enantiomeric excesses (83-93% for arylaldehydes and 63-65% for aliphatic aldehydes). For some arylaldehydes, the enantioselectivities are higher than the corresponding chiral C-2-symmetric 2,5-disubstituted pyrrolidine ligands. However, when the chiral C-2-symmetric azetidine derivatives 13 and 14, which have bulky substituents on the 2,4-positions were used as the chiral ligands under the same reaction conditions, the enantiomeric excesses of the corresponding sec-alcohols decreased to 20-30%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00186-x
• 作为产物：
  描述：

  (2S,4S)-1-<(S)-1-phenylethyl>-2,4-bis(hydroxymethyl)azetidine 以71%的产率得到
  参考文献：
  名称：

  Hoshino Junichi, Hiraoka Junko, Hata Yasuo, Sawada Seiji, Yamamoto Yukio, J. Chem. Soc. Perkin Trans. 1, (1995) N 6, S 12

  摘要：

  DOI：

文献信息

• Hoshino, Jun'ichi; Hiraoka, Junko; Hata, Yasuo, Journal of the Chemical Society. Perkin transactions I, 1995, # 6, p. 693 - 698
  作者：Hoshino, Jun'ichi、Hiraoka, Junko、Hata, Yasuo、Sawada, Seiji、Yamamoto, Yukio

  DOI：——

  日期：——
• Hoshino Junichi, Hiraoka Junko, Hata Yasuo, Sawada Seiji, Yamamoto Yukio, J. Chem. Soc. Perkin Trans. 1, (1995) N 6, S 12
  作者：Hoshino Junichi, Hiraoka Junko, Hata Yasuo, Sawada Seiji, Yamamoto Yukio

  DOI：——

  日期：——
• Chiral C2-symmetric 2,4-disubstituted azetidines as chiral ligands in the addition of diethylzinc to aldehydes
  作者：Min Shi、Jian-Kang Jiang

  DOI：10.1016/s0957-4166(99)00186-x

  日期：1999.5

  Chiral C-2-symmetric 2,4-disubstituted azetidine derivatives having a beta-amino alcohol moiety have been successfully synthesized and their stereoselective catalytic abilities have been examined in the asymmetric addition of diethylzinc to aldehydes in hexane. When N-(2,2-diphenyl-2-hydroxyethyl)-(S,S)-2,4-bis(methoxymethyl)azetidine 12 was used as a catalytic chiral ligand, the production of sec-alcohols having an S-absolute configuration could be achieved in high chemical yields (92-99%) and high enantiomeric excesses (83-93% for arylaldehydes and 63-65% for aliphatic aldehydes). For some arylaldehydes, the enantioselectivities are higher than the corresponding chiral C-2-symmetric 2,5-disubstituted pyrrolidine ligands. However, when the chiral C-2-symmetric azetidine derivatives 13 and 14, which have bulky substituents on the 2,4-positions were used as the chiral ligands under the same reaction conditions, the enantiomeric excesses of the corresponding sec-alcohols decreased to 20-30%. (C) 1999 Elsevier Science Ltd. All rights reserved.